
Holiday houses in Wardsboro
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Top-rated holiday rentals in Wardsboro
Guests agree: these stays are highly rated for location, cleanliness and more.

Mountain side acres
10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Vermont Botanical Studio Apartment
This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

New Cabin in Jamaica
Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Rustic Cabin in foothills of Green Mountains
Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Sweet Vermont Tiny Home Get Away
Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Apple Blossom Cottage: A Tiny House
The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Charming studio in renovated 19th century church.
This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Cabin-7 min to Ski Stratton-Woodstove-Views-Dog OK
Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property, fire pit, hammock on porch, propane BBQ, picnic table, forest views. TV with VCR & videos, turntable & records, games, Satellite Internet & WiFi 20-100 mbps. Staircase to loft, gas heat, wood stove, pellet stove. Full kitchen. Easy to use, odorless composting toilet. Dog friendly.

Dog Friendly A-Frame Retreat near Hiking, Skiing
The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 4 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe
Popular amenities for Wardsboro holiday rentals
Other great holiday rentals in Wardsboro

The Castle

Mt Snow/Stratton Getaway-TESLA Charger

Goldfinch Cottage: Timber Frame on 5 Private Acres

The Eagles Nest - Private Apartment

Mountain house w/ large hot tub

Mountain Cabin with Barrel Sauna - Rustic+Modern

Mt Snow Château

FULLY renovated 1 bed/1 bath ski in-out condo!
When is the best time to visit Wardsboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $534 AUD | $589 AUD | $463 AUD | $352 AUD | $373 AUD | $343 AUD | $385 AUD | $373 AUD | $389 AUD | $385 AUD | $415 AUD | $536 AUD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Wardsboro?
Four-legged friends are welcome in Wardsboro. Choose from more than 40 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Wardsboro?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 50 homes with wifi, over 50 homes with free parking, over 50 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Wardsboro have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Wardsboro. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cabin rentals in Wardsboro?
Experience the best of Wardsboro 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 Wardsboro have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Wardsboro. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Wardsboro?
Yes! Work meets play with ease at over 40 vacation rentals in Wardsboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do chalet rentals in Wardsboro have wifi?
Absolutely! We offer over 10 chalet rentals with wifi in Wardsboro. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Wardsboro?
Wardsboro has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cabin rentals in Wardsboro have free parking?
Absolutely! We offer over 20 cabin rentals with free parking in Wardsboro. Enjoy a tailored experience with all the comforts you desire.
Are there Wardsboro vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Wardsboro, available on Airbnb. Make a splash and soak up the sun in style!
Quick stats about holiday rentals in Wardsboro

Total holiday rentals
Explore 90 holiday rentals in Wardsboro

Nightly prices starting at
Wardsboro holiday rentals start at $90 AUD per night before taxes and fees

Verified guest reviews
Over 4,770 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Wardsboro holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Wardsboro rentals

4.9 Average rating
Wardsboro stays are highly rated by guests—averaging 4.9 out of 5!
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- Cabin rentals Wardsboro
- House rentals Wardsboro
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Peebles Island State Park
- Hooper Golf Course
- Fox Run Golf Club
- Dorset Field Club
- Northern Cross Vineyard
- Willard Mountain
- National Museum of Racing and Hall of Fame




