Annapolis holiday homes

We found 710 holiday rentals — enter your dates for availability
Select from 381 houses, 46 apartments and other holiday rentals to find the perfect place for your stay in Annapolis. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Annapolis

Showing deals for:1 Jan - 8 Jan

Interior
Private kitchen
Dining
Room
Exceptional
(21 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

15% off
NZ$7,516
for 7 nights, 1 home
NZ$1,074 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Swimming Pool
Porch Dining Table
Upstairs Hall
Kitchen
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Harwood

7% off
NZ$26,106
for 7 nights, 1 home
NZ$3,729 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
POOL TABLE, TENNIS/PICKLE BALL RACKETS, BEACH SUPPLIES, BOARD GAMES, MOVIES
FAMILY ROOM W/FIREPLACE & FLAT SCREEN TV
LARGE OPEN KITCHEN
SCREENED PORCH
Exceptional
(48 reviews)

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis

12% off
NZ$11,025
for 7 nights, 1 home
NZ$1,575 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Marina
Terrace/patio
Living room with wood fireplace and second TV with basic channels
outdoor space
Exceptional
(94 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

8% off
NZ$6,843
for 7 nights, 1 home
NZ$978 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Exterior
Terrace/patio
The Green Bedroom View
Great Room
Exceptional
(16 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
NZ$19,471
for 7 nights, 1 home
NZ$2,782 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Interior
New Kitchen 2022
Exterior
Dining room
Exceptional
(66 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
NZ$5,866
for 7 nights, 1 home
NZ$838 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Kitchen
Kitchen
Kitchen
Kitchen
Exceptional
(32 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off
NZ$3,883
for 7 nights, 1 room
NZ$555 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Private kitchen
Living area
Interior
Exterior
Exceptional
(52 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
NZ$11,674
for 7 nights, 1 home
NZ$1,668 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Living area
Private kitchen
Dining
Exterior
Excellent
(12 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
NZ$6,420
for 7 nights, 1 home
NZ$917 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Lawn for yard games along the waterfront, or simply relax in the shade
Enjoy screened in porch with dining table and sitting area
Beautiful waterfront home on Burley Creek with private pier
West-facing screened porch with bar area and café lights for night ambience
Exceptional
(64 reviews)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis

8% off
NZ$6,906
for 7 nights, 1 home
NZ$987 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Private kitchen
Interior
Exterior
Exterior
Exceptional
(15 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
NZ$7,672
for 7 nights, 1 home
NZ$1,096 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Interior
Interior
Marina
Interior
Exceptional
(56 reviews)

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River

12% off
NZ$2,311
for 7 nights, 1 cottage
NZ$330 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Master bedroom suite w/ private covered balcony
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Dining
Private kitchen
Exceptional
(78 reviews)

Charming Annapolis WaterVIEW Home

Annapolis

11% off
NZ$5,843
for 7 nights, 1 home
NZ$835 per night
includes taxes & fees
Charming Annapolis WaterVIEW Home
Interior
Private kitchen
Interior
Living area
Exceptional
(11 reviews)

Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok

Annapolis

7% off
NZ$14,333
for 7 nights, 1 home
NZ$2,048 per night
includes taxes & fees
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
Private kitchen
Terrace/patio
Dining
Exterior
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
NZ$4,119
for 7 nights, 1 home
NZ$588 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Outdoor dining
Pool
Interior
Property grounds
Exceptional
(218 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

12% off
NZ$5,931
for 7 nights, 1 room
NZ$847 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Local artwork is displayed and for sale, if you wish to take a memory home.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Twin size sofa/futon for a 3rd person.
Room
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
NZ$3,150
for 7 nights, 1 apartment
NZ$450 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Outdoor dining
Dining
Living area
Private kitchen
Exceptional
(34 reviews)

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis

8% off
NZ$8,586
for 7 nights, 1 home
NZ$1,227 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Dining room table
String lights on the patio make it the perfect place to unwind in the evening!
Kitchen with island
Welcome!
Exceptional
(23 reviews)

***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.

Annapolis

8% off
NZ$6,697
for 7 nights, 1 home
NZ$957 per night
includes taxes & fees
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
Walking distance to gate 3
City Dock
Terrace/patio
Kitchen/lounging/dining room
Exceptional
(35 reviews)

Gem in Downtown Annapolis, close to USNA, St. John's College

Annapolis

8% off
NZ$5,728
for 7 nights, 1 home
NZ$818 per night
includes taxes & fees
Gem in Downtown Annapolis, close to USNA, St. John's College
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Comfortable family room with reclining sofa, Smart TV and remote controlled window shades.
Wonderful
(7 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
NZ$3,708
for 7 nights, 1 home
NZ$530 per night
includes taxes & fees
Cozy Cottage with Beach Access
enjoy the rockers on the porch while sipping on a cup of coffee
Exterior
Private kitchen
Property grounds
Exceptional
(12 reviews)

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis

7% off
NZ$5,070
for 7 nights, 1 home
NZ$724 per night
includes taxes & fees
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Water view from the kitchen
Property grounds
Private kitchen
Interior
Exceptional
(37 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
NZ$8,742
for 7 nights, 1 home
NZ$1,249 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Comfortable and cozy living room with fireplace (for aesthetic only), Smart TV, comfortable seating, games/puzzles, and books.
Updated kitchen with all major appliances
Private, fenced outdoor space
Dining room with space for 6
Exceptional
(9 reviews)

Timeless Charm Meets Modern Comfort

Annapolis

7% off
NZ$4,024
for 7 nights, 1 home
NZ$575 per night
includes taxes & fees
Timeless Charm Meets Modern Comfort
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Annapolis

  • Historic charm: Annapolis boasts a rich history with its beautifully preserved colonial architecture and vibrant downtown, perfect for leisurely exploration.
  • Waterfront activities: Enjoy scenic views and a range of water-based activities at the picturesque marinas and parks along the waterfront.
  • Cultural experiences: Immerse yourself in local culture through art galleries, museums, and community events that highlight Annapolis’s heritage.
  • Family-friendly atmosphere: The city offers numerous parks and family-oriented activities, making it an ideal destination for visitors of all ages.
  • Walkable city: Annapolis’s compact layout encourages visitors to explore on foot, discovering charming streets and hidden gems along the way.

Top attractions in Annapolis

Annapolis in Maryland offers a delightful blend of urban parks, marinas, and historic houses, perfect for a family or outdoor holiday. Explore its charming streets and immerse yourself in the city’s rich heritage and culture, all within a picturesque, walkable setting. Annapolis is ideal for travellers seeking a vibrant, historical city experience with plenty of opportunities for outdoor adventures.

  • Sandy Point Beach: Enjoy the beach vibes with splendid sandy shores perfect for a leisurely stroll or a refreshing dip in the water.
  • Annapolis Maritime Museum: Immerse yourself in local maritime culture, exploring maritime artefacts that tell the rich seafaring history of the city.
  • Bay Ridge Beach: Revel in the coastal charm with pristine beachscapes ideal for relaxation and scenic seaside moments.

Things to do recommended for couples

Experience the charm of Annapolis with a romantic harbour cruise, delightful waterfront dining and a leisurely stroll through historic streets, perfect for couples seeking a unique local escape.

Things to do recommended for families

Families can explore the historic waterfront at the Annapolis City Dock, enjoy a day at the sandy Broadneck Park beach, or take a scenic sailboat tour on the Chesapeake Bay. Don't miss the interactive exhibits at the Maryland State House for a fun learning experience.

Things to do recommended for groups

Groups visiting Annapolis can experience a fascinating historic tour of the U.S. Naval Academy, enjoy a delightful seafood feast at the waterfront, and take a scenic sailing trip on the Chesapeake Bay to soak in the stunning views of the coastline.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Annapolis

Whether you're journeying with a group, as a family, with your furry mates, or seeking extended stays, ensure you filter using the appropriate criteria. Here are some Vrbo booking pointers for you.

  • Traveling to Annapolis with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Annapolis with young kids: Traveling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Annapolis: For many, a family getaway wouldn't be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and comfortable beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Annapolis: If you're on the hunt for holiday rentals with great deals for stays of a month or more, you've come to the right spot. By using the right filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in and around Annapolis

Annapolis offers a rich historical vibe with its charming downtown and waterfront escape. Visitors can explore the city's storied streets, enjoy scenic views on the water, and immerse themselves in the family-friendly atmosphere that fills every neighbourhood. Whether you fancy a cultural stroll or a relaxing day by the water, Annapolis makes a brilliant destination for a memorable holiday experience.

  • Homewood: Homewood is a vibrant neighbourhood located in proximity to Annapolis, offering visitors a delightful blend of sports, culture, and outdoor experiences. This community is ideal for those looking to engage in educational pursuits, enjoy local shopping, or partake in recreational activities. Highlights include access to a renowned sports facility stadium, where you can catch exciting games, as well as a charming local academy that fosters a love for learning. The area is perfect for those keen on exploring the outdoors while soaking in the local culture.
  • Sherwood Forest: Nestled in the Annapolis area, Sherwood Forest is a picturesque village that caters to families and outdoor enthusiasts alike. Its inviting parks and green spaces offer a serene escape from the hustle and bustle of city life. Visitors can explore a nearby shopping centre for unique finds or enjoy recreational activities with family. The local urban park and stunning bay views provide ample opportunities for outdoor adventures, making it a perfect spot for picnics, hiking, and enjoying nature with loved ones.
  • Edgewater: Just 8km from Annapolis, Edgewater is a charming city that captivates visitors with its stunning scenery and family-friendly atmosphere. The area boasts beautiful beaches and access to the bay, making it a fantastic destination for outdoor activities such as swimming, kayaking, and fishing. With a variety of educational and recreational venues, including local shopping centres, Edgewater is an ideal spot for families seeking a fun-filled day out or a leisurely weekend getaway.

Best time to go to Annapolis

If you're planning a trip to Annapolis, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly Sunny
February37.9°F (3.3°C)Light RainMostly Sunny
March44.6°F (7.0°C)Light RainMostly Sunny
April55.0°F (12.8°C)Light RainMostly Sunny
May64.2°F (17.9°C)Light RainMostly Sunny
June73.0°F (22.8°C)Light RainMostly Sunny
July78.4°F (25.8°C)Light RainMostly Sunny
August76.8°F (24.9°C)Light RainMostly Sunny
September70.7°F (21.5°C)Light RainMostly Sunny
October60.4°F (15.8°C)Light RainMostly Sunny
November48.7°F (9.3°C)Light RainMostly Sunny
December41.5°F (5.3°C)Light RainMostly Sunny

Booking with Vrbo is simple

Are you looking to save on your next adventure? Being flexible with your travel dates could be a game changer, as prices can fluctuate. You might also unlock substantial savings by opting for a longer stay. To find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s innovative Trip Board offers you a place to build fresh itineraries, pick up where you last left off, or review and organise your plans. Any properties you’ve previously saved or booked are now neatly arranged in Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.bookabach.co.nz/trips

**Based on Vrbo properties bookings.

Historical Annapolis will entice you

The area's history and live music are just some of the reasons to come on holiday to Annapolis. Renowned for its university setting, shopping and restaurants, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Annapolis

Do you want to find attractions to see in the area? Venture out of your holiday home and check out everything that makes Annapolis a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bay Hills Golf Club (4.7 mi / 7.6 km)
  • Maryland Renaissance Festival (5.4 mi / 8.6 km)
  • Thanksgiving Farm Wines (10.4 mi / 16.8 km)
  • Renditions Golf Club (10.7 mi / 17.3 km)
  • Queenstown Harbor Golf (17.4 mi / 28 km)
  • St. Michaels Winery (19.9 mi / 32.1 km)

Exploring the natural landscape of Annapolis

Whether you're looking for adventure or just want to spend some time taking in the scenery, Annapolis is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (2.4 mi / 3.9 km)
  • Bay Ridge Beach (2.9 mi / 4.6 km)
  • Sandy Point Beach (5.7 mi / 9.2 km)
  • Northern Chesapeake Bay (8 mi / 12.8 km)
  • Fort Smallwood Park (11 mi / 17.6 km)
  • Eastern Neck National Wildlife Refuge (14.9 mi / 24 km)

Transport to and around Annapolis

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Baltimore Washington International Airport (BWI), which is 16.8 mi (27 km) away.

Frequently asked questions

What is the best area to stay in Annapolis when booking a holiday rental?
When considering a holiday rental in Annapolis, Maryland, the historic downtown area is one of the best choices. This charming neighbourhood is steeped in history and offers a vibrant setting, making it a favourite among visitors. Here, you'll find a delightful array of properties, from quaint cottages to elegant townhouses. The proximity to the waterfront is a major draw, allowing easy access to scenic views and leisurely strolls along the docks.One of the top attractions in downtown Annapolis is the Maryland State House, the oldest state capitol still in continuous use, which showcases stunning architecture and rich American history. Another highlight is the United States Naval Academy, where you can explore its beautiful grounds and learn about its storied tradition. The area's cobblestone streets are lined with charming boutiques, restaurants, and galleries, providing plenty of options for dining and shopping.If you prefer a more residential feel, Eastport is another excellent choice. This neighbourhood, just across the water from downtown, offers a mix of waterfront properties and cosy homes, along with a relaxed vibe. Eastport is known for its local eateries and boutique shops, and it's just a short walk or boat ride from the bustling downtown area.
Where are the best areas for renting a beach house in Annapolis?
For renting a beach house in Annapolis, the area around the Chesapeake Bay is highly desirable. The Eastport neighbourhood, located just across the water from downtown Annapolis, is particularly popular for its charming waterfront properties. Many rentals here offer stunning views of the bay, private docks, and easy access to local marinas, making them superb for those interested in boating or fishing. Guests can expect amenities such as spacious decks for outdoor dining, modern kitchens, and comfortable living areas, ideal for family gatherings or relaxing after a day on the water.Another great option is the Cape St. Claire community, which features a mix of traditional beach cottages and more modern homes. This area provides a laid-back atmosphere with access to sandy beaches and picnic areas, along with amenities like outdoor showers, fire pits, and community facilities. Visitors can enjoy local parks and trails, superb for walking or cycling, and the proximity to local shops and restaurants adds to the convenience.For those looking for a more secluded experience, the properties along Broadneck Park offer a tranquil setting with easy access to the bay. Rentals in this area often include features like large yards, private balconies, and family-friendly amenities, making them an excellent choice for travellers seeking a peaceful retreat while still being close to the attractions of Annapolis.
Are there any houseboat rentals in Annapolis?
In Annapolis, there are about 16 houseboat holiday rentals available, primarily located along the scenic waterfront and in marinas close to the historic district. These unique accommodations offer a blend of nautical charm and modern comfort, with most featuring amenities such as fully equipped kitchens, spacious living areas, and outdoor decks superb for enjoying the views of the Chesapeake Bay. Many houseboats are conveniently situated near popular attractions like the United States Naval Academy and the vibrant City Dock, allowing guests to immerse themselves in the local culture and dining options.
What is the most popular type of holiday rental accomodation in Annapolis?
In Annapolis, holiday houses are the most popular type of holiday rental, with around 1,204 available throughout the city. These properties are often located in charming neighbourhoods close to the historic district, providing easy access to attractions such as the United States Naval Academy and the waterfront. Most holiday houses come equipped with multiple bedrooms, spacious living areas, and fully equipped kitchens, allowing guests to enjoy a home-like experience.Apartments are also a top option, with approximately 180 available, typically featuring modern amenities and convenient locations near local shops and restaurants. For those seeking a great experience, there are about 88 cottages and 88 condos, which often provide picturesque views and outdoor spaces for relaxation. Additionally, a few houseboats are available for a distinctive stay on the water.
Are there any family house rentals in Annapolis?
In Annapolis, Maryland, there are numerous family-friendly house rentals available, with around 257 options throughout the city. This charming area is known for its maritime heritage, historic architecture, and vibrant waterfront, making it an excellent choice for families. Many properties in neighbourhoods such as Eastport and the Historic District offer spacious living areas, fully equipped kitchens, and outdoor spaces that are superb for children to enjoy.Visitors can find amenities like Wi-Fi, air conditioning, and sometimes even features such as game rooms or backyards with grills, enhancing the family experience. Moreover, being close to attractions like the U.S. Naval Academy, the Maryland State House, and the picturesque City Dock allows families to easily engage in educational and recreational activities together.
Can I rent a holiday home with a pool or hot tub in Annapolis?
In Annapolis, there are several holiday homes available for rent that feature pools and hot tubs, with around 38 options to choose from. This charming city, known for its maritime heritage and historic architecture, offers a variety of neighbourhoods where these properties can be found, including the picturesque Eastport area, which is close to the waterfront and offers stunning views, and the quaint Historic District, where visitors can explore cobblestone streets and local shops.Travellers can expect a range of amenities in these rentals, including private swimming pools, relaxing hot tubs, and spacious outdoor areas for entertaining. Many properties also come with fully equipped kitchens, allowing for convenient meal preparation, and some may feature additional luxuries such as outdoor dining spaces, fire pits, and easy access to local attractions.
Are there pet-friendly house rentals in Annapolis?
In Annapolis, there are numerous pet-friendly house rentals available, with around 149 options to choose from. The city offers a charming blend of historic architecture and waterfront views, making it a delightful destination for pet owners. Many holiday rentals come equipped with amenities such as spacious backyards, fully stocked kitchens, and comfortable living areas, allowing for a relaxing stay with your furry companions.The neighbourhood around the historic district is particularly appealing, with properties that provide easy access to local parks and the scenic waterfront. The nearby Quiet Waters Park features lovely walking trails and open spaces, superb for exercising pets, while the Broadneck Park offers additional recreational areas for outdoor activities. Additionally, the city's dog-friendly cafes and shops enhance the experience for travellers with pets, ensuring both comfort and convenience during their stay. See all pet-friendly rentals in Annapolis.
Are there any remote work holiday rentals in Annapolis?
In Annapolis, there are a significant number of remote work holiday rentals available, with around 1,492 options to choose from. This charming city, known for its rich maritime history and vibrant culture, provides an excellent backdrop for those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated workspaces or desks, and comfortable living areas that allow for a productive environment.Travellers can expect a variety of accommodations, ranging from quaint cottages to spacious homes, often featuring modern kitchens and outdoor spaces great for a break from work. The historic downtown area, with its picturesque streets and waterfront views, offers plenty of opportunities for relaxation after a day of remote working. Additionally, the proximity to local attractions such as the United States Naval Academy and the scenic Annapolis Harbor adds to the appeal. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Annapolis?
In Annapolis, popular rental amenities include well-equipped kitchens, which allow guests to prepare meals during their stay. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the pleasant Maryland weather. A coffee and tea maker is commonly found in rentals, ensuring visitors can enjoy their morning brew at their convenience. Onsite parking is another sought-after amenity, making it easier for guests to explore the historic downtown area and the scenic waterfront.
When is the best time to visit Annapolis for a holiday rental?
The best time to visit Annapolis for a holiday rental is during the peak season from May to July. This vibrant period is particularly popular among travellers looking to enjoy the city's rich maritime culture and beautiful waterfront. With warm temperatures averaging between 20 to 30 degrees Celsius, it's an ideal time for outdoor activities such as sailing, kayaking, and exploring the historic streets lined with charming shops and eateries.July stands out as the most popular month, attracting families and groups eager to experience the lively option created by festivals and events, including the renowned Annapolis Arts & Wine Festival. Visitors can take advantage of longer daylight hours to soak in the sights, making it a truly delightful experience.For those looking to maximise their budget while still enjoying the beauty of Annapolis, consider a trip in November. This month, while quieter, offers a unique charm with fewer crowds, allowing for leisurely strolls through the picturesque downtown and the chance to enjoy local dining without the rush of peak season.
What are the top attractions in Annapolis?
In Annapolis, visitors can take part in a rich maritime heritage and vibrant culture. The historic district is a must-see, featuring charming historic architecture and attractions like the Maryland State House, where the Continental Congress once met. Here, holiday rentals often reflect the area's history and provide easy access to local shops and restaurants.The United States Naval Academy is another key attraction, offering guided tours that showcase its impressive grounds and museums. Nearby, the scenic waterfront along City Dock is superb for leisurely strolls and dining, with stunning views of the boats and the Chesapeake Bay.For those who appreciate nature, Sandy Point State Park provides a beautiful setting for picnics, hiking, and beach activities, all just a short drive from the city centre.
Are all fees included in the Annapolis holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Annapolis holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Annapolis with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Annapolis holiday homes?
You can find great discounts on holiday homes in Annapolis on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Annapolis holiday home booking on Bookabach?
To find Annapolis holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Annapolis?
A long-stay holiday home in Annapolis is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Annapolis holiday home?
Book your Annapolis holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Annapolis?
Prices for holiday homes in Annapolis vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Annapolis to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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