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

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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 vacation homes

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is AED 333
AED 1,016 total
includes taxes & fees
2 Nov - 3 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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 AED 259
AED 977 total
includes taxes & fees
1 Nov - 2 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A building with a gabled roof and a circular vent on the roof.

3. 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 AED 735
AED 1,159 total
includes taxes & fees
31 Oct - 1 Nov
BAYSIDE BUNGALOW
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

4. 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 AED 496
AED 1,223 total
includes taxes & fees
2 Nov - 3 Nov
Large 2 bedroom house with private parking in a nice neighborhood
A beach with chairs and a pier in the background.

5. 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 AED 711
AED 1,765 total
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

6. 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 AED 2,935
AED 5,092 total
includes taxes & fees
2 Nov - 3 Nov
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

7. 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 AED 771
AED 2,152 total
includes taxes & fees
16 Nov - 17 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
Three birds perched on a wooden structure by the water.

8. 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 AED 2,935
AED 5,092 total
includes taxes & fees
1 Nov - 2 Nov
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

9. 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, (30 reviews)
"Lovely place to stay. Very nice area and the host was very accommodating."
United States
Jax H.
The price is AED 245
AED 773 total
includes taxes & fees
1 Nov - 2 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access
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 AED 1,074
AED 2,129 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 808
AED 2,131 total
includes taxes & fees
2 Nov - 3 Nov
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
A modern kitchen with a central island, built-in oven, and microwave.

12. 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.
Cute bungalow blocks to Stadium
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 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 AED 707
AED 2,038 total
includes taxes & fees
31 Oct - 1 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

14. 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 AED 771
AED 2,573 total
includes taxes & fees
2 Nov - 3 Nov
Historic Row Home in Downtown Annapolis
A wooden dock extending into a calm body of water with boats docked at the end.

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 AED 1,065
AED 1,951 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 2br home w/ parking in downtown Annapolis
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

16. Mins to Historic Downtown Annapolis - Parking

Mins to Historic Downtown Annapolis - Parking
Annapolis
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful home with very attentive host. Great place for family getaway. Will definitely be back! Go Navy."
United States
Nader E.
The price is AED 853
AED 1,935 total
includes taxes & fees
9 Nov - 10 Nov
Mins to Historic Downtown Annapolis - Parking
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

17. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Good location."
United States
Rosie G.
The price is AED 799
AED 2,898 total
includes taxes & fees
2 Nov - 3 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.

18. 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 AED 889
AED 2,601 total
includes taxes & fees
31 Oct - 1 Nov
Family Home on Mayo Peninsula | Deck | Sleeps 10
A spacious living room with a high ceiling, large windows, and a ceiling fan.

19. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is AED 992
AED 1,570 total
includes taxes & fees
2 Nov - 3 Nov
The Harness Creek Retreat in Annapolis
Interior

20. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Great property!"
United States
Michael Z.
The price is AED 797
AED 2,569 total
includes taxes & fees
3 Nov - 4 Nov
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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.
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Top Chester Hotel Reviews

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"I enjoyed my stay for two nights, My room was clean and comfortable and I loved the water pressure in my shower! The view of the water is so pretty and the staff is amazing😊 I especially want to recognize the sweet lady at the front desk! I believe her name is Charlene. She is so kind and extremely helpful!! I definitely will stay here again,when I come to visit my sister in Queenstown. Thank you for everything 😊"
Jean (Jeannie) 2-night trip
Posted 15 hours ago
Hyatt Place Kent Narrows & Marina