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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.

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Guesthouse in Newark

4.9 out of 5 average rating, 647 reviews

Hilltop Guesthouse

Our guest house is a private detached studio apartment. Close to many local activities, including Kingdom Trails mountain biking, V.A.S.T. snowmobiling, Burke Mountain Resort and beautiful Lake Willoughby. The full kitchen includes a refrigerator/freezer, range with oven, toaster, coffee pot, silverware, glassware, and cookware. The bathroom has an upright shower, and full linens and towels are provided. We invite you to come stay with us and spend time seeing what Northern Vermont has to offer.

Treehouse in Newport

4.97 out of 5 average rating, 196 reviews

Secluded Luxury Treehouse - Hot Tub + Projector

Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

Rental unit in Newport

4.99 out of 5 average rating, 166 reviews

The House of the Setting Sun, Private Apartment

The House of the Setting Sun is a great place to rest, relax & re-energize. Located in a family friendly neighborhood, while still within walking distance to restaurants & close to downtown Newport. The apt has its own dedicated WiFi, easy for working remotely. Downstairs is a room with a ping pong/pool table. You will have your own deck, where you can sit & enjoy a cup of coffee to begin your day or unwind with a glass of wine as the sun sets. Hosts on site and ready to assist if needed.

Farm stay in Irasburg

4.95 out of 5 average rating, 115 reviews

Private suite on small farm

Relax in the bucolic Northeast Kingdom on a small peaceful homestead & native plant sanctuary. We endeavor to make the space a cozy haven for you as well. Those efforts include reducing our environmental impact. We strive to be as plastic-free & organic as possible. We also compost & recycle and request that you do the same. We clean with Blueland products to create a healthy & welcoming space for all. Though the road crew takes good care, please note that the road is unpaved. Thank you!

Cottage in Westfield

4.9 out of 5 average rating, 133 reviews

Historic Schoolhouse Minutes From Jay Peak

After a long day of hiking, biking, or skiing, come take a swing at our charming historical cottage. Dating back to the mid 1800s it was one of the first schoolhouses in the area, today it is filled with all the modern luxuries one would need. Our quaint porch is perfect for bird watching or leaf peeping. The inside includes high ceilings, a bedroom and a cozy loft- both with queen beds. French culture is only a 10 min drive away; Vermont culture is abound with maple syrup and warm locals.

Home in Irasburg

4.95 out of 5 average rating, 141 reviews

Lord’s Creek Private Haven

Take a break at this peaceful, private getaway. We are located on a quiet road just a mile from our small-town square. Only three quarters of an hour from three ski resorts, Jay Peak, Burke Mtn and Smugglers Notch, we’re the perfect place to stay for your skication. There’s also plenty of hiking and beautiful lakes (Memphremagog, Crystal and Willoughby) to explore close by. Craftsbury Outdoor Ctr, Creek Hill Barn and, snowmobile trails are nearby. We offer a full kitchen and coffee bar!

Home in Brownington

4.99 out of 5 average rating, 130 reviews

Davignon Farm, Northeast Kingdom, Brownington, VT

Located between Burke Mountain and Jay Peak three miles from Lake Willoughby provides activities year round. The light and views from this quintessential Vermont farmhouse will amaze you! The property extends into the woods beyond the fields and 263 acres await your exploration. Open kitchen, new bathrooms, den and living room provide spacious comfort in this rural setting. The perfect couples getaway with a great location to take advantage of all the Northeast Kingdom has to offer!

Home in US

4.92 out of 5 average rating, 224 reviews

Northeast Kingdom, VT Clyde River House

Clyde River Farm & Forest's secluded Northeast Kingdom river retreat, the Clyde River House provides stunning views, shoreline, numerous birds, including bald eagles, nesting osprey, blue herons, and a pair of loons. Canoes and kayaks available for your use. Hiking, biking, cross country, downhill skiing trails, and snowmobile trails are within a short hike or drive of the house. Check out the many seasons of the Clyde River House. There's sure to be a time for you to visit!

Guest suite in Newport

4.83 out of 5 average rating, 236 reviews

Lake View Studio

Cozy studio apartment with patio and yard that has a beautiful view of the international Lake Memphremagog. Dog & cat friendly. It is close to the Kingdom Trails, Burke Mountain, Jay Peak Resort and just a 10 minute drive to Canada (30 minutes to Magog, Quebec). Lots of opportunity for outdoor activities such as hiking, kayaking, mountain biking, fishing, sailing, skiing/snowboarding and more. Welcome to use the patio and fire pit (Please bring your own wood and buy local).

Cabin in Newport

4.98 out of 5 average rating, 310 reviews

Sugar Hill

Come and embrace the majestic beauty of Vermont from Sugar Hill, a quaint log cabin nestled on 24 acres of beautiful countryside. Enjoy the views of the Canadian mountains from the front porch with a cup of coffee or a glass of wine; or wander around the pasture or woods behind the cabin. Close to both Jay Peak and downtown Newport, you can enjoy all those locations have to offer, or simply relax. Please note that the stairs to the 2nd floor are steeper than usual.

Home in Irasburg

4.82 out of 5 average rating, 485 reviews

Eco friendly. Military discount available.

If you are looking for a serene location that is nestled in the woods off a quiet country road and yet only 1 mile from the town square with its locally owned grocery store and gas station, you’ve come to the right spot! We are centrally located between Burke Mtn and Jay Peak resort, both being 30 minutes away. We sit 1/4 mile from the VAST trail and are near several lakes and hiking trails. Also close by is the Craftsbury Outdoor Ctr, Creek Hill Barn and breweries.

Rental unit in Sutton

4.99 out of 5 average rating, 421 reviews

Spring Hill Farm, coffee & hot tub

Private apartment w/hot tub for 4 & abundant amenities. Kitchen stocked w/ basics for cooking. Access to back yard with grill, fire pit & pond stocked w/ trout (for feeding). Access to 1 mile +/- of scenic wooded trails & beaver pond w/ pedal boat. Close to Burke Mtn, VAST & Kingdom Trails. Hosts on site & available if needed. DISH, smart TV, movies & games. Internet & WiFi not always reliable due to rural area. NO PETS. Please don't ask.

Vacation rentals for every style

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Popular amenities for Charleston vacation rentals

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

Cabin in Brownington

5 out of 5 average rating, 14 reviews

Back Forty Acres

Cabin in Westmore

4.96 out of 5 average rating, 28 reviews

The Hamblett at Hinton Hill

Guest suite in Barnston-Ouest

5 out of 5 average rating, 33 reviews

Magical stay in the Eastern Townships

Home in Westmore

4.9 out of 5 average rating, 20 reviews

GET LOST in the NEK of Vermont!

Guesthouse in East Haven

4.97 out of 5 average rating, 76 reviews

Brookside Loft in East Haven

Home in Charleston

4.86 out of 5 average rating, 37 reviews

Echo Lake Respite

Barn in Derby

5 out of 5 average rating, 26 reviews

The Loft

Home in Morgan

4.96 out of 5 average rating, 26 reviews

Beautiful Cape with private lake access

Quick stats about vacation rentals in Charleston

Total rentals
80 properties
Total number of reviews
1.8K 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 house rentals in Charleston have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Charleston. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cabin rentals in Charleston?
Experience the best of Charleston with our cabin rentals, starting at about $80 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 Cottage Rentals in Charleston?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, 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