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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

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

Newly Renovated Guest House located in Oxford MD
Enjoy time by the water

Newly Renovated Guest House located in Oxford MD

9.8 out of 10, Exceptional, (18)
"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
Beach

Sandaway Suites & Beach

3.0 star property
9.2 out of 10, Wonderful, (132)
"We really enjoyed our stay at the Sandaway. It was quiet and peaceful in a wonderful spot, right on the water, next to the yacht club. We loved walking around Oxford, a quaint and historic little town. A quick strolling over to the Market for breakfast sandwiches and the Social Cafe for great espresso based coffees and pastries. Contactless check-in was a breeze. Having prepaid, we found our designated parking spot, went to our room and our key was in the lock. Complimentary water bottles and...
Sandaway Suites & Beach
Riverview Retreat on Warehouse Creek
Living area

Riverview Retreat on Warehouse Creek

10.0 out of 10, Exceptional, (18)
"My kids and I fell in love with Riverview Retreat. I wanted a place to spend Thanksgiving with my daughter as she's in Baltimore for the next two years (we're in TX). I wanted something out of the city and Anapolis rentals were sold out. I expanded my search, found Riverview Retreat, and am so glad I did. RR is perhaps the most comfortable, beautiful rental on record for us (and we rent a lot). PLENTY of room for the four of us (and) our doodle. Large sectional we all piled on for movies, large...
The price is SAR 578
SAR 1,419 total
includes taxes & fees
2 Mar - 3 Mar
Riverview Retreat on Warehouse Creek
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Living area

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
Outdoor dining

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

Cass-N-Reel Luxury Houseboat
Exterior

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Exterior

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Front of Carpenter St. Cottage

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (173)
"Great location! Antique furniture in a well maintained beautiful old house. Exactly what we needed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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.