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Vacation rentals in Charlestown

Vacation rentals in Charlestown

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Charlestown

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

  • Connecticut River-Cozy Cottage
    SUPERHOSTEntire guesthouse · 2 guests · 1 bed · 1 bath
    Connecticut River-Cozy Cottage

    This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

    What guests are saying:

    “I had a wonderful 3 week stay at Nicholas’ cabin. The area is quiet and there were many birds and other creatures about. The location is excellent for hiking as well. Nick was great with communication and flexible with some unforeseen issues - he even brought me some homemade potato salad and cake and on a snowy evening. Oh and my cat loved the screened patio. :) If you are looking for a cozy cabin retreat, I highly recommend staying here!”

  • Connecticut River Odyssey
    SUPERHOSTEntire apartment · 4 guests · 3 beds · 1 bath
    Connecticut River Odyssey

    Take a break from cities and enjoy social isolation in nature! Air exchange system and super sanitized between guests. If you’re healthy, come recreate on land or water. If you’re sick, you are welcome here to recover, just alert host so proper protection can be worn during cleaning and disinfecting after your stay. Water views from all rooms inside. Easy access to I-91. Private entry under a covered patio space which includes a grill and outdoor seating. Fire pit, too.

    What guests are saying:

    “Liz’s place was *perfect* for our ski weekend. It is only 30 min from Okemo and an hour from Killington. Her place allows guests a private entrance in back, with a convenient lock box. Your view is of the river - beautiful! The queen bed is very comfortable and the bedroom has a charming seaside theme. Plenty of closet space. She keeps it sparkling clean and fresh. She has thought of pretty much everything and provides a well stocked pantry and fridge (!) , kitchen appliances, cleaning supplies, binder of recommendations, laundry machines, local homemade maple soap, a chalkboard note to welcome us by name, etc. Our two kitties came with us and were very happy and relaxed there. Would love to return!”

  • Inviting studio apartment above barn in Vermont
    SUPERHOSTBarn · 4 guests · 2 beds · 1 bath
    Inviting studio apartment above barn in Vermont

    This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

    What guests are saying:

    “We chose this barn apartment for a ski weekend at Okemo Mountain. The pictures do not do the space justice at all. The drive up to the barn is beautiful in itself. The space is gorgeous, and the details provided by the host (farm fresh eggs! Hershey’s kisses! Coffee! A stocked medicine cabinet with toiletries!) were thoughtful and adorable. The barn is located a short drive to the mountain and the town of Chester has a couple of cute spots to eat (we loved Heritage Cafe for a pre-ski breakfast and coffee). Extra blankets and a postcard view....we loved it so much that we canceled our Airbnb for Burlington next month and rebooked with them for another ski weekend at Okemo next month.”

Holiday rentals for every style

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Popular amenities for Charlestown holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Charlestown

Camp on our farm (and gaze at the stars).
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Camp on our farm (and gaze at the stars).
Price:$57 AUD / night
The Stone Schoolhouse
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The Stone Schoolhouse
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"The Woodshed" Musician/Artist loft
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"The Woodshed" Musician/Artist loft
Price:$97 AUD / night
Beautiful rustic woods and fields retreat for two.
Entire cabin
Beautiful rustic woods and fields retreat for two.
Price:$84 AUD / night
Southern Vermont Getaway
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Price:$79 AUD / night
The Blue Room of Eva Blake House
SUPERHOSTPrivate room
The Blue Room of Eva Blake House
Price:$102 AUD / night
Cozy Village Cottage
SUPERHOSTEntire cottage
Cozy Village Cottage
Price:$144 AUD / night
Private Hilltop farm apartment
SUPERHOSTEntire house
Private Hilltop farm apartment
Price:$113 AUD / night
Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet
SUPERHOSTEntire apartment
Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet
Price:$133 AUD / night
Vermont Riverview 5802
SUPERHOSTEntire house
Vermont Riverview 5802
Price:$506 AUD / night
Meadowsweet Farm
SUPERHOSTPrivate room
Meadowsweet Farm
Price:$102 AUD / night
Tanglebloom Cabin | Glamping Nature Experience
SUPERHOSTFarm stay
Tanglebloom Cabin | Glamping Nature Experience
Price:$138 AUD / night
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