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Our top choices for Chester vacation homes

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (33 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AED 258
AED 927 total
includes taxes & fees
24 Feb - 25 Feb
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 AED 234
AED 898 total
includes taxes & fees
24 Feb - 25 Feb
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 AED 918
AED 1,546 total
includes taxes & fees
24 Feb - 25 Feb
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 AED 633
AED 1,781 total
includes taxes & fees
24 Feb - 25 Feb
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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 AED 300
AED 1,188 total
includes taxes & fees
1 Mar - 2 Mar
Walk to Beach! King Bed & Free Beach Passes

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 AED 463
AED 1,164 total
includes taxes & fees
1 Mar - 2 Mar
Large 2 bedroom house with private parking in a nice neighborhood

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 AED 551
AED 2,073 total
includes taxes & fees
24 Feb - 25 Feb
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 AED 826
AED 1,914 total
includes taxes & fees
2 Mar - 3 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 AED 569
AED 1,628 total
includes taxes & fees
1 Mar - 2 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
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 AED 628
AED 2,044 total
includes taxes & fees
24 Feb - 25 Feb
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 AED 607
AED 1,312 total
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging

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 AED 282
AED 820 total
includes taxes & fees
24 Feb - 25 Feb
Cute, Cozy 2-bedroom house in near Annapolis with water access

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is AED 551
AED 1,454 total
includes taxes & fees
24 Feb - 25 Feb
Sunset Cottage - West River Access and Views!

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 AED 584
AED 1,909 total
includes taxes & fees
12 Mar - 13 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!

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 AED 485
AED 2,588 total
includes taxes & fees
24 Feb - 25 Feb
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is AED 735
AED 1,390 total
includes taxes & fees
24 Feb - 25 Feb
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

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 AED 541
AED 1,471 total
includes taxes & fees
26 Mar - 27 Mar
The Hideaway Spot- Waterfront w/ Dock on Long Cove

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 AED 621
AED 1,386 total
includes taxes & fees
15 Mar - 16 Mar
Cozy 2br home w/ parking in downtown Annapolis

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (7 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 AED 918
AED 1,436 total
includes taxes & fees
25 Feb - 26 Feb
Walk to the stadium! - Lighthouse on Glenwood
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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