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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Guest Houses in Chester

Sandaway Suites & Beach
Private beach, sun-loungers, kayaking, fishing

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (145)
"Beautiful historic building and rooms. Scenic, quiet grounds, calming views of the bay. A true gem !"
The price is AU$489
includes taxes & fees
1 Sept - 2 Sept
Sandaway Suites & Beach
Island Life! Kent Island Waterfront with Pool-Bring your boat!
3 bedrooms, iron/ironing board, travel cot, free WiFi

Island Life! Kent Island Waterfront with Pool-Bring your boat!

10.0 out of 10, Exceptional, (195)
"Wonderful house with great water access. Great place to relax and visit and recreate "
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Riverview Retreat on Warehouse Creek - sleeps 6
TV, fireplace, offices

Riverview Retreat on Warehouse Creek - sleeps 6

10.0 out of 10, Exceptional, (26)
"Very clean, quiet, they provided everything. It was beautiful and peaceful. I would love to stay there again. "
The price is AU$608
includes taxes & fees
26 Aug - 27 Aug
Riverview Retreat on Warehouse Creek - sleeps 6
Newly Renovated Guest House located in Oxford MD
Fridge, microwave, oven, stovetop

Newly Renovated Guest House located in Oxford MD

9.8 out of 10, Exceptional, (23)
"Clean and somewhat comfortable. "
Newly Renovated Guest House located in Oxford MD
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Fridge, microwave, oven, stovetop

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

10.0 out of 10, Exceptional, (18)
"Loved the stay here. Such a nice cute spot and so close to everything we needed."
The price is AU$503
includes taxes & fees
20 Aug - 21 Aug
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Calico Cottage Guest House
Terrace/patio

Calico Cottage Guest House

10.0 out of 10, Exceptional, (8)
"This tiny house is tastefully furnished and, coupled with the quiet neighborhood, provides a relaxing, peaceful environment."
Calico Cottage Guest House
The Shallow Creek Shore Shack on the Chesapeake Bay
Property grounds

The Shallow Creek Shore Shack on the Chesapeake Bay

10.0 out of 10, Exceptional, (24)
"Our stay was lovely, you can sit on the deck and see the water, or take a kayak out for a ride. Brendan is a great host and responsive during the stay!"
The Shallow Creek Shore Shack on the Chesapeake Bay
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Room was very clean and nice. Staff very friendly"
Allen 1-night trip
Posted 18 hours ago
Country Inn & Suites by Radisson, Annapolis, MD