Deale holiday homes

We found 183 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Deale that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a pool. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Deale

Showing deals for:18 Dec - 25 Dec

Exterior
Terrace/patio
Kitchen - Granite Island
Great Room
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
NZ$17,517
for 7 nights, 1 home
NZ$2,502 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Upstairs Hall
Porch Dining Table
Swimming Pool
Kitchen
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Harwood

8% off
NZ$23,335
for 7 nights, 1 home
NZ$3,334 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Living area
Private kitchen
Room
Living area
Exceptional
(13 reviews)

The General's House-Spacious Home w/Pool & Hot Tub

Annapolis

8% off
NZ$15,044
for 7 nights, 1 home
NZ$2,149 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Terrace/patio
Outdoor dining
Living area
Property grounds
Exceptional
(11 reviews)

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Huntingtown

8% off
NZ$6,292
for 7 nights, 1 cottage
NZ$899 per night
includes taxes & fees
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Dining
Living area
Exterior
Private kitchen
Exceptional
(7 reviews)

Waterfront- 5-bedroom house with dock in charming North Beach

North Beach

8% off
NZ$13,993
for 7 nights, 1 home
NZ$1,999 per night
includes taxes & fees
Waterfront- 5-bedroom house with dock in charming North Beach
Beautiful North Bach, MD
Beautiful North Beach, MD
Open-concept living area and kitchen
Directly next door to Sunrise Garden park
Exceptional
(21 reviews)

Unbelievable beach views for 6

North Beach

8% off
NZ$4,593
for 7 nights, 1 apartment
NZ$656 per night
includes taxes & fees
Unbelievable beach views for 6
Living area
Living area
Dining
Interior
Exceptional
(11 reviews)

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Riva

8% off
NZ$7,185
for 7 nights, 1 home
NZ$1,026 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Interior
Room
Private kitchen
Interior
Exceptional
(17 reviews)

Bay Charm. 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil!

Prince Frederick

8% off
NZ$3,668
for 7 nights, 1 home
NZ$524 per night
includes taxes & fees
Bay Charm. 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil!
Exterior
Foyer
Room
Property grounds
Exceptional
(27 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
NZ$2,485
for 7 nights, 1 apartment
NZ$355 per night
includes taxes & fees
Guest Quarters at the Inn - 102
Exterior
Interior
Marina
Interior
Exceptional
(55 reviews)

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

West River

12% off
NZ$2,208
for 7 nights, 1 cottage
NZ$315 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Exterior
Foyer
Room
Living area
Exceptional
(21 reviews)

Guest quarters at the inn - 205

North Beach

8% off
NZ$3,043
for 7 nights, 1 apartment
NZ$435 per night
includes taxes & fees
Guest quarters at the inn - 205
Room
Foyer
Exterior
Bathroom
Exceptional
(18 reviews)

Guest Quarters at the Inn - 101

North Beach

8% off
NZ$2,485
for 7 nights, 1 apartment
NZ$355 per night
includes taxes & fees
Guest Quarters at the Inn - 101
Room
Interior
bedroom with queen and smart tv
Room
Exceptional
(28 reviews)

Tranquility Awaits

Annapolis

16% off
NZ$2,029
for 7 nights, 1 apartment
NZ$290 per night
includes taxes & fees
Tranquility Awaits
Exterior
Foyer
Room
Property grounds
Exceptional
(20 reviews)

Guest quarters at the inn - 204

North Beach

8% off
NZ$3,043
for 7 nights, 1 apartment
NZ$435 per night
includes taxes & fees
Guest quarters at the inn - 204
Room
Foyer
Property grounds
Exterior
Exceptional
(32 reviews)

Guest Quarters at the Inn - 103

North Beach

8% off
NZ$2,485
for 7 nights, 1 apartment
NZ$355 per night
includes taxes & fees
Guest Quarters at the Inn - 103

  • 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

Friendly Deale will entice you

Enjoy the live music and other features of Deale. Revered for its bars, lake and shopping, this city is both welcoming and relaxing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Deale

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Deale a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Chesapeake Beach Water Park (5.9 mi / 9.6 km)
  • Thanksgiving Farm Wines (7.5 mi / 12.1 km)
  • Renditions Golf Club (11 mi / 17.7 km)
  • Maryland Renaissance Festival (15.4 mi / 24.8 km)
  • South River Golf Links (9.9 mi / 15.9 km)
  • Lake Presidential Golf Club (10.6 mi / 17 km)

Exploring the natural landscape of Deale

Whether you're an active traveller or just want to spend some time taking in the scenery, Deale is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Triton Beach (8.1 mi / 13 km)
  • Breezy Point Beach (11 mi / 17.7 km)
  • Maryland Quiet Waters Park (12 mi / 19.3 km)
  • Bay Ridge Beach (12.9 mi / 20.8 km)
  • Allen Pond Park (14.6 mi / 23.4 km)
  • Northern Chesapeake Bay (17.2 mi / 27.7 km)

How to get to and around Deale

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 24.2 mi (38.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into College Park, MD (CGS), which is 24.3 mi (39.1 km) away.

Frequently asked questions

What is the best area to stay in Deale when booking a holiday rental?
When considering a holiday rental in Deale, Maryland, the best area to stay would be near the waterfront, particularly along the scenic shoreline that offers stunning views of the Chesapeake Bay. This area is not only picturesque but also provides easy access to some of the town's charming attractions. For instance, you can visit the local parks where you can enjoy leisurely walks or picnics, and the nearby marinas are superb for those who enjoy boating or fishing.In terms of properties, the waterfront area typically has a variety of options ranging from quaint cottages to more spacious family homes, allowing visitors to find something that suits their needs. Additionally, being close to the heart of Deale means you'll have easy access to delightful seafood restaurants and local shops that showcase the community's maritime heritage.
Where are the best areas for renting a beach house in Deale?
For renting a beach house in Deale, Maryland, the areas along the Chesapeake Bay offer picturesque settings ideal for a relaxing getaway. The waterfront neighbourhoods near the Deale Beach area are particularly popular, featuring properties that typically include amenities such as private docks, spacious decks for outdoor dining, and access to sandy beaches. Many of these homes are designed for family gatherings, often boasting fully equipped kitchens and ample living space, superb for entertaining.The nearby Herrington Harbour offers additional options, where beach houses come with features like pools, hot tubs, and stunning bay views. This marina community is also known for its vibrant setting, with local shops and restaurants nearby, providing convenience for travellers.Exploring the area, visitors can enjoy water activities such as kayaking, fishing, and boating, with many rentals situated close to launch points. Moreover, the scenic trails and parks in the vicinity, such as the nearby Calvert Cliffs State Park, offer opportunities for hiking and enjoying the natural beauty of the region.
What is the most popular type of holiday rental accomodation in Deale?
In Deale, holiday houses are the most popular type of holiday rental, with around 12 available throughout the area. These properties typically feature several bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups looking to enjoy a home-like environment. Additionally, various cottages can be found, providing a charming and cosy atmosphere for those seeking a more intimate stay. Many of these rentals also include outdoor spaces such as patios or gardens, superb for relaxing after a day of exploring the nearby waterfront or local parks.
Are there any family house rentals in Deale?
In Deale, Maryland, there are several family-friendly house rentals available, making it a splendid choice for those travelling with children. The homes in this coastal locale typically feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces ideal for relaxation or play. Many properties also include amenities such as Wi-Fi and air conditioning to enhance the comfort of your stay.Families will appreciate the proximity to the Chesapeake Bay, where opportunities for fishing, boating, and beach outings abound. The nearby parks and nature trails offer excellent options for outdoor activities, ensuring that visitors can enjoy both the serene environment and local attractions.
Can I rent a holiday home with a pool or hot tub in Deale?
In Deale, Maryland, there are several holiday homes available for rent that come equipped with pools and hot tubs, providing a fantastic option for relaxation during your stay. This charming coastal town offers a mix of waterfront properties and homes located within the scenic surroundings of the Chesapeake Bay. Many rentals feature private pools and hot tubs, along with outdoor spaces great for entertaining or enjoying the peaceful evenings. Travellers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor patios, enhancing the overall experience.
Are there pet-friendly house rentals in Deale?
In Deale, Maryland, there are several pet-friendly holiday house rentals available for those looking to enjoy a getaway with their furry friends. Many of these properties are situated close to the waterfront, offering stunning views and easy access to the Chesapeake Bay. Travellers can expect amenities such as spacious backyards, outdoor seating areas for relaxation, and fully equipped kitchens to prepare meals after a day of exploring.The nearby area of Deale also features a variety of parks and natural spaces that are suitable for pets, making it a great choice for pet owners. The local beaches and waterfront parks provide opportunities for walks and playtime, ensuring that both pets and their owners have a delightful experience.
Are there any remote work holiday rentals in Deale?
In Deale, Maryland, there are several remote work holiday rentals available, with around 15 options to choose from. This charming waterfront community offers a relaxing atmosphere while still providing the necessary amenities for working remotely. Many of the properties feature dedicated workspaces or desks, high-speed Wi-Fi, and access to printers, ensuring that guests can maintain productivity during their stay.Deale is known for its scenic views of the Chesapeake Bay, and many rentals have outdoor spaces where you can unwind after a day of work, such as patios or balconies. The area is also close to local attractions like the nearby Sandy Point State Park, which offers beautiful trails and picnic areas, great for taking breaks and enjoying nature. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Deale?
In Deale, popular rental amenities typically include kitchens, allowing guests to prepare their own meals, and outdoor spaces such as decks, patios, or balconies where they can enjoy the pleasant surroundings. Many properties also feature fireplaces, providing a warm and inviting atmosphere, especially during cooler evenings.
What are the top attractions in Deale?
In Deale, Maryland, visitors can enjoy a charming coastal atmosphere with several attractions to explore. The Deale area is renowned for its beautiful waterfront views and recreational activities, particularly along the Chesapeake Bay. One of the highlights is the picturesque Deale Beach, which offers opportunities for swimming, picnicking, and enjoying the serene surroundings.For those interested in local culture, the nearby Captain Avery Museum showcases the maritime history of the area and features various exhibits related to the Chesapeake Bay. The museum is situated in a quaint setting and often hosts community events and activities.Fishing enthusiasts can take advantage of the many charter services available in the area, providing access to the rich fishing grounds of the bay. Additionally, the local marinas offer boat rentals, making it easy for visitors to explore the beautiful waterways.Nature lovers will appreciate the nearby Broadneck Park, which features walking trails, sports fields, and playgrounds, great for family outings.
Are all fees included in the Deale 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 Deale holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Deale 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 Deale holiday homes?
You can find great discounts on holiday homes in Deale 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 Deale holiday home booking on Bookabach?
To find Deale 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 Deale?
A long-stay holiday home in Deale 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 Deale holiday home?
Book your Deale 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 Deale?
Prices for holiday homes in Deale 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 Deale 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.