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Vacation Homes in Chester

Sunset Cottage - West River Access and Views!

2.0 star property
Shady Side
$469 nightly
The price is $476
Nov 11 - Nov 12
Total with taxes and fees
Sunset Cottage - West River Access and Views!

Historic Downtown Luxury • USNA • Waterfront

Historic District
$563 nightly
The price is $573
Nov 11 - Nov 12
Total with taxes and fees
Historic Downtown Luxury • USNA • Waterfront

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

Stevensville
9.6 out of 10, Exceptional, (31)
"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
$234 nightly
The price is $248
Nov 12 - Nov 13
Total with taxes and fees
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Centreville
10.0 out of 10, Exceptional, (7)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
$420 nightly
The price is $445
Nov 17 - Nov 18
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
$248 nightly
The price is $263
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

Grasonville
9.6 out of 10, Exceptional, (12)
"I was impressed with how spacious and clean the house was."
United States
Susan M.
$395 nightly
The price is $419
Nov 11 - Nov 12
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (1)
"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.
$257 nightly
The price is $272
Nov 11 - Nov 12
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants

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.
$320 nightly
The price is $353
Dec 1 - Dec 2
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes

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.
$399 nightly
The price is $454
Nov 17 - Nov 18
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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.
$378 nightly
The price is $417
Nov 11 - Nov 12
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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

Shady Side
10.0 out of 10, Exceptional, (4)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
$376 nightly
The price is $429
Nov 11 - Nov 12
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
9.4 out of 10, Exceptional, (31)
"This was a great place to stay with everything you needed. I loved the furniture in the house and it was well decorated, not to mention the neighborhood was quiet and close to all these good restaurants. Parking was a breeze for us since we drove in two cars. We parked in the wrap around driveway. There is a small fenced in back yard so it was perfect to let the dog run around and do his business. The host was great and couldn’t have asked for a better stay. "
United States
Mateusz K.
$268 nightly
The price is $306
Nov 11 - Nov 12
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

Neptune by the Water - Pet Friendly Fenced Yard

Cape Saint Claire
9.8 out of 10, Exceptional, (11)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
$468 nightly
The price is $497
Nov 11 - Nov 12
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (24)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
United States
Mireia A.
$480 nightly
The price is $510
Nov 11 - Nov 12
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere
10.0 out of 10, Exceptional, (4)
"Property was perfect for my regatta crew. Loved it."
United States
Michael Q.
$482 nightly
The price is $549
Nov 11 - Nov 12
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie
8.4 out of 10, Very Good, (7)
"We were in town for a family wedding and needed a peaceful "home base" to relax and get ready. "The Hideaway Spot" was absolutely perfect! It is an upscale nautical cabin-like interior with plenty of room for 2 couples. The outside deck was great for coffee and chilling together. Peaceful getaway from hustle and bustle of the city. Plenty of fabulous seafood in Glen Burnie nearby. Communication with host was easy with prompt responses and attention to any requests/questions we had. The family...
United States
Ashlee H.
$305 nightly
The price is $348
Nov 11 - Nov 12
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Modern New Suite Close to US Capital and BWI Airport

Pasadena
7.0 out of 10, Good, (2)
"Great location but horrible noise level AT the property as well as someone else’s hair in the carpets in our room. The property manager communicated well, however, we shouldn’t have had to ask on more than one occasion for his tenant to stop playing his game so loudly at night. We also shouldn’t have had someone else hair in our room and on our belongings. Would not stay again. "
United States
Lenny J.
$129 nightly
The price is $147
Dec 6 - Dec 7
Total with taxes and fees
Modern New Suite Close to US Capital and BWI Airport

Holly Hill Haven - Sleeps 10

Edgewater
10.0 out of 10, Exceptional, (3)
"Only thing is I would better stock the kitchen. Other than that NO COMPLAINTS! Great location, great clean and comfortable home to host thanksgiving "
United States
Brittany B.
$466 nightly
The price is $496
Nov 17 - Nov 18
Total with taxes and fees
Holly Hill Haven - Sleeps 10

Cute bungalow blocks to Stadium

Admiral Heights
10.0 out of 10, Exceptional, (5)
"We had a great stay in this property. The inside looks just like the pictures and feels like it was newly renovated. The kitchen and baths were spectacular. The location was great, it is less than 1/4 mile to the USNA Marine Corps Stadium and also has great access to West Street and all that has to offer. It's a nice quiet neighborhood, jogging trail right in front of the house, close to shopping and dining. The beds and linens were fresh and comfortable. The open floor plan layout...
United States
Tim G.
$473 nightly
The price is $535
Nov 11 - Nov 12
Total with taxes and fees
Cute bungalow blocks to Stadium

Cozy 2br home w/ parking in downtown Annapolis

Historic District
10.0 out of 10, Exceptional, (71)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$269 nightly
The price is $307
Nov 17 - Nov 18
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
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
300
Accommodation
688 Vacation Homes
Lowest Price
$147
Highest Price
$549

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