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Check prices for these dates

Next weekend
Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Price Vacation Homes

Pet-Friendly Home on Chester River w/ Dock!
Relax in a spacious, open-plan room with multiple seating areas and large windows offering a view of the outdoors.

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (13)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (43)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is CA $275
CA $411 total
includes taxes & fees
Aug 12 - Aug 13
BAYSIDE BUNGALOW
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Enjoy a meal with a view of the ocean from this dining area with large windows.

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a granite countertop.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (20)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Riverfront Denton Estate on 7 Acres w/ Fire Pit!
Stunning hallway with a chandelier, large mirror, and bookshelf.

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (10)
"The property is a great place to get away and enjoy some time with family. We enjoyed swimming in the pool. Fishing was fun as well catfish for days. Nice sunsets by the fire and just overall a great time with the family. "
Riverfront Denton Estate on 7 Acres w/ Fire Pit!
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Enjoy a meal with a view from the kitchen's glass doors, which lead to a patio with a deck and seating area overlooking a serene landscape.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (54)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront Estate w Private Pier, Game Room & Bar
Enjoy a leisurely game of pool or foosball in this spacious indoor recreation area with a pool table and foosball table.

Waterfront Estate w Private Pier, Game Room & Bar

9.8 out of 10, Exceptional, (30)
"Overall, our stay was fantastic. The weather was absolutely magnificent the entire stay."
Waterfront Estate w Private Pier, Game Room & Bar
Entire Townhouse in Rock Hall
Enjoy a serene retreat on this two-story home's spacious porch, surrounded by lush greenery and a well-maintained lawn.

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (30)
"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "
Entire Townhouse in Rock Hall
Peaceful Queenstown Home w/ Deck & Grill!
Enjoy cooking in this well-equipped kitchen with a central island, ample counter space, and appliances.

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Very cozy, a very quiet home"
Peaceful Queenstown Home w/ Deck & Grill!
River Front, Private Single Family Home
Enjoy a peaceful moment on the pier with a pair of Adirondack chairs and a small table.

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (16)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Stroll through the beautifully manicured lawn to the charming entrance, flanked by a picket fence and a garage with a covered porch.

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

10.0 out of 10, Exceptional, (20)
"Extremely clean, comfortable, and cozy place to stay for a weekend trip. The host was great to work with. We would definitely stay again."
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Grasonville Home w/ Private Pool on the Water
Relax by the serene pool overlooking the lake, surrounded by a lawn and shaded by a large tree.

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Stylish single-story home with a symmetrical facade, featuring evenly spaced windows and a central entrance.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $344
CA $576 total
includes taxes & fees
Aug 12 - Aug 13
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Stay in the landmark Lighthouse!
Enjoy serene views of the calm body of water from the breakwater.

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (103)
"Great views, unique living space and all the amenities. Really enjoyed our stay!"
Stay in the landmark Lighthouse!
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Enjoy a serene beach experience with a natural barrier of rocks separating the calm sea from the sandy shore.

Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD

10.0 out of 10, Exceptional, (19)
"We really enjoyed our stay in Rock Hall! Perfect house in a great location."
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
RELAX- Eastern Shore Creek Home - 6 Guests
Cozy up by the fireplace in this inviting living room with a stunning view of the outdoors.

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (3)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home - 6 Guests
Serene Waterfront Cottage with dock and gorgeous views.
Enjoy cooking in this well-equipped kitchen with a large island and modern appliances.

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Escape to a charming cottage surrounded by lush greenery and trees, with a cozy porch and a brick chimney.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (83)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Relax in a serene hot tub under a covered pergola with a breathtaking view of the surrounding landscape.

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is CA $271
CA $613 total
includes taxes & fees
Aug 12 - Aug 13
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Gorgeous Creek Side Ranch-Style Estate With Dock
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, oven, and wine cooler.

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock
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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Top Price Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Located close to restaurant "
Charles 2-night trip
Posted 3 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG