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.

Guest favourite

Cabin in Stowe

4.93 out of 5 average rating, 336 reviews

The Canopy House—Remodeled Vermont A-Frame Near Downtown

ElizabethRating, 5 stars2 weeks ago
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!
Guest favourite

Townhouse in Stowe

4.86 out of 5 average rating, 325 reviews

Carolyn's Rustic Modern Chalet

LouiseRating, 5 stars1 week ago
Super spacious and can’t beat the location. Would recommend to any large groups headed up to Stowe.
Guest favourite

Townhouse in Stowe

4.98 out of 5 average rating, 59 reviews

Stowe Depot townhouse - Fireplace -Deck- Rec Path

JohnRating, 5 stars2 weeks ago
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.
Guest favourite

Cabin in Barton

4.81 out of 5 average rating, 159 reviews

Charming lake cottage on Crystal Lake! Boats! R&R!

CharlesRating, 5 stars3 months ago
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!
Superhost

Guesthouse in Eden

4.87 out of 5 average rating, 271 reviews

Teeny Tiny Cottage on Lake Eden Water Front

CatherineRating, 5 stars3 months ago
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 ❤️
Superhost

Home in Eden

4.94 out of 5 average rating, 132 reviews

Cozy Lake Eden Retreat|Hot Tub|Wifi|Games|Pets OK

KimberlyRating, 5 stars3 weeks ago
Beautiful place, enjoyed it immensely, kids loved it here
Guest favourite

Home in Jay

5 out of 5 average rating, 23 reviews

Best Location | '24 Reno |Ski-In/Out by Waterpark

JosephRating, 5 stars4 days ago
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.
Superhost

Townhouse in Stowe

4.93 out of 5 average rating, 14 reviews

4 BR Home at Topnotch Resort & Spa, Stowe Vermont

JeffreyRating, 5 stars4 days ago
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!
Guest favourite

Apartment in Cambridge

4.93 out of 5 average rating, 45 reviews

Quiet Smuggs Retreat Ski in/out

DavidRating, 5 stars1 month ago
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.
Guest favourite

Apartment in Waterbury Center

4.98 out of 5 average rating, 62 reviews

Sir Richards Waterbury Stowe Lake View Escape 2Br

AnnaRating, 5 stars3 months ago
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.
Guest favourite

Townhouse in Stowe

4.89 out of 5 average rating, 161 reviews

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

JessicaRating, 5 stars3 months ago
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!
Superhost

Home in Stowe

4.82 out of 5 average rating, 154 reviews

Great For Large Groups with Hot Tub

Bianca DayRating, 5 stars2 weeks ago
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!

Popular amenities for Charleston holiday rentals

Stay near Charleston's top sights

The Gap Pub & Grill26 locals recommend
Clyde River Recreation LET'S GO KAYAKING23 locals recommend
NorthWoods Stewardship Center13 locals recommend
WilloughVale Inn & Restaurant9 locals recommend
Willoughby Lake Beach9 locals recommend
Evansville Trading Post & True Value7 locals recommend

Other great holiday rentals in Charleston

Guest favourite

Chalet in Sutton

4.92 out of 5 average rating, 244 reviews

Cabin Sutton 264 - Relaxation en pleine nature !

CordeliaRating, 5 stars3 weeks ago
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.
Guest favourite

Home in Stowe

4.94 out of 5 average rating, 66 reviews

Charming and quiet rental for family or friends

BrianRating, 5 stars2 weeks ago
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.
Guest favourite

Home in Stowe

4.97 out of 5 average rating, 114 reviews

Cozy Mountain Home w/Million $ View

JoAnnaRating, 5 stars4 weeks ago
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!
Guest favourite

Home in Stowe

4.98 out of 5 average rating, 155 reviews

Spacious Eco-Friendly Stowe Home for Family Fun

KatherineRating, 5 stars2 months ago
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.
Superhost

Villa in Stowe

4.82 out of 5 average rating, 45 reviews

Beautiful 5 Bedroom Villa with Amazing Views

RichardRating, 5 stars3 weeks ago
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.
Guest favourite

Home in Westmore

4.92 out of 5 average rating, 60 reviews

New Vacation Home w/Awesome View!

BarbaraRating, 5 stars2 months ago
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.
Superhost

Home in Derby

4.81 out of 5 average rating, 43 reviews

Lake Salem House

ChristopherRating, 5 stars5 months ago
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.
Guest favourite

Holiday home in Stowe

4.95 out of 5 average rating, 22 reviews

Great location! Spacious 3 Bedroom, 2 bath unit.

NathanRating, 5 stars3 months ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Orleans County
  5. Charleston