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Search Guest Houses in Chester

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Compare 5 Guest Houses in Chester with updated reviews, rates, and availability.

Ecotours
Sandaway Suites & Beach
3.0 star property
9.2 out of 10, Wonderful, (115)
"I took a solo trip and picked the perfect spot. This family owned inn is great for a family trip, a romantic getaway, or for a quiet escape by yourself. The owners are such a welcoming family and made me feel very like VIP. I will be going back and recommend Sandaway to anyone looking for that getaway in the Eastern Shore. Thank you Gibson Family for a wonderful experience!"
The price is $309
$340 total
includes taxes & fees
Jun 6 - Jun 7
Sandaway Suites & Beach
Fridge, microwave, oven, stovetop
Newly Renovated Guest House located in Oxford MD
10.0 out of 10, Exceptional, (8)
"A great getaway but could even be better if you were to have a comfortable lounger in the living room as well as a couple of loungers in the garden. Despite the lounger issue I would definitely rent again"
Newly Renovated Guest House located in Oxford MD
TV, offices
Riverview Retreat on Warehouse Creek
The price is $191
$415 total
includes taxes & fees
May 29 - May 30
Riverview Retreat on Warehouse Creek
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Fridge, microwave, oven, stovetop
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
10.0 out of 10, Exceptional, (12)
"Loved the stay here. Such a nice cute spot and so close to everything we needed."
The price is $185
$405 total
includes taxes & fees
Jun 3 - Jun 4
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Property grounds
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
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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.

Other property types in Chester

Interior
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (6)
"My sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass of wine as we watched the amazing sunset. We all agreed we would absolutely stay again in the future."
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
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.

Chester Guest Houses information

Number of reviews
142
Accommodation
5 Guest Houses
Lowest Price
$185
Highest Price
$309

Recent reviews of Chester hotels
Expedia verified reviews

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

5/5 Excellent
"All was good for our stay. There is a charge for parking which I did not see indicated on the website before booking. "
A verified traveler stayed at Hilton Garden Inn Annapolis
Posted 2 days ago
Hilton Garden Inn Annapolis