Holiday houses in Charleston
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Top-rated holiday rentals in Charleston
Guests agree: these stays are highly rated for location, cleanliness and more.
Cabin in Stowe
4.93 out of 5 average rating, 336 reviewsThe Canopy House—Remodeled Vermont A-Frame Near Downtown
Ryan’s cabin is the perfect getaway for a group! We had a wonderful and cozy time cooking, playing games, and enjoying the fire in this incredible space. A total gem!
Townhouse in Stowe
4.86 out of 5 average rating, 325 reviewsCarolyn's Rustic Modern Chalet
Super spacious and can’t beat the location. Would recommend to any large groups headed up to Stowe.
Townhouse in Stowe
4.98 out of 5 average rating, 59 reviewsStowe Depot townhouse - Fireplace -Deck- Rec Path
Had a short, but wonderful stay for business and family. In town location made it super convenient to walk to restaurants, shops, and free bus to Stowe resort. House is just as pictured. Was clean and had plenty of supplies for kitchen, bath and beds. Snow removal on common sidewalks and parking lot was efficient. Wonderful host. Would definitely stay here again.
Cabin in Barton
4.81 out of 5 average rating, 159 reviewsCharming lake cottage on Crystal Lake! Boats! R&R!
Darren is a great host, and this is a great place! He had plenty of great recommendations in the area, so we always had something to do. The lake itself is super pretty and very tranquil. Would highly recommend!
Guesthouse in Eden
4.87 out of 5 average rating, 271 reviewsTeeny Tiny Cottage on Lake Eden Water Front
This was the most beautiful, peaceful spot to stay for the long weekend. Eric was super helpful, met us upon our arrival, gave us suggestions for places to go and eat. The cottage was spotlessly clean and comfortable. We loved it ❤️
Home in Eden
4.94 out of 5 average rating, 132 reviewsCozy Lake Eden Retreat|Hot Tub|Wifi|Games|Pets OK
Beautiful place, enjoyed it immensely, kids loved it here
Home in Jay
5 out of 5 average rating, 23 reviewsBest Location | '24 Reno |Ski-In/Out by Waterpark
The ski in ski out is amazing, very easy to access the Tram Side Base and get the day going. Jay peak is beautiful and the location is great. Steven was always very responsive and helpful. Would definitely stay here again.
Townhouse in Stowe
4.93 out of 5 average rating, 14 reviews4 BR Home at Topnotch Resort & Spa, Stowe Vermont
Second time staying at Stowe Resort Homes place in Topnotch. Lovely place and perfect for ski weekend away from Boston. Very easy check-in and check-out procedures. Beautiful home and super comfortable and close to the mountain. Thanks again!
Apartment in Cambridge
4.93 out of 5 average rating, 45 reviewsQuiet Smuggs Retreat Ski in/out
Absolutely beautiful condo. This is exactly what me and my kids were looking for. Ski in, ski out. Updated amenities and just all around great place.
Apartment in Waterbury Center
4.98 out of 5 average rating, 62 reviewsSir Richards Waterbury Stowe Lake View Escape 2Br
We thoroughly enjoyed our stay in this unique apartment. Barbara went out of her way to make sure we had and could find everything we needed. We especially loved the view - every morning we woke to a beautiful and ever changing landscape.
Townhouse in Stowe
4.89 out of 5 average rating, 161 reviewsStowe, Topnotch Resort-Best Mt & Luxury in Vermont
What an amazing home! We had a very smooth check-in thanks to Alex and Kathy - even with little kids who were hungry and fussy. The condo was perfect. The living and dining areas were large enough to feel comfortable and conveniently laid out. The bedrooms were large and it was nice to have two bathrooms. We had spectacular weather and enjoyed the outdoors on and off resort property. Highly recommend this rental!
Home in Stowe
4.82 out of 5 average rating, 154 reviewsGreat For Large Groups with Hot Tub
Spacious house (even better than the photos), lovely view, great location. Most importantly - incredibly accommodating and responsive host (flexible check in and out times). Stayed here for our annual friend group ski trip and the group all gave this house rave reviews. We would love to come back! Thank you Linda!
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Other great holiday rentals in Charleston
Chalet in Sutton
4.92 out of 5 average rating, 244 reviewsCabin Sutton 264 - Relaxation en pleine nature !
Such a great location for a quick nourishing retreat or getaway that has all the conveniences to make the stay one that is Homie and relaxing or supportive of adventuring and going out. Any support and communications between Erik and us were professional, responsive, and impressively speedy. All the aspects of the day are very comfortable and mindfully curated as well thought out. We loved the shower design, hot tub, grill, and wood fired stove. We have very much appreciated the privacy and the easy access to adorable Sutton.
Home in Stowe
4.94 out of 5 average rating, 66 reviewsCharming and quiet rental for family or friends
Liza’s home was beautiful, and it couldn’t be closer to Stowe Mountain Resort. It was the perfect ski trip house for my group, and the host was incredibly accommodating and helpful.
Home in Stowe
4.97 out of 5 average rating, 114 reviewsCozy Mountain Home w/Million $ View
Daveo was a great host. This was the perfect spot for our friends, kids and dogs! We stayed on New Years Eve and were able to see the Stowe mountain and town fireworks from the living room and deck! It was a great, cozy, space for a family getaway and ski weekend!
Home in Stowe
4.98 out of 5 average rating, 155 reviewsSpacious Eco-Friendly Stowe Home for Family Fun
My family of 8 (+2 dogs) had a wonderful weekend at Susan’s place! We all had PLENTY of room to spread out as the home was very spacious. Susan’s home was so welcoming and we immediately felt comfortable upon check in. The location was perfect and just about 15 minutes from all local attractions in Stowe! The kitchen was extremely well stocked and we had everything we needed for family meals. We loved our stay and would highly recommend booking this property. Susan was responsive and very kind when we had questions.
Villa in Stowe
4.82 out of 5 average rating, 45 reviewsBeautiful 5 Bedroom Villa with Amazing Views
Very nice home with great amenities. Great location to and from everything. Nicely distributed with space for everyone. Beds were comfortable and the home has plenty of towels etc. Overall it was a great place for weekend or longer. Maria was easy to communicate with and there were no issues.
Home in Westmore
4.92 out of 5 average rating, 60 reviewsNew Vacation Home w/Awesome View!
I was looking for a place to watch the leaves change for the month of October and I found it. The pictures do not do this home justice. It is more spacious than I thought and the views are even more spectacular in person. Access to all parts of Lake Willoughby and room for two distinct groups or families with upstairs and downstairs bedrooms and a midlevel with open concept kitchen, living and dining areas and a full bath and washer/dryer. It is COMPLETELY stocked with everything you need for an extended stay. Incredibly peaceful and I hope I am lucky enough to visit again.
Home in Derby
4.81 out of 5 average rating, 43 reviewsLake Salem House
Margaret's house was ideal for our vacation. We especially liked the kayaks and the entry to the lake, the grill, and the lovely back porch, which accommodated many family members of all ages. We took side trips to Canada, Glover, and Lake Willoughby. We ordered pizza from Hoagies for our first night, since we figured nobody would want to cook. We saw a bald eagle, completed a jigsaw puzzle and built an epic Jenga. I made a mistake by not pulling the Casella trash bin closer to the road on Wednesday night. Maybe that requirement could be put into the "house rules" part of the website? Margaret was always available to answer our questions, replying immediately to our texts. If anything, her kitchen is "over-stocked" with pantry items (maybe from previous guests?), which included lots of helpful Tupperware. The lake is beautiful , with few motorboats to disturb the calm. We'd love to come back.
Holiday home in Stowe
4.95 out of 5 average rating, 22 reviewsGreat location! Spacious 3 Bedroom, 2 bath unit.
Great home base for exploring Stowe. The house was very clean and description was accurate. Very close to great restaurants, breweries and the bike path.
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
Wi-Fi availability
60 properties include access to Wi-Fi
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