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Vacation rentals in Charleston

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Top-rated vacation rentals in Charleston

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

Guest favorite

Cabin in Stowe

4.93 out of 5 average rating, 336 reviews

The Canopy House—Remodeled Vermont A-Frame Near Downtown

Awarded as one of the top Airbnb's in New England by Condé Nast and Boston Globe! Featured on multiple global publications. Watch the snowflakes fall from the comfort of the 6-person outdoor hot tub, with first-class stargazing to be had all year long. Back inside, the vaulted interior features OM Home Furniture, while a 50” TV with soundbar sits above a real fire. Less than a two mile drive to all downtown Stowe has to offer. 3 BD 2 BA modern A-Frame with two living rooms, 6 person hot tub, Fireplace, two new Roku TV's , soundbar, AC unit, WiFi, deck and back patio, rainfall shower, high-end mattresses, Sonos speaker and furnished by OM Home Furniture. Close to Main Street, 5 miles to Von Trapp, 9 miles to Stowe Mountain Resort and .5 miles from rte 100 to get you easily in and out of town. you will have access to entire house accept for one personal closet in back downstairs bedroom. Less than a 2-mile drive to downtown Stowe, this home is on a hill just off Route 100. Nearby Von Trapp is full of restaurants and other amenities. Ski and snowboard from Stowe Mountain Resort 9 miles away, with picturesque hiking in the summer. I would highly recommend a four wheel or all wheel drive vehicle. House is on a hill with a pretty steep road leading to it.

Guest favorite

Townhouse in Stowe

4.86 out of 5 average rating, 325 reviews

Carolyn's Rustic Modern Chalet

Beautiful Stowe Historic Village 4BR 4bath with rustic modern interior. This is truly a luxury condo 2600SF living space, granite, stainless steel and hardwood. The level of detail is impressive. Walk to everything, restaurants, bars, supermarket, town hall, and the Mountain Shuttle to Stowe Mountain Resort. This private view of, and access to, Sunset Rock conservation land is rare in Stowe Village. The setting is private and park like. Hike/ bike out of your heated garage. Easy Rec Path access.

Guest favorite

Townhouse in Stowe

4.98 out of 5 average rating, 59 reviews

Stowe Depot townhouse - Fireplace -Deck- Rec Path

Spacious Village townhome in Stowe, in walking distance to many shops, restaurants and Park. The Master suite has a King bed, 40" HDTV, and an en-suite bathroom with Jacuzzi tub. The second bedroom has a queen bed, 27" HDTV and an en-suite bathroom. Beautiful kitchen with granite counters, coffee maker and grinder. Living room features a gas fireplace, smart TV and nice furniture. There is a comfortable Murphy bed and an air mattress for additional guests, plus a nice covered deck to enjoy!

Guest favorite

Cabin in Barton

4.81 out of 5 average rating, 159 reviews

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

Lakeview Cottage is adorable and located on one of Vermont's cleanest and most beautiful lakes, Crystal Lake! It's in the heart of the Northeast Kingdom, in the charming town of Barton. Sit around the outdoor firepit and soak in the view! You're just steps away from beaches and a dock. You'll find great swimming, fishing, boating, hiking, golfing, and mountain biking. Use our canoe or kayaks! Plus, Hill Farmstead Brewery is a short drive away. Beers there are rated best in the world!

Superhost

Guesthouse in Eden

4.87 out of 5 average rating, 271 reviews

Teeny Tiny Cottage on Lake Eden Water Front

This cozy cottage with loft on water front, $65 dollars per nights, Two night minimum is required. We have week or month reservations. Depending on availability there is rental of (2) paddle boats (2), kayaks, (1) two man canoe, dock spaces for rent for personal water craft. Travel to Burlington airport is one hour and Montreal airports is two hours. The cottage is centrally located between major ski areas, 30 minutes to Jay Peak Resort, Stowe Resort, and Smugglers Notch Resort.

Superhost

Home in Eden

4.94 out of 5 average rating, 132 reviews

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

Enjoy a quintessential Vermont getaway at this lakefront home. It’s the perfect place for remote workers and families looking for a perfect base for outdoor activities. Relax in then hot tub & admire gorgeous lake views, and enjoy direct access to the water. Rainy days are no less fun, with a game room and fireplace to keep you busy. Lake Eden –Frontyard! Eden Ethical Dog Sledding – 8 Min Drive Stowe – 30 Min Drive Create Lasting Memories In Eden With Us & Learn More Below!

Guest favorite

Home in Jay

5 out of 5 average rating, 23 reviews

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

Completely remodeled in 2024. Ski-in / Ski-out. Cannot beat the location! Steps to the water park, ice rink, tram, restaurants, and bars. Enjoy an upscale two story, 3 bed, 2 bath family-friendly luxury condo with a private back deck & small yard. You do not have to use your car at all. Quiet corner unit with no one above or below you. Each guest will be given a unique door code prior to check-in. Kitchen and linens are very well stocked. Well behaved dogs welcomed.

Superhost

Townhouse in Stowe

4.93 out of 5 average rating, 14 reviews

4 BR Home at Topnotch Resort & Spa, Stowe Vermont

Indulge yourself and your loved ones in this luxurious yet relaxed home, situated at the magnificent Topnotch Spa & Tennis Resort. All our Overlook Resort Homes at Topnotch feature the same stunning floor plan, with unique furnishings and decor that reflect the tastes of their owners. This lavish 4-bedroom, 4-bath Resort Home boasts exquisite Restoration Hardware furnishings and a well-appointed kitchen with brand new stone counters and stainless steel appliances.

Guest favorite

Apartment in Cambridge

4.93 out of 5 average rating, 45 reviews

Quiet Smuggs Retreat Ski in/out

Studio condo, end unit, first floor If you are looking for a memorable family vacation, look no further! Our newly renovated condo is perfect for a small family or group of friends. This ground-floor, end-unit studio, is situated just a short walk/ride away from the Village lift. Our condo is centrally located just steps away from the Village Green making it easy to get to all of the festivals and activities including the weekly Fireworks show on Thursday night.

Guest favorite

Apartment in Waterbury Center

4.98 out of 5 average rating, 62 reviews

Sir Richards Waterbury Stowe Lake View Escape 2Br

A fun, filled, peaceful property surrounded by nature. Drift into an amazing, relaxed state sitting on the front deck listening to the water fountains & closeness to nature. Only the mountains, ponds, woods & lake on your side and in front of you. And yet, only 2 blocks from busy Route 100 attractions. Spacious 1200 sq. ft. 4 prs. snowshoes winter, 2 kayaks, & a canoe on the 6 1/2 mile Reservoir. Hiking & fishing summer & winter. "Memories Are Made Here."

Guest favorite

Townhouse in Stowe

4.89 out of 5 average rating, 161 reviews

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

This beautiful Resort Condo is located in the award-winning, Top Notch Resort & Spa. Our spacious 2-bedroom, 2-bathroom condo is only 1 mile away from Stowe Mt. Resort while offering privacy and room to spread out on the resort’s 120 acres. It is perfect for families or couples. We are proud of our stellar reviews and competitive pricing. Newly updated, our home is ready for your perfect vacation! Enhanced Cleaning protocols in place!

Superhost

Home in Stowe

4.82 out of 5 average rating, 154 reviews

Great For Large Groups with Hot Tub

This property is not suited to noisy groups - please don’t book for partying. Recently renovated to meet every vacation need, this unique property has everything you require for a great trip. The property is huge, ideally located right on Mountain Rd - minutes to slopes, spas, breweries, restaurants, hiking, biking and swimming holes. With 4 large comfortable bedrooms, fun basement, huge living space with fireplace and private hot tub.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Charleston vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

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 vacation rentals in Charleston

Guest favorite

Chalet in Sutton

4.92 out of 5 average rating, 244 reviews

Cabin Sutton 264 - Relaxation en pleine nature !

Guest favorite

Home in Stowe

4.94 out of 5 average rating, 66 reviews

Charming and quiet rental for family or friends

Guest favorite

Home in Stowe

4.97 out of 5 average rating, 114 reviews

Cozy Mountain Home w/Million $ View

Guest favorite

Home in Stowe

4.98 out of 5 average rating, 155 reviews

Spacious Eco-Friendly Stowe Home for Family Fun

Superhost

Villa in Stowe

4.82 out of 5 average rating, 45 reviews

Beautiful 5 Bedroom Villa with Amazing Views

Guest favorite

Home in Westmore

4.92 out of 5 average rating, 60 reviews

New Vacation Home w/Awesome View!

Superhost

Home in Derby

4.81 out of 5 average rating, 43 reviews

Lake Salem House

Guest favorite

Vacation home in Stowe

4.95 out of 5 average rating, 22 reviews

Great location! Spacious 3 Bedroom, 2 bath unit.

Show all

Quick stats about vacation 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

Frequently Asked Questions

  • Do cabin rentals in Charleston have a kitchen?

    Absolutely! We offer over 10 cabin rentals with a kitchen in Charleston. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in cottage rentals in Charleston?

    Experience the best of Charleston with our cottage rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Charleston have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Charleston. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Charleston?

    Charleston has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cabin Rentals in Charleston?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Charleston?

    Yes! Work meets play with ease at over 10 vacation rentals in Charleston featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Charleston?

    Four-legged friends are welcome in Charleston. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Do cabin rentals in Charleston have wifi?

    Absolutely! We offer over 10 cabin rentals with wifi in Charleston. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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