Photo by Patricia Knorr

Chester holiday homes

We found 217 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Chester that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Chester

Showing deals for:8 Jan - 15 Jan

SuperMoon rising behind the house with moon beams on the bay
Interior
Interior
Dining
Exceptional
(47 reviews)

Sunset Lodge on the Bay

Rock Hall

9% off
NZ$14,343
for 7 nights, 1 home
NZ$2,049 per night
includes taxes & fees
Sunset Lodge on the Bay
Room
Private kitchen
Interior
Dining
Exceptional
(21 reviews)

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

Annapolis

16% off
NZ$7,988
for 7 nights, 1 home
NZ$1,141 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Room
Terrace/patio
Living area
Private kitchen
Exceptional
(5 reviews)

Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.

Stevensville

16% off
NZ$8,844
for 7 nights, 1 home
NZ$1,263 per night
includes taxes & fees
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Kent Island Beach House: 1,800 sq ft retreat located across from Beach Bar!
The owners enjoy the local wildlife. Local osprey & herons are always fishing.
Spacious modern well-lit kitchen with lots of counter space and furnishings.
KI Beach House has many Great Rooms for Mingling or just being by yourself.
Exceptional
(75 reviews)

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

8% off
NZ$10,278
for 7 nights, 1 home
NZ$1,468 per night
includes taxes & fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
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$10,818
for 7 nights, 1 home
NZ$1,545 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Exterior
New Kitchen 2022
Property grounds
Interior
Exceptional
(66 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
NZ$5,568
for 7 nights, 1 home
NZ$795 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Entrance from inside. Half bath on first floor is the door on the left.
Favorite night spot for my extended family, when we are there
Sunroom 1/2 - Great view of pond, Bay in distance. So much wildlife to see.
Stocked pantry, coffee station. Fridge/freezer + mud room fridge & freezer
Exceptional
(217 reviews)

240' Private Beachfront @Kent Island Love Point - Great for Families

Stevensville

19% off
NZ$5,865
for 7 nights, 1 home
NZ$838 per night
includes taxes & fees
240' Private Beachfront @Kent Island Love Point - Great for Families
Kitchen
Kitchen
Kitchen
Kitchen
Exceptional
(32 reviews)

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

Stevensville

12% off
NZ$3,608
for 7 nights, 1 room
NZ$515 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Room
Living area
Interior
Interior
Exceptional
(16 reviews)

Waterfront 4 BR home with private pier and boat dock

Grasonville

8% off
NZ$9,825
for 7 nights, 1 home
NZ$1,404 per night
includes taxes & fees
Waterfront 4 BR home with private pier and boat dock
Big Internet TV above the table and another above dining room buffet downstairs.
In Stevensville MD 5 miles to Chesapeake Bay Bridge. 20 miles o Annapolis.
Inquire on both homes: togetherness without everyone being under the same roof!
Ready for some friendly competition? Enjoy our reversible tabletop shuffleboard.
Exceptional
(43 reviews)

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

8% off
NZ$10,278
for 7 nights, 1 home
NZ$1,468 per night
includes taxes & fees
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Interior
Living area
Private kitchen
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
Private kitchen
3 covered balconies, a patio, ceramic & propane grills, table seats 10-12 !
Dining
Master bedroom suite w/ private covered balcony
Exceptional
(79 reviews)

Charming Annapolis WaterVIEW Home

Annapolis

11% off
NZ$5,780
for 7 nights, 1 home
NZ$826 per night
includes taxes & fees
Charming Annapolis WaterVIEW Home
Interior
Pool
Property grounds
Private kitchen
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!
Private kitchen
Property grounds
Interior
Dining
Exceptional
(37 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
NZ$8,867
for 7 nights, 1 home
NZ$1,267 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
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).
Light and bright dining room with space for 6 (plus a high chair).
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Wonderful
(7 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
NZ$3,293
for 7 nights, 1 home
NZ$470 per night
includes taxes & fees
Cozy Cottage with Beach Access
Dining
Terrace/patio
Back yard and fire pit
Living area
Exceptional
(50 reviews)

Water Views - Close to Downtown Annapolis

Annapolis

5% off
NZ$6,762
for 7 nights, 1 home
NZ$966 per night
includes taxes & fees
Water Views - Close to Downtown Annapolis
Room
Dining
Interior
Living area
Exceptional
(16 reviews)

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

8% off
NZ$4,060
for 7 nights, 1 home
NZ$580 per night
includes taxes & fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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Explore the waterfront setting in Chester

The island views and other outdoor surroundings create an inviting atmosphere in Chester. Renowned for its boating, cycling and seafood restaurants, this city welcomes all visitors. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Chester

Are you hoping to discover top things to see and do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Chester a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Queenstown Harbor Golf (6.6 mi / 10.6 km)
  • Bay Hills Golf Club (11.3 mi / 18.1 km)
  • St. Michaels Winery (13.9 mi / 22.4 km)
  • Maryland Renaissance Festival (16.2 mi / 26 km)
  • Paul Reed Smith Guitars (1.6 mi / 2.6 km)
  • U.S. Naval Academy Golf Club (9.5 mi / 15.3 km)

Exploring the natural landscape of Chester

Whether you're an active traveller or just want to take in the scenery, Chester is a great spot to appreciate mother nature. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Northern Chesapeake Bay (3.1 mi / 5 km)
  • Eastern Neck National Wildlife Refuge (5.2 mi / 8.4 km)
  • Sandy Point Beach (6.2 mi / 10 km)
  • Bay Ridge Beach (9.2 mi / 14.8 km)
  • Maryland Quiet Waters Park (11.4 mi / 18.3 km)
  • Fort Smallwood Park (15.9 mi / 25.5 km)

Travelling to and around Chester

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 16.6 mi (26.7 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 24.8 mi (39.9 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a holiday rental?
When considering a holiday rental in Chester, Maryland, a popular area to stay in is along the waterfront, particularly near the Chester River. This picturesque location not only offers beautiful views but also provides easy access to a variety of recreational activities. The nearby Kent Island features charming shops, delightful eateries, and scenic parks, making it a fantastic spot for relaxation and exploration.For those who enjoy outdoor activities, the Chesapeake Bay Environmental Centre is a must-visit attraction. This centre offers trails and educational programs that highlight the region's natural beauty and wildlife. Additionally, the picturesque views from the Chesapeake Bay Bridge are worth experiencing, providing a great backdrop for memorable photographs.The waterfront area boasts a selection of properties that cater to various budgets, from cosy cottages to more spacious homes, ensuring that visitors can find something that fits their needs.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, holiday houses are the most popular type of holiday rental, with around 16 available in the area. These houses typically offer spacious living arrangements, often featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. The properties are generally situated in quiet neighbourhoods, making them ideal for families or groups seeking a comfortable retreat. Additionally, there are several apartments available, which provide a more compact lodging option, often equipped with essential amenities for a convenient stay.
Are there any family house rentals in Chester?
In Chester, Maryland, there are several family-friendly house rentals available that cater to various needs. Visitors can find homes in close proximity to the scenic Chester River, which offers opportunities for fishing, kayaking, and enjoying nature. Many of these properties feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces superb for children to play.The nearby community of Kent Island is also worth exploring, with its charming shops and restaurants. Families can take advantage of amenities such as Wi-Fi, air conditioning, and sometimes even access to private docks or outdoor grilling areas.
Are there any remote work holiday rentals in Chester?
In Chester, Maryland, there are several remote work-friendly holiday rentals available, with around 14 options to choose from. This charming area offers a peaceful setting for those looking to blend work and leisure. Many of the properties come equipped with essential amenities for remote work, including free Wi-Fi, dedicated desks, and comfortable chairs, allowing guests to create an effective workspace.The location is ideal for enjoying the picturesque surroundings, with easy access to nearby attractions such as the Chesapeake Bay and local parks. Travellers can expect well-furnished accommodations that provide a conducive environment for both productivity and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Chester?
In Chester, popular holiday rentals typically feature a range of amenities to enhance the stay for visitors. Most properties include well-equipped kitchens, allowing guests to prepare their own meals. Additionally, many rentals offer coffee and tea makers for a convenient morning routine. Outdoor spaces such as decks or patios are common, providing a pleasant area to relax and enjoy the surroundings. Onsite parking is also an essential amenity for those travelling by car. For those needing to work during their stay, many rentals include a desk, making it easier to maintain productivity while enjoying the charm of Chester.
What are the top attractions in Chester?
In Chester, Maryland, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. The Chesapeake Bay is a significant draw, offering opportunities for boating, fishing, and scenic waterfront walks. Nearby, the Kent Island Narrows provides stunning views and is a popular spot for dining and shopping.The historic district of Stevensville, just a short drive away, features quaint shops and local eateries, giving visitors a taste of the area's history and culture. Additionally, the Chesapeake Bay Environmental Centre offers educational programs and nature trails, making it an excellent destination for outdoor enthusiasts and families looking to explore the local ecosystem.For those interested in local arts and crafts, the nearby town of Easton hosts various galleries and events, enhancing the cultural experience for visitors.
Are all fees included in the Chester 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 Chester holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Chester 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 Chester holiday homes?
You can find great discounts on holiday homes in Chester 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 Chester holiday home booking on Bookabach?
To find Chester 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 Chester?
A long-stay holiday home in Chester 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 Chester holiday home?
Book your Chester 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 Chester?
Prices for holiday homes in Chester 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 Chester 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.