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Holiday Homes in Chester

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Featured Holiday Homes in Chester and around

Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is €230
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
❤️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 €236
includes taxes & fees
21 Oct - 22 Oct
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (6)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
The price is €392
includes taxes & fees
27 Oct - 28 Oct
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
The price is €236
includes taxes & fees
25 Oct - 26 Oct
Chesapeake Bay Harbor View in a central location to events/restaurants
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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. "
The price is €362
includes taxes & fees
17 Oct - 18 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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 €311
includes taxes & fees
21 Oct - 22 Oct
Bayside Cottage steps from Rock Hall Harbor
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (5)
"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."
Charming Pet-Friendly Stay - Near Bay & Beaches.
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
The price is €266
includes taxes & fees
19 Oct - 20 Oct
BAYSIDE BUNGALOW
Walk to Beach! King Bed & Free Beach Passes
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!"
The price is €332
includes taxes & fees
20 Oct - 21 Oct
Walk to Beach! King Bed & Free Beach Passes
Modern New Suite Close to US Capital and BWI Airport
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! "
The price is €128
includes taxes & fees
19 Oct - 20 Oct
Modern New Suite Close to US Capital and BWI Airport
Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (28)
"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."
The price is €287
includes taxes & fees
2 Nov - 3 Nov
Large 2 bedroom house with private parking in a nice neighborhood
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (3)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
The price is €378
includes taxes & fees
19 Oct - 20 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (3)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
The price is €568
includes taxes & fees
26 Oct - 27 Oct
Annapolis Retreat - 7 mins from downtown Annapolis!
The Hideaway Spot- Waterfront w/ Dock on Long Cove
8.4 out of 10, Very good, (7)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
The price is €321
includes taxes & fees
3 Nov - 4 Nov
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is €457
includes taxes & fees
3 Nov - 4 Nov
Holly Hill Haven - Sleeps 10
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is €450
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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. "
The price is €439
includes taxes & fees
19 Oct - 20 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
The price is €480
includes taxes & fees
20 Oct - 21 Oct
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Neptune by the Water - Pet Friendly Fenced Yard
9.6 out of 10, Exceptional, (10)
"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! "
The price is €883
includes taxes & fees
14 Nov - 15 Nov
Neptune by the Water - Pet Friendly Fenced Yard
Cute bungalow blocks to Stadium
10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is €450
includes taxes & fees
21 Oct - 22 Oct
Cute bungalow blocks to 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

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Chester Holiday Homes information

Number of reviews
253
Accommodation
688 Holiday Homes
Lowest Price
€128
Highest Price
€883

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