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28 Nov - 30 Nov
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5 Dec - 7 Dec
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19 Dec - 21 Dec
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16 Jan - 18 Jan

Vacation Homes in Chester

Marina
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, (42)
"Wonderful home and host. Very easy to check-in and communication was excellent. "
United States
Ann T.
The price is SAR 295
SAR 977 total
includes taxes & fees
25 Nov - 26 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is SAR 232
SAR 902 total
includes taxes & fees
23 Nov - 24 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"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 SAR 288
SAR 1,144 total
includes taxes & fees
23 Nov - 24 Nov
Walk to Beach! King Bed & Free Beach Passes
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is SAR 739
SAR 1,670 total
includes taxes & fees
2 Dec - 3 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Exterior
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)
"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 SAR 938
SAR 1,570 total
includes taxes & fees
24 Nov - 25 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Fridge, microwave, oven, stovetop
Modern New Suite Close to US Capital and BWI Airport

Modern New Suite Close to US Capital and BWI Airport

Pasadena
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
United States
Brittnie A.
The price is SAR 263
SAR 552 total
includes taxes & fees
6 Dec - 7 Dec
Modern New Suite Close to US Capital and BWI Airport
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
The price is SAR 813
SAR 2,022 total
includes taxes & fees
23 Nov - 24 Nov
Charming Pet-Friendly Stay - Near Bay & Beaches.
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is SAR 844
SAR 1,022 total
includes taxes & fees
23 Nov - 24 Nov
Chesapeake Bay Harbor View in a central location to events/restaurants
Beach nearby, sun loungers, beach towels
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, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is SAR 482
SAR 1,667 total
includes taxes & fees
23 Nov - 24 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop
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)
"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 SAR 780
SAR 2,181 total
includes taxes & fees
9 Dec - 10 Dec
Neptune by the Water - Pet Friendly Fenced Yard
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is SAR 675
SAR 1,034 total
includes taxes & fees
23 Nov - 24 Nov
BAYSIDE BUNGALOW
TV, books, offices
Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10

Edgewater
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is SAR 555
SAR 1,873 total
includes taxes & fees
9 Dec - 10 Dec
Holly Hill Haven - Sleeps 10
Exterior
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)
"Would stay here again "
United States
Thomas D.
The price is SAR 540
SAR 1,608 total
includes taxes & fees
23 Nov - 24 Nov
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Marina
Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Rock Hall
10.0 out of 10, Exceptional, (2)
"I spent a wonderful 8 nights at the Dragonfly Cottage in the quaint bayside town of Rock Hall. The cottage was in a prime location and perfectly situated for long morning walks around the town. The cottage itself is brand new with every accommodation you can think of to have a comfortable stay. The 3 large bedrooms and open floor plan kitchen / living area provide plenty of space to spread out. Everything was sparkling clean and you can tell the hosts have taken a lot of care to anticipate your...
United States
Alison F.
Sparkling new! A Craftsman-style cottage in the heart of Rock Hall
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (24)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is SAR 848
SAR 2,316 total
includes taxes & fees
9 Dec - 10 Dec
Edgewater/Mayo Gateaway w/ Hot Tub
Smart TV, books
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, (33)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is SAR 489
SAR 1,216 total
includes taxes & fees
23 Nov - 24 Nov
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie
8.4 out of 10, Very Good, (7)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is SAR 408
SAR 1,304 total
includes taxes & fees
2 Dec - 3 Dec
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Microwave, oven, stovetop, dishwasher
Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere
10.0 out of 10, Exceptional, (4)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is SAR 638
SAR 2,005 total
includes taxes & fees
9 Dec - 10 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!
Property grounds
Cozy Private Suite in Eastport, Near USNA

Cozy Private Suite in Eastport, Near USNA

Eastport
The price is SAR 233
SAR 599 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Private Suite in Eastport, Near USNA
Terrace/patio
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)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is SAR 861
SAR 1,977 total
includes taxes & fees
30 Nov - 1 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community 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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Check in was easy! Staff very friendly and helpful."
Ned 1-night trip
Posted 2 days ago
Hilton Garden Inn Kent Island Marina