Photo by Patricia Knorr

Search Guest Houses in Chester

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Compare 5 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, (183)
"Our host Jon was so nice, checked in with us to make sure all was good, and it was. He had the place decorated for Christmas and even had a tree - we appreciated it very much since we were not home for Christmas. Beautiful setting on Cox creek. The guest house was well maintained and fully equipped kitchen. Very Comfortable beds and bedding which we find unique for VRBOs. "
Island Life! Kent Island Waterfront with Pool-Bring your boat!

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

3.0 star property
9.2 out of 10, Wonderful, (133)
"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...
The price is AED 805
AED 885 total
includes taxes & fees
28 Apr - 29 Apr
Sandaway Suites & Beach

Riverview Retreat on Warehouse Creek

10.0 out of 10, Exceptional, (21)
"The property was beautiful and conveniently located between Baltimore and DC, not far from Annapolis. The owners were VERY helpful. It was very easy to access the property. (Sometimes we've had trouble finding the entrance or getting locks to work - no problems here what so ever) We had use of kayaks and paddle boards for the river, which was great for my teenage son. The owners gave great recommendations for local restaurants. The property is in a walkout basement which you access via a path....
The price is AED 511
AED 1,287 total
includes taxes & fees
30 Apr - 1 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, (12)
"Great house, great owner, family had a blast! Thank you!"
Waterfront Sunset Bayview: sleeps 6

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

10.0 out of 10, Exceptional, (210)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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.