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

Chester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (47 reviews)
"Great stay"
United States
Michael V.
The price is CA $100
CA $378 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $100
CA $378 total
includes taxes & fees
Oct 19 - Oct 20
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

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 CA $197
CA $473 total
includes taxes & fees
Oct 20 - Oct 21
Large 2 bedroom house with private parking in a nice neighborhood
A building with a gabled roof and a circular vent on the roof.

4. 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 CA $283
CA $446 total
includes taxes & fees
Oct 20 - Oct 21
BAYSIDE BUNGALOW
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

5. 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)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
The price is CA $93
CA $295 total
includes taxes & fees
Oct 19 - Oct 20
Cute, Cozy 2-bedroom house near Annapolis with water access
A wooden dock extending into a calm body of water with boats docked at the end.

6. 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 CA $354
CA $675 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 2br home w/ parking in downtown Annapolis
Three birds perched on a wooden structure by the water.

7. 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 CA $1,061
CA $1,868 total
includes taxes & fees
Oct 19 - Oct 20
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A beach with chairs and a pier in the background.

8. 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)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $311
CA $725 total
includes taxes & fees
Nov 3 - Nov 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

9. 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 CA $296
CA $824 total
includes taxes & fees
Nov 3 - Nov 4
Annapolis Retreat - 7 mins from downtown Annapolis!
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 CA $414
CA $825 total
includes taxes & fees
Oct 19 - Oct 20
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

11. 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, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is CA $990
CA $1,780 total
includes taxes & fees
Oct 19 - Oct 20
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
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.
The price is CA $280
CA $738 total
includes taxes & fees
Oct 19 - Oct 20
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
9.8 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 CA $272
CA $796 total
includes taxes & fees
Oct 19 - Oct 20
Renovated Bungalow | Walk to Beach | Dog-Friendly
Interior

14. 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)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is CA $272
CA $803 total
includes taxes & fees
Oct 19 - Oct 20
Historic Row Home | Hot Tub - 1 Block from Gate 1!
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

15. 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 CA $263
CA $803 total
includes taxes & fees
Oct 19 - Oct 20
Historic Row Home in Downtown Annapolis
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

16. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Great property, great location. Host was super responsive and accommodating! Highly recommended."
United States
Remy S.
The price is CA $280
CA $1,751 total
includes taxes & fees
Oct 20 - Oct 21
Luxe Row Home Steps to USNA Gate 3!
A two-story house with a red roof, a brick chimney, and a small porch.

17. 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 CA $1,018
CA $1,490 total
includes taxes & fees
Oct 20 - Oct 21
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

18. Mins to DTA - King Beds - Parking

Mins to DTA - King Beds - Parking
Annapolis
10.0 out of 10, Exceptional, (5 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 CA $342
CA $769 total
includes taxes & fees
Nov 9 - Nov 10
Mins to DTA - King Beds - Parking
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 CA $373
CA $1,041 total
includes taxes & fees
Oct 21 - Oct 22
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 CA $382
CA $608 total
includes taxes & fees
Oct 19 - Oct 20
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Great location. Very clean."
scott 2-night trip
Posted 1 hour ago
St Michaels Inn

Find out more about Chester

Chester Vacation Homes information

Number of reviews
477
Accommodation
611 Vacation Homes
Lowest Price
CA $295
Highest Price
CA $1,868

Explore a world of travel with Expedia