A boat docked at a pier during twilight with a city skyline in the background.

Chester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chester vacation rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (114 reviews)
"Every thing was great"
United States
lesia k.
The price is ¥16,012
¥25,691 total
includes taxes & fees
Jun 30 - Jul 1
First Floor Studio Apartment in Historic Chestertown

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is ¥23,800
¥57,279 total
includes taxes & fees
Jul 1 - Jul 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (23 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ¥19,053
¥46,212 total
includes taxes & fees
Jun 29 - Jun 30
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is ¥17,453
¥48,347 total
includes taxes & fees
Jun 30 - Jul 1
Charming Coastal/Country Home w/3 Acres & Sauna!

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (29 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ¥40,435
¥62,301 total
includes taxes & fees
Jun 29 - Jun 30
Newly restored apartment in the heart of Chestertown

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (56 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ¥32,348
¥48,347 total
includes taxes & fees
Jun 29 - Jun 30
BAYSIDE BUNGALOW

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is ¥27,658
¥61,400 total
includes taxes & fees
Jul 1 - Jul 2
Large 2 bedroom house with private parking in a nice neighborhood

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ¥33,965
¥65,663 total
includes taxes & fees
Jul 14 - Jul 15
Bayside Cottage steps from Rock Hall Harbor

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is ¥26,663
¥70,223 total
includes taxes & fees
Jun 30 - Jul 1
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.6 out of 10, Exceptional, (10 reviews)
"Great place!"
United States
Chris A.
The price is ¥21,228
¥56,652 total
includes taxes & fees
Jun 30 - Jul 1
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is ¥18,196
¥49,507 total
includes taxes & fees
Jun 30 - Jul 1
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (11 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is ¥13,829
¥37,707 total
includes taxes & fees
Jun 29 - Jun 30
Cute, Cozy 2-bedroom house near Annapolis with water access

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is ¥25,387
¥67,509 total
includes taxes & fees
Jul 15 - Jul 16
Walk to Beach! King Bed & Free Beach Passes

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (84 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ¥46,096
¥83,341 total
includes taxes & fees
Jul 14 - Jul 15
Waterfront Oasis of Annapolis Star

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home for a girls weekend away. The view is spectacular, host was communicative, and lots of thoughtful small touches throughout the home and the experience. Thank you for a wonderful stay! "
United States
Katie K.
The price is ¥51,919
¥96,110 total
includes taxes & fees
Jul 6 - Jul 7
Sunset Cottage - West River Access and Views!

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (8 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is ¥31,216
¥90,533 total
includes taxes & fees
Jun 29 - Jun 30
Renovated Bungalow | Walk to Beach | Dog-Friendly

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is ¥58,226
¥107,495 total
includes taxes & fees
Jun 29 - Jun 30
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (15 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is ¥63,321
¥119,388 total
includes taxes & fees
Jul 6 - Jul 7
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ¥40,435
¥101,964 total
includes taxes & fees
Jul 20 - Jul 21
Annapolis Retreat - 7 mins from downtown Annapolis!

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is ¥39,141
¥112,105 total
includes taxes & fees
Jun 29 - Jun 30
Family Home on Mayo Peninsula | Deck | Sleeps 10
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near well known sights in Chester, or you can go with a secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and seafood restaurants. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best vacation rentals that Chester has to offer?

Charming Annapolis WaterVIEW Home: This vacation home rental near Chester is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals will I find in Chester?

Choose from 8 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Northern Chesapeake Bay. Matapeake State Park and Chesapeake Bay Environmental Center are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.