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Our top choices for Chester vacation homes

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 ¥10,930
¥38,817 total
includes taxes & fees
Jan 28 - Jan 29
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is ¥12,612
¥40,601 total
includes taxes & fees
Jan 29 - Jan 30
Charming Coastal/Country Home w/3 Acres & Sauna!
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 ¥38,925
¥65,357 total
includes taxes & fees
Jan 27 - Jan 28
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ¥31,140
¥46,707 total
includes taxes & fees
Jan 27 - Jan 28
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (18 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 ¥10,447
¥47,972 total
includes taxes & fees
Jan 27 - Jan 28
Walk to Beach! King Bed & Free Beach Passes
9.4 out of 10, Exceptional, (36 reviews)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is ¥18,217
¥47,570 total
includes taxes & fees
Jan 27 - Jan 28
Large 2 bedroom house with private parking in a nice neighborhood
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ¥18,155
¥67,314 total
includes taxes & fees
Jan 27 - Jan 28
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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 ¥26,833
¥75,497 total
includes taxes & fees
Jan 27 - Jan 28
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
The price is ¥12,705
¥35,962 total
includes taxes & fees
Feb 7 - Feb 8
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 ¥24,756
¥80,761 total
includes taxes & fees
Jan 27 - Jan 28
Annapolis Retreat - 7 mins from downtown Annapolis!
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 ¥32,230
¥77,034 total
includes taxes & fees
Feb 3 - Feb 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is ¥23,962
¥68,850 total
includes taxes & fees
Feb 1 - Feb 2
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
8.6 out of 10, Excellent, (8 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 ¥16,956
¥54,473 total
includes taxes & fees
Jan 27 - Jan 28
The Hideaway Spot- Waterfront w/ Dock on Long Cove
9.8 out of 10, Exceptional, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is ¥27,886
¥71,551 total
includes taxes & fees
Jan 27 - Jan 28
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
8.6 out of 10, Excellent, (10 reviews)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
The price is ¥13,873
¥19,366 total
includes taxes & fees
Jan 27 - Jan 28
Secluded Tiny Pool House -Private Pool -Self Check in

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (74 reviews)
"Great location!"
United States
Burton S.
The price is ¥25,691
¥57,687 total
includes taxes & fees
Feb 2 - Feb 3
Cozy 2br home w/ parking in downtown Annapolis
The price is ¥25,846
¥62,529 total
includes taxes & fees
Jan 28 - Jan 29
Sunset Cottage - West River Access and Views!

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is ¥22,732
¥81,154 total
includes taxes & fees
Jan 27 - Jan 28
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)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is ¥25,535
¥90,347 total
includes taxes & fees
Jan 28 - Jan 29
Neptune by the Water - Pet Friendly Fenced Yard
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is ¥23,822
¥76,324 total
includes taxes & fees
Feb 24 - Feb 25
London Towne Bungalow w/Loft - Walk to the Beach!
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

Find out more about Chester

Chester Vacation Homes information

Number of reviews
360
Accommodation
659 Vacation Homes
Lowest Price
¥19,366
Highest Price
¥90,347