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Vacation rentals in Chester River

Vacation rentals in Chester River

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester River

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Rivershore Retreat
    SUPERHOSTEntire cabin · 6 guests · 3 beds · 1.5 bathrooms
    Rivershore Retreat

    Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

    What guests are saying:

    “Perfection. From Paris to Thailand to New York we have stayed in memorable Airbnb’s places. Pj’s place has a charm you won’t find anywhere else. My wife and I plus our 2 rescue pups Bella & Stella had the time of our lives. Fresh flowers, all the kitchen ware you can imagine, a ready to be sparked fire-pit, super clean quarters, romantic sunsets, breathtaking sunrises, coupled with amazing communication. What else can you ask for? If you see this place available, don’t think it twice 😎🙌🏽🔥”

  • Cottage with Modern Updates - Walk to Waterfront!
    SUPERHOSTEntire cottage · 7 guests · 4 beds · 1 bathroom
    Cottage with Modern Updates - Walk to Waterfront!

    Historic cottage is fully renovated and located in the heart of Rock Hall. Features an open living area, modern kitchen, sunny front porch, big fenced backyard, and patio with picnic table. Enjoy everything the town has to offer - fishing, boating, festivals, dock bars, restaurants, shopping, & more. Walking distance to Main Street, marina, Harbor Shack, Waterman's Crab House, The Mainstay. A short drive to Eastern Neck National Wildlife Refuge, Washington College, historic Chestertown.

    What guests are saying:

    “We had a great time on our trip to Rock Hall. Meghann’s house was beautiful, well stocked, and was exactly what we were expecting. The only complaint I have is that the upstairs room gets very hot because there’s only one vent for the entire room. Luckily, it got cooler at night and we were finally able to cool off the room quicker. Other than that we have absolutely nothing negative to say. She stocked the home with many green earth-friendly products, which we thought was a really nice touch. I would definitely stay in her home again.”

  • Wye River Cottage and Horse Barn
    SUPERHOSTEntire cottage · 4 guests · 2 beds · 1.5 bathrooms
    Wye River Cottage and Horse Barn

    Unplug and unwind in our cozy, rustic wooden cottage, surrounded by over 20 wildlife enriched acres and situated right on the water of the Wye River. Imagine being immersed in a park-like wooded setting, surrounded by large trees and a gorgeous full accessible river. Perfect for guests who wish to bring kayaks or canoes Located just off of route 50 with access to shopping at the Queenstown Outlets. Our cottage is perfect for animal lovers, the outdoors-man, couples, seniors and small groups.

    What guests are saying:

    “My wife and I stayed in Rockys place after we got married. Rocky was very helpful and gave us plenty of tips. If you’re looking to get away from distractions and enjoy nature definitely book his place. He left us wine and flowers and offered to get rose petals since it was our wedding weekend. He also gave me some tips on where to go fishing. The fire pit was amazing and we really loved it there because it’s close to restaurants and other places but also far away from the business of local towns. If you love firm mattresses you will be in heaven and the couch is so comfy. Wonderful experience and this was my first air bnb stay. We will definitely be back!”

Holiday rentals for every style

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Popular amenities for Chester River holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chester River

Cottage by the Bay in Rock Hall, MD
SUPERHOSTEntire cottage
Cottage by the Bay in Rock Hall, MD
Price:€208 / night
Chester Riverfront At Kent Narrows
SUPERHOSTEntire flat
Chester Riverfront At Kent Narrows
Price:€172 / night
Eastern Shore Charm on Winchester Creek
SUPERHOSTEntire guest house
Eastern Shore Charm on Winchester Creek
Price:€102 / night
Beautiful Waterfront Chestertown Getaway
SUPERHOSTEntire guest suite
Beautiful Waterfront Chestertown Getaway
Price:€87 / night
RIVER WATCH
SUPERHOSTEntire flat
RIVER WATCH
Price:€185 / night
The Bittersweet
SUPERHOSTEntire flat
The Bittersweet
Price:€75 / night
Entire River Front Home - 4 Bedrooms 4.5 Baths
SUPERHOSTEntire house
Entire River Front Home - 4 Bedrooms 4.5 Baths
Price:€454 / night
Merry Manor 
Pet Friendly Home
SUPERHOSTEntire house
Merry Manor Pet Friendly Home
Price:€110 / night
Bayside Beach House
SUPERHOSTEntire house
Bayside Beach House
Price:€199 / night
Work from Home-Nature's Paradise! Private/Peaceful
Entire house
Work from Home-Nature's Paradise! Private/Peaceful
Price:€281 / night
Oyster Cottage
SUPERHOSTEntire cottage
Oyster Cottage
Price:€221 / night
83 steps to the beach...
SUPERHOSTEntire house
83 steps to the beach...
Price:€230 / night
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