Photo by Patricia Knorr

Chester holiday rentals

We found 200 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:13 Nov - 20 Nov

Exterior
Kitchen
Kitchen
Kitchen
Exceptional
(28 reviews)

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

Stevensville

12% off
AU$3,006
for 7 nights, 1 room
AU$429 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Outdoor dining
Private kitchen
Room
Dining
Exceptional
(20 reviews)

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

Annapolis

16% off
AU$8,190
for 7 nights, 1 home
AU$1,170 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Beautiful waterfront home on Burley Creek with private pier
Enjoy screened in porch with dining table and sitting area
West-facing screened porch with bar area and café lights for night ambience
Sitting area overlooking Burley Creek
Exceptional
(60 reviews)

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

Annapolis

8% off
AU$7,334
for 7 nights, 1 home
AU$1,048 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
LARGE OPEN KITCHEN
SCREENED PORCH
PUBLIC BEACH/PARK 2 MILES AWAY
DINING ROOM SEATS 10-14 W/LEAFS
Exceptional
(44 reviews)

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

Annapolis

12% off
AU$8,472
for 7 nights, 1 home
AU$1,210 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Interior
Living area
Interior
Room
Exceptional
(14 reviews)

Waterfront 4 BR home with private pier and boat dock

Grasonville

8% off
AU$7,691
for 7 nights, 1 home
AU$1,099 per night
includes taxes & fees
Waterfront 4 BR home with private pier and boat dock
Living area
Pool
Exterior
Interior
Exceptional
(229 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,596
for 7 nights, 1 home
AU$657 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Living area
Pool
Exterior
Dining
Exceptional
(57 reviews)

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis

16% off
AU$4,749
for 7 nights, 1 home
AU$678 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
Interior
New Kitchen 2022
Exterior
Dining room
Exceptional
(64 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$5,241
for 7 nights, 1 home
AU$749 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Property grounds
Pool
Outdoor dining
Private kitchen
Exceptional
(214 reviews)

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

Stevensville

12% off
AU$4,615
for 7 nights, 1 room
AU$659 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Comfortable family room with reclining sofa, Smart TV and remote controlled window shades.
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.
Light and bright dining room with space for 6 (plus a high chair).
Exceptional
(7 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
AU$3,496
for 7 nights, 1 home
AU$499 per night
includes taxes & fees
Cozy Cottage with Beach Access
Private kitchen
Property grounds
Water view from the kitchen
Bathroom
Exceptional
(29 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
AU$6,915
for 7 nights, 1 home
AU$988 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Private kitchen
Terrace/patio
Back yard and fire pit
Dining
Exceptional
(47 reviews)

Water Views - Close to Downtown Annapolis

Annapolis

5% off
AU$5,294
for 7 nights, 1 home
AU$756 per night
includes taxes & fees
Water Views - Close to Downtown Annapolis
Exterior
Living area
Private kitchen
Dining
Exceptional
(49 reviews)

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

Stevensville

8% off
AU$9,132
for 7 nights, 1 home
AU$1,305 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
  • 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

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)
  • St. Michaels Winery (13.9 mi / 22.4 km)
  • Maryland Renaissance Festival (16.2 mi / 26 km)
  • U.S. Naval Academy Golf Club (9.5 mi / 15.3 km)
  • Bay Hills Golf Club (11.3 mi / 18.1 km)
  • Severna Park Golf Center (13.2 mi / 21.2 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)
  • Chesapeake Bay Environmental Center (3.8 mi / 6.1 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)
  • Eastern Neck National Wildlife Refuge (5.2 mi / 8.4 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 most popular type of holiday home accommodation in Chester?
The most in-demand types of holiday homes in Chester are houses. Prefer something different? Stayz has a variety of options to match the unique needs of our guests, so you'll see holiday homes in all sizes and shapes. The perfect home away from home is waiting for you — discover yours today.
How much does it cost to rent a holiday home in Chester?
Several factors affect how much you pay for a holiday home in Chester, such as the type of property, season and length of stay. But, all Stayz homes have one thing in common — unbeatable value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Chester?
The average price for a holiday home close to the beach in Chester depends on when you're travelling and the type and size of property you want. You can easily find prices on Stayz by entering your destination and preferred travel dates. Then make use of the filter tool to pick the number of bedrooms and amenities that you prefer, like a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Chester?
Pack up a suitcase for your puppy dog because Chester has five holiday homes that throw out the welcome mat to pets. Let your furriest pal get in on the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Chester?
Pack your swimming gear and inflatable flamingo, because there are two houses with a private pool in Chester. Stay at one of these superb holiday homes and enjoy a pool day every day. Simply enter your dates into Stayz, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Chester?
The most popular home amenities people look for in Chester include a garden, nearby museums and a fireplace. Whether you're on a trip with family, pals or even pets, Stayz holiday homes provide the best amenities for chilling out with the people who matter most.
Are there large group holiday homes in Chester?
Choose from two holiday homes in Chester that can host 10 or more guests. Whether you're organising a family trip or a celebration like an anniversary, there's plenty of room to get your loved ones together under one roof.
Are there holiday homes in Chester that welcome kids?
Chester has five family-friendly holiday homes to pick from. And finding a stay that welcomes kids is a cinch with Stayz's "Properties good for families" filter. In addition to having the entire place to yourselves, you'll have access to conveniences and perks like extra bedrooms, kitchens and yards.
What are the top attractions for families in Chester?
Keeping the kids entertained during your stay in Chester is simple with these cool family-friendly attractions:
  • Sandy Point Beach
  • Bay Ridge Beach
  • Sandy Point State Park
Are there holiday homes with WiFi in Chester?
Take your pick of two holiday homes with WiFi in Chester. If you'd like to disconnect from the world while on holiday, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Chester?
Chester has four holiday homes where you'll be able to kick back in air-conditioned comfort. To find a stay on Stayz that features this perk, enter your preferred travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Chester?
The minimum age is generally 16, 18 or 21. It can vary between properties on Stayz, so look at the rules of your chosen Chester stay before booking your stay.
How long can I rent a holiday home in Chester for?
How long you can rent a holiday home in Chester depends on the property. Simply enter your chosen travel dates to see a list of options offering extended stays. With loads of creature comforts such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to find a perfect place to call your home away from home in Chester.