Holiday rentals in Charleston

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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
Cottage in Derby
4.98 out of 5 average rating, 56 reviews

On Golden Lake Salem

MeaganRating, 5 stars5 months ago
This cute lake cottage is the perfect place to get away and enjoy everything the lake and area has to offer. We watched sunsets, star gazed (saw the Milky Way), enjoyed the boats that were available to use and mainly hung out on the sun porch that had great views of the lake.
Superhost
Home in Stowe
4.94 out of 5 average rating, 66 reviews

Charming and quiet rental for family or friends

BrianRating, 5 stars1 month 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.
Superhost
Villa in Stowe
4.82 out of 5 average rating, 45 reviews

Beautiful 5 Bedroom Villa with Amazing Views

RichardRating, 5 stars2 months 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.
Top guest favourite
Home in Westmore
4.92 out of 5 average rating, 60 reviews

New Vacation Home w/Awesome View!

BarbaraRating, 5 stars4 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
Villa in Waterbury
4.95 out of 5 average rating, 43 reviews

Safe Mountain Retreat for Families & Friends

MonicaRating, 5 stars1 week ago
Sibylle is a proactive and gracious host. This is a great spot for anyone who considers themselves a "planner" and wants a weekend away with family friends in a pristine home. The place was perfect for entertaining both kids and adults. Very close to both Stowe and Bolton for skiing. What a special place!
Superhost
Home in Glover
4.84 out of 5 average rating, 19 reviews

Cheerful 5-bedroom house offered by Lakeside Haven

JessicaRating, 5 stars2 months ago
The house was the cleanest we have ever stayed at. The pictures actually don’t show how beautiful the space truly is! As mentioned in other posts, you do need to know that there is little privacy (no noise deadening) in the upstairs bathroom. Four of the bedrooms had privacy, one is a loft type area that you have to walk past to get downstairs. These two super minor things were not an issue for us and we had 4 teenage boys with us but may be good to know for others booking. The house was amazing and we would love to come back next year!
Top guest favourite
Cabin in Eden
5 out of 5 average rating, 6 reviews

Simply Eden- cabin 1

DesireeRating, 5 stars2 weeks ago
This Airbnb was perfect for my husband, dog & I! It was super clean, cozy, welcoming & quiet - just what we were looking for! We had the pleasure of meeting Sherry and she is so friendly! We had a great weekend exploring Vermont. Can’t wait to come back!
Superhost
Home in Stowe
5 out of 5 average rating, 5 reviews

Endless Views

TrevorRating, 5 stars13 months ago
The house and the property were beautiful and very relaxing. We had six of us staying there for four nights and we never felt cramped or on top of each other. The kitchen was well stocked with supplies and cooking utensils. There was not a shortage of fire wood either which we used every night. The fire place and seating around it made for a relaxing and cozy place to hang out and relax. The property was like a setting right of a post card. We traveled from Florida to have fun in the snow and there was plenty of it. Having 10 acres of woods and hills to explore was perfect. The house is also conveniently located from the Burlington Airport, the town of Stowe and the slopes making it easy to get to and from places, but still offering up the feeling of being away from the hustle and bustle of the town. We would definitely stay at this house again!

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

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