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.

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

10.0 out of 10, Exceptional, (16)
"This was a great property!! Gary and his family were very helpful and kind! The guest house area was gorgeous and very well kept. The dock and river was beautiful and peaceful. "
The price is SAR 559
SAR 1,362 total
includes taxes & fees
3 Dec - 4 Dec
Riverview Retreat on Warehouse Creek

Newly Renovated Guest House located in Oxford MD

10.0 out of 10, Exceptional, (16)
"Cute place within walking distance to town. "
Newly Renovated Guest House located in Oxford MD

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

10.0 out of 10, Exceptional, (13)
"Loved the stay here. Such a nice cute spot and so close to everything we needed."
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

Chesapeake Bayside Loft

The price is SAR 529
SAR 604 total
includes taxes & fees
27 Dec - 28 Dec
Chesapeake Bayside Loft
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

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

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

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.