Chester Vacation Rentals

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Our top choices for Chester vacation homes

9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is CA $342
CA $577 total
includes taxes & fees
Mar 12 - Mar 13
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is CA $127
CA $382 total
includes taxes & fees
Mar 8 - Mar 9
Charming Coastal/Country Home w/3 Acres & Sauna!
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is CA $127
CA $382 total
includes taxes & fees
Mar 10 - Mar 11
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is CA $172
CA $436 total
includes taxes & fees
Mar 10 - Mar 11
Large 2 bedroom house with private parking in a nice neighborhood
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $236
CA $660 total
includes taxes & fees
Mar 8 - Mar 9
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is CA $112
CA $446 total
includes taxes & fees
Mar 9 - Mar 10
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is CA $257
CA $516 total
includes taxes & fees
Apr 1 - Apr 2
Bayside Cottage steps from Rock Hall Harbor

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is CA $193
CA $699 total
includes taxes & fees
Mar 5 - Mar 6
Cute bungalow blocks to Stadium

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is CA $205
CA $764 total
includes taxes & fees
Mar 5 - Mar 6
Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is CA $326
CA $733 total
includes taxes & fees
Mar 17 - Mar 18
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is CA $235
CA $500 total
includes taxes & fees
Mar 9 - Mar 10
Wright's Cottage- Pet's Welcome & EV Charging

Vacation Home in Historic District

Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (5 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 $193
CA $967 total
includes taxes & fees
Mar 5 - Mar 6
Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is CA $158
CA $590 total
includes taxes & fees
Mar 15 - Mar 16
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is CA $213
CA $604 total
includes taxes & fees
Mar 8 - Mar 9
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is CA $183
CA $451 total
includes taxes & fees
Mar 24 - Mar 25
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (1 review)
"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 CA $104
CA $302 total
includes taxes & fees
Mar 16 - Mar 17
Cute, Cozy 2-bedroom house in near Annapolis with water access
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is CA $217
CA $708 total
includes taxes & fees
Mar 12 - Mar 13
Annapolis Retreat - 7 mins from downtown Annapolis!
8.8 out of 10, Excellent, (9 reviews)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
United States
Jeffrey S.
The price is CA $177
CA $517 total
includes taxes & fees
Mar 9 - Mar 10
The Hideaway Spot- Waterfront w/ Dock on Long Cove
9.8 out of 10, Exceptional, (8 reviews)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
The price is CA $342
CA $532 total
includes taxes & fees
Mar 8 - Mar 9
Walk to the stadium! - Lighthouse on Glenwood
The price is CA $252
CA $593 total
includes taxes & fees
Mar 16 - Mar 17
Sunset Cottage - West River Access and Views!
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

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Chester Vacation Homes information

Number of reviews
287
Accommodation
659 Vacation Homes
Lowest Price
CA $302
Highest Price
CA $967

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