
Holiday rentals in Charleston
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Top-rated holiday rentals in Charleston
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Charleston holiday rentals
Other great holiday rentals in Charleston
Guest favourite

Cottage in Derby
4.98 out of 5 average rating, 50 reviewsVermont Lakefront Cottage Getaway
FlipRating, 5 stars7 months ago
Doug was a great host and his place is beautiful.
Top guest favourite

Cabin in Newark
5 out of 5 average rating, 36 reviewsThe Hut: A Romantic Escape to the Kingdom
MichaelRating, 5 stars5 days ago
Loved our stay, not too far from a few towns. Quiet and quaint, which was an amazing break from our busy lives.
Top guest favourite

Cabin in Westmore
4.86 out of 5 average rating, 21 reviewsNEK Cordwood Cabin near Burke Mountain/Willoughby
KellyRating, 5 stars7 months ago
Gale was an amazing host! She accommodated some specific needs we had and was an excellent communicator. The house is so cozy and located in such a beautiful spot.
Guest favourite

Home in Westmore
4.88 out of 5 average rating, 26 reviewsLake Willoughby 1/4 mile away. Beaches and hiking!
SeanRating, 5 stars1 month ago
We had a lovely stay at Nancy’s place! The home was clean, cozy, and thoughtfully prepared. Nancy was warm, responsive, and made us feel very welcome. Would definitely stay again!
Superhost

Flat in Newport
4.8 out of 5 average rating, 76 reviewsMother in Law Guest Suite.
KatyRating, 5 stars4 days ago
thr most amazing host. so friendly and responsive when messaging back in forth. thr views and area were beautiful a 5 min drive down into town. made me not want to leave ! the place was so clean and homey. my son ended up staying and she brought in more towels and a bottle of vermont maple syrup.
Superhost

Apartment in Brighton
4.84 out of 5 average rating, 82 reviewsPeaceful Country Cabin
BarbaraRating, 5 stars3 weeks ago
Nice quiet location. Great view! Loved having a full kitchen.
Top guest favourite

Barn in Derby
5 out of 5 average rating, 43 reviewsThe Loft
MelanieRating, 5 stars2 weeks ago
Larry's place was exactly what we needed. We only stayed one night, but wished we had longer to stay. Larry was extremely clear in describing how to get there, communicated some important details to us, and when we needed some help, was very fast and helpful. I love the unique feel of the woodwork inside the loft apartment, and we enjoyed the extremely quiet surroundings. I highly recommend this place!
Top guest favourite

Cabin in Derby
4.94 out of 5 average rating, 51 reviewsSecluded Cabin on Large Private Pond and 200 Acres
DianRating, 5 stars9 months ago
A magical place. Geese migrating every morning and evening, exploring the pond in their rowboat, turtles, great blue heron, king fisher, frogs, great hikes through the woods, so many mushrooms, mosses, pines, the deck, screened-in porch, great bed, well stocked kitchen - we loved it all. Thank you!
Quick stats about holiday rentals in Charleston
Total rentals
70 properties
Total number of reviews
2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Destinations to explore
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- Rentals with lake access Charleston
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- Jay Peak Resort
- Smugglers' Notch Resort
- Ski Bromont
- Owl's Head
- Mont Sutton Ski Resort
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- Spruce Peak
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- Mt. Eustis Ski Hill
- Le Vignoble du Ruisseau - Winery & Cidery
- Val Caudalies - Vignoble & Cidrerie
- Mount Prospect Ski Tow
- Country Club of Vermont
- Domaine Cotes d'Ardoise - Winery & Cidery