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Vacation Homes in Chester

Our top choices for Chester vacation homes

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is AED 393
AED 1,181 total
includes taxes & fees
9 Sep - 10 Sep
Waterfront Getaway, Dock Your Boat & Play!

Waterfront House: Hot Tub, Fire Pit, & Views

9.4 out of 10, Exceptional, (3)
"Our stay was great! The convenience to nearby restaurants and stores worked really well for oir quick weekend trip! "
Waterfront House: Hot Tub, Fire Pit, & Views

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AED 521
AED 1,249 total
includes taxes & fees
1 Oct - 2 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is AED 724
AED 1,608 total
includes taxes & fees
8 Sep - 9 Sep
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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

9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
The price is AED 382
AED 1,113 total
includes taxes & fees
8 Sep - 9 Sep
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

10.0 out of 10, Exceptional, (30)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Modern New Suite Close to US Capital and BWI Airport

10.0 out of 10, Exceptional, (1)
"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! "
The price is AED 275
AED 561 total
includes taxes & fees
4 Sep - 5 Sep
Modern New Suite Close to US Capital and BWI Airport

Walk to Beach! King Bed & Free Beach Passes

10.0 out of 10, Exceptional, (16)
"Excellent"
Walk to Beach! King Bed & Free Beach Passes

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

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is AED 918
AED 1,515 total
includes taxes & fees
4 Sep - 5 Sep
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is AED 459
AED 1,696 total
includes taxes & fees
8 Sep - 9 Sep
Holly Hill Haven - Sleeps 10

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"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!"
The price is AED 962
AED 1,701 total
includes taxes & fees
16 Sep - 17 Sep
Bayside Cottage steps from Rock Hall Harbor

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AED 808
AED 1,763 total
includes taxes & fees
1 Oct - 2 Oct
The Cottage

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is AED 708
AED 1,879 total
includes taxes & fees
8 Sep - 9 Sep
Charming Pet-Friendly Stay - Near Bay & Beaches.

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

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Neptune by the Water - Pet Friendly Fenced Yard

9.6 out of 10, Exceptional, (10)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is AED 551
AED 1,831 total
includes taxes & fees
4 Sep - 5 Sep
Neptune by the Water - Pet Friendly Fenced Yard

Historic 3 BR Home - 15 Min Walk to N-MC Stadium

The price is AED 430
AED 2,223 total
includes taxes & fees
8 Sep - 9 Sep
Historic 3 BR Home - 15 Min Walk to N-MC Stadium

Fisher House: Steps From USNA + Covered Parking!

10.0 out of 10, Exceptional, (11)
"The location is perfect!"
The price is AED 893
AED 2,315 total
includes taxes & fees
16 Sep - 17 Sep
Fisher House: Steps From USNA + Covered Parking!

London Towne Bungalow w/Loft - Walk to the Beach!

8.0 out of 10, Very Good, (2)
"The water that comes out of the house tastes bad."
The price is AED 511
AED 1,681 total
includes taxes & fees
4 Sep - 5 Sep
London Towne Bungalow w/Loft - Walk to the Beach!

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (47)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is AED 735
AED 1,098 total
includes taxes & fees
8 Sep - 9 Sep
BAYSIDE BUNGALOW

Spacious 5 BR house - 5 Min Walk to N-MC Stadium!

9.0 out of 10, Wonderful, (2)
"My mom and I visited with 8 grandchildren as part of their Christmas present. We checked out the Naval Academy, monuments in DC, and a football bowl game. The kids enjoyed the new adventures!"
The price is AED 650
AED 2,282 total
includes taxes & fees
16 Sep - 17 Sep
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
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