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Holiday Homes in Chester

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Featured Holiday Homes in Chester

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 AU$484
includes taxes & fees
1 Sept - 2 Sept
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 AU$417
includes taxes & fees
28 Aug - 29 Aug
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 AU$417
includes taxes & fees
28 Aug - 29 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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 AU$238
includes taxes & fees
1 Sept - 2 Sept
Modern New Suite Close to US Capital and BWI Airport

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 AU$693
includes taxes & fees
8 Sept - 9 Sept
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
The price is AU$1,284
includes taxes & fees
28 Aug - 29 Aug
Gorgeous Creek Side Ranch-Style Estate With Dock

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AU$730
includes taxes & fees
1 Sept - 2 Sept
The Cottage

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 AU$651
includes taxes & fees
28 Aug - 29 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 AU$784
includes taxes & fees
28 Aug - 29 Aug
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."
The price is AU$781
includes taxes & fees
28 Aug - 29 Aug
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is AU$714
includes taxes & fees
1 Sept - 2 Sept
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 AU$612
includes taxes & fees
22 Sept - 23 Sept
Bayside Cottage steps from Rock Hall Harbor

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 AU$831
includes taxes & fees
1 Sept - 2 Sept
Cute bungalow blocks to Stadium

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AU$807
includes taxes & fees
9 Sept - 10 Sept
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

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

The price is AU$942
includes taxes & fees
1 Sept - 2 Sept
Historic 3 BR Home - 15 Min Walk to N-MC Stadium

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (21)
"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."
The price is AU$823
includes taxes & fees
28 Aug - 29 Aug
Edgewater/Mayo Gateaway w/ Hot Tub

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is AU$469
includes taxes & fees
28 Aug - 29 Aug
BAYSIDE BUNGALOW

Historic Row Home 1 Block from Gate 1 at USNA!

10.0 out of 10, Exceptional, (1)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
Historic Row Home 1 Block from Gate 1 at USNA!

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

The price is AU$504
includes taxes & fees
9 Sept - 10 Sept
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
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

Find out more about Chester

Find out more about Chester

Chester Holiday Homes information

Number of reviews
596
Accommodation
710 Holiday Homes
Lowest Price
AU$587
Highest Price
AU$587