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Vacation rentals in Centreville

Vacation rentals in Centreville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Centreville

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

  • Radcliffe Roost: Walk to College & Downtown
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
    Radcliffe Roost: Walk to College & Downtown

    Waterfront property on a peaceful creek. Ideally located in quiet neighborhood, 10-minute walk to Washington College and historic Chestertown. Private floor with two bedrooms, full private bath with beautiful large shower. Kitchenette has microwave, mini fridge, and coffee maker. $20 fee for each additional person over 2. Free parking. WIFI. Shared entrance with me but privacy assured. Hiking/biking, farmer's market, cute shops and restaurants easy walking distance. No cleaning fee or deposit.

    What guests are saying:

    “Hi Jan. Mike and I had a wonderful stay at your lovely Airbnb. You were so kind and thoughtful to all the special details. Everything was fresh and clean and we loved the tea/coffee and biscuit station. You were great at keeping in touch and remaining flexible to our arrival time. Nacho is a sweet and friendly greeter waiting at the door with his tail wagging. My only regret is not being able to stay longer! Thank you so much for opening up your charming house to us! Cheers... Anne and Mike Province”

  • The Bittersweet
    Entire apartment · 4 guests · 2 beds · 1 bath
    The Bittersweet

    A spacious private apartment right in the heart of beautiful downtown Chestertown! With food, drinks, and shopping literally steps from your front door, it doesn't get better than this. The Bittersweet Apartment is a subsidy of The White Swan Tavern.

    What guests are saying:

    “Cute spacious 1 bedroom apartment right in the heart of downtown Chestertown. Communication with Sarah was great. We loved the place. You can pretty much walk to everything from this location. There is a large living room, full kitchen and nice sized bedroom with a king bed and 1 bathroom. It was perfect for us and we would definitely stay here again!”

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

    “This cottage was amazing. It's set back in the woods and exactly what my wife and I were looking for. The back yard has a large stream with a dock and there is also a fire pit area . It was great to have coffee on the dock watching the sunrise. The cottage was very clean and cozy. Two large bedrooms and a big open kitchen and living room area. There is also a large enclosed porch overlooking the back yard. Rocky was a wonderful host, very quick to respond to my messages and Rocky made sure we had everything we needed during our stay. The property was set back off the highway a bit so it was very quiet but it was super easy to get everywhere we need to go. Thanks Rocky!!”

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Centreville vacation rentals

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

Other great vacation rentals in Centreville

Quiet Eastern Shore Nest
SUPERHOSTPrivate room
Quiet Eastern Shore Nest
Price:$53 CAD/night
Quiet and welcoming
SUPERHOSTPrivate room
Quiet and welcoming
Price:$88 CAD/night
Cape Cod Bed and Bath
Private room
Cape Cod Bed and Bath
Price:$115 CAD/night
Halcyon house.  Lovely views on MD eastern shore.
SUPERHOSTEntire apartment
Halcyon house. Lovely views on MD eastern shore.
Price:$169 CAD/night
Cozy apartment with amazing pool!
Entire guest suite
Cozy apartment with amazing pool!
Price:$88 CAD/night
Merry Manor 
Pet Friendly Home
SUPERHOSTEntire house
Merry Manor Pet Friendly Home
Price:$169 CAD/night
Riverton Retreat (queen bed)
SUPERHOSTPrivate room
Riverton Retreat (queen bed)
Price:$120 CAD/night
Pirates Perch
SUPERHOSTEntire house
Pirates Perch
Price:$203 CAD/night
Bayside Air (bnb)
SUPERHOSTPrivate room
Bayside Air (bnb)
Price:$162 CAD/night
Rustic & Elegant Private Bed & Bath
SUPERHOSTPrivate room
Rustic & Elegant Private Bed & Bath
Price:$133 CAD/night
Boutique by the Bay
SUPERHOSTEntire apartment
Boutique by the Bay
Price:$237 CAD/night
Beautiful Waterfront Chestertown Getaway
SUPERHOSTEntire guest suite
Beautiful Waterfront Chestertown Getaway
Price:$134 CAD/night
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