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Our top choices for Chester holiday homes

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
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 HK$1,951
HK$3,284 total
includes taxes & fees
18 Mar - 19 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is HK$672
HK$2,102 total
includes taxes & fees
8 Mar - 9 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!

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, (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 HK$672
HK$2,094 total
includes taxes & fees
10 Mar - 11 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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, (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 HK$983
HK$2,474 total
includes taxes & fees
8 Mar - 9 Mar
Large 2 bedroom house with private parking in a nice neighborhood

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
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 HK$639
HK$2,527 total
includes taxes & fees
9 Mar - 10 Mar
Walk to Beach! King Bed & Free Beach Passes

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
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 HK$1,345
HK$3,785 total
includes taxes & fees
8 Mar - 9 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
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 HK$1,467
HK$2,904 total
includes taxes & fees
1 Apr - 2 Apr
Bayside Cottage steps from Rock Hall Harbor

Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard
Cape Saint Claire
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 HK$1,171
HK$4,280 total
includes taxes & fees
9 Mar - 10 Mar
Neptune by the Water - Pet Friendly Fenced Yard

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
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$1,864
HK$4,211 total
includes taxes & fees
17 Mar - 18 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
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 HK$1,102
HK$4,039 total
includes taxes & fees
8 Mar - 9 Mar
Cute bungalow blocks to Stadium

Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging
Annapolis
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is HK$1,338
HK$2,860 total
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is HK$1,215
HK$3,467 total
includes taxes & fees
8 Mar - 9 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
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 HK$903
HK$3,346 total
includes taxes & fees
15 Mar - 16 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is HK$1,040
HK$2,567 total
includes taxes & fees
24 Mar - 25 Mar
Cozy 2br home w/ parking in downtown Annapolis

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

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
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 HK$593
HK$1,699 total
includes taxes & fees
16 Mar - 17 Mar
Cute, Cozy 2-bedroom house in near Annapolis with water access

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
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 HK$1,241
HK$4,057 total
includes taxes & fees
16 Mar - 17 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
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 HK$977
HK$2,885 total
includes taxes & fees
22 Mar - 23 Mar
The Hideaway Spot- Waterfront w/ Dock on Long Cove

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
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 HK$1,413
HK$5,997 total
includes taxes & fees
18 Mar - 19 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
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 HK$1,951
HK$3,052 total
includes taxes & fees
8 Mar - 9 Mar
Walk to the stadium! - Lighthouse on Glenwood

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is HK$1,321
HK$3,261 total
includes taxes & fees
11 Mar - 12 Mar
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

Find out more about Chester

Chester Vacation Homes information

Number of reviews
287
Accommodation
659 Vacation Homes
Lowest Price
HK$1,699
Highest Price
HK$5,997

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