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Search Guest Houses in Chester

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Compare 6 Guest Houses in Chester with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (185)
"The place was very clean , had all the things in the home to make your stay wonderful!!!! Kitchen stocked with cooking equipment, towels for the pool, and the was owner was a great host."
Island Life! Kent Island Waterfront with Pool-Bring your boat!

Newly Renovated Guest House located in Oxford MD

9.8 out of 10, Exceptional, (20)
"We had a lovely time staying in this well situated VRBO. Everything was very clear and easy with check in/out and our stay in general. We love Oxford and know it well, and this location was well suited to visiting family. We would stay here again!"
Newly Renovated Guest House located in Oxford MD

Sandaway Suites & Beach

3.0 star property
9.2 out of 10, Wonderful, (134)
"It was a very relaxing stay!!"
The price is AED 1,063
AED 1,170 total
includes taxes & fees
9 Jun - 10 Jun
Sandaway Suites & Beach

Riverview Retreat on Warehouse Creek

10.0 out of 10, Exceptional, (22)
"Very clean, quiet, they provided everything. It was beautiful and peaceful. I would love to stay there again. "
The price is AED 639
AED 1,479 total
includes taxes & fees
12 May - 13 May
Riverview Retreat on Warehouse Creek

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

10.0 out of 10, Exceptional, (15)
"Very convenient! We really enjoyed our stay and the hosts were very accommodating! "
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

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
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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Other property types in Chester

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (14)
"Loved the location, the property, and amenities. Would definitely stay again!"
Waterfront Sunset Bayview: sleeps 6

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (215)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is AED 3,695
AED 5,749 total
includes taxes & fees
13 May - 14 May
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
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.