A coastal town with a marina, a bridge, and a highway.

Search Holiday Homes in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chester holiday homes

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (49 reviews)
"Great stay"
United States
Michael V.
The price is £242
includes taxes & fees
2 Nov - 3 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

2. 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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is £226
includes taxes & fees
1 Nov - 2 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A bedroom with a bed, a desk, a chair, a ceiling fan, a TV, and a window.

3. 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, (43 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is £250
includes taxes & fees
2 Nov - 3 Nov
Large 2 bedroom house with private parking in a nice neighborhood
A hot tub with a white deck and railing, surrounded by trees and a house in the background.

4. 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, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is £368
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A building with a gabled roof and a circular vent on the roof.

5. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is £239
includes taxes & fees
27 Oct - 28 Oct
BAYSIDE BUNGALOW
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

6. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is £406
includes taxes & fees
27 Oct - 28 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (28 reviews)
"Lovely place to stay. Very nice area and the host was very accommodating."
United States
Jax H.
The price is £161
includes taxes & fees
1 Nov - 2 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

8. 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 £429
includes taxes & fees
10 Nov - 11 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
Three birds perched on a wooden structure by the water.

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

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is £977
includes taxes & fees
27 Oct - 28 Oct
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

10. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is £432
includes taxes & fees
27 Oct - 28 Oct
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A spacious living room with a large sofa, a coffee table, and a chandelier. There is a kitchen in the background with a dining area.

11. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (10 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is £402
includes taxes & fees
2 Nov - 3 Nov
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

12. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is £919
includes taxes & fees
27 Oct - 28 Oct
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A modern kitchen with a central island, built-in oven, and microwave.

13. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
The price is £376
includes taxes & fees
27 Oct - 28 Oct
Cute bungalow blocks to Stadium
A two-story house with a red roof, a brick chimney, and a small porch.

14. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.4 out of 10, Very good, (6 reviews)
"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...
United States
Michele F.
The price is £781
includes taxes & fees
27 Oct - 28 Oct
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A waterfront walkway with a brick path, a lamp post, and a bench.

15. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is £361
includes taxes & fees
2 Nov - 3 Nov
Cozy 2br home w/ parking in downtown Annapolis
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

16. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.4 out of 10, Exceptional, (3 reviews)
"Great little house on a perfect location"
United States
Amy T.
The price is £410
includes taxes & fees
27 Oct - 28 Oct
Historic Row Home in Downtown Annapolis
A dining area with a wooden table, chairs, a chandelier, and a clock on the wall.

17. Annapolis Charmer - Perfect Location

Annapolis Charmer - Perfect Location
Historic District
The price is £462
includes taxes & fees
2 Nov - 3 Nov
Annapolis Charmer - Perfect Location
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

18. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is £457
includes taxes & fees
3 Nov - 4 Nov
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

19. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is £525
includes taxes & fees
27 Oct - 28 Oct
Family Home on Mayo Peninsula | Deck | Sleeps 10
A spacious living room with a high ceiling, large windows, and a ceiling fan.

20. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is £320
includes taxes & fees
27 Oct - 28 Oct
The Harness Creek Retreat in Annapolis
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great location, friendly staff."
Joel 3-night trip
Posted 6 hours ago
Hilton Garden Inn Annapolis Downtown

Find out more about Chester

Chester Holiday Homes information

Number of reviews
469
Accommodation
610 Holiday Homes
Lowest Price
£161
Highest Price
£977