
House holiday rentals in Andover
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Top-rated house rentals in Andover
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Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!
4.95 out of 5 average rating, 324 reviews
Updated 6BR Home 4 min to Okemo w fenced in yard!
Fully renovated! This single-family home is a perfect getaway for you and your friends or family to enjoy some of the best terrain in the Northeast at Okemo Mountain, located just 5 minutes away. After a day on the slopes come home, unwind and relax or head to downtown Ludlow area to enjoy restaurants, bars, shopping and more. Pet-friendly, large fenced in yard. Nearby attractions: - Camp Plymouth State Park & Echo Lake - Fox Run Golf - Buttermilk Falls hiking and swimming - Killington Skiing!
4.93 out of 5 average rating, 101 reviews
Luxury Mid-Century Modern Vermont Home, Okemo View
The Brewster House is a premiere destination for skiing, hiking, enjoying the country or just lounging by the pool. Designed by renowned mid-century modern architect turned painter George W.W. Brewster, the Brewster House has been lovingly restored and updated, and filled with original, local art. With gorgeous views of Okemo and Hawks Mountain Wildlife Area, the Brewster House is close to incredible dining, great art galleries, and antique shops. Come bask in beauty and relax completely!
4.99 out of 5 average rating, 101 reviews
Ski Chalet with Hot Tub on Okemo Mountain
Escape to this spacious 3-level, 1,700+ sq. ft. ski chalet, just 4 minutes from Okemo Mtn Resort and downtown Ludlow, 6 minutes from Jackson Gore, and 30 minutes from Killington. Floor-to-ceiling windows frame beautiful 180-degree views of the wooded backyard, creating a peaceful mountain retreat. After skiing, hiking, or exploring, unwind by the fireplace or soak in the private Jacuzzi hot tub. With plenty of space and a fantastic location, this chalet is an ideal Vermont getaway year-round.
4.97 out of 5 average rating, 184 reviews
Private, Large 4BR home | Pet friendly | 10 Acres
Okemo & Killington Ski House Large 4 bedroom 2.5 bath, 3,000+ sq ft home located close to Okemo Ski Resort and surrounded by 10 acres of land at the end of a private road! This recently renovated home features 3 levels, a large game room, 5 separate sleeping areas and a large covered porch! Enjoy ultimate privacy with proximity to multiple outdoor adventures including skiing, golfing, hiking and mountain biking. Just a short drive to downtown Ludlow and other surrounding stores in Cavendish.
4.93 out of 5 average rating, 103 reviews
Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat
4.95 out of 5 average rating, 363 reviews
Vermont 1828 Reunion House, near Okemo
The Vermont 1828 Reunion House, close to Okemo is a spacious historic vintage ski lodge and farmhouse with 2 kitchens, 8 bedrooms, 4 baths, & a quintessential Vermont character. Excellent for gatherings & family reunions. Linens & towels provided, beds made. 10 acres, meadow & hidden pond. . A new automatic sprinkler system was installed in 2024 & the house complies with all safety regulations & certified by the town of Chester. Must be 25 years to rent. Long term rentals possible.
4.8 out of 5 average rating, 101 reviews
Charming Chester Farmhouse Near VT Slopes
Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!
4.85 out of 5 average rating, 108 reviews
Cow Barn Lodge
Our home is located in MT. Tabor, Vermont, just off of Route 7, in a country setting with beautiful Mountain views of the Green Mountain National Forest, Dorset and Danby Mountains. The house is an old barn converted into a beautiful spacious home, on 4 acres. Snowmobiling from our place, plus 4 major ski areas less than 30 miles away. Hiking, fishing, swimming, golfing, and the Equestrian horse show are all nearby. as well as shopping in nearby Manchester and Rutland Vermont.
4.98 out of 5 average rating, 295 reviews
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
Ideal to host up to 6 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of nature. Chester and Ludlow, VT are minutes away and call you to explore historic landmarks and enjoy skiing at Okemo Mountain (located 15 minutes away). With modern facilities & a private location, this will be your home away from home! New in June 2024 - we added a large outdoor patio equipped with a Jacuzzi Hot Tub, Fire Pit, and picnic table.
4.96 out of 5 average rating, 100 reviews
Modern 3-bedroom A-frame in Londonderry w/ Pond
This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min). STR License 26-23-185
4.99 out of 5 average rating, 155 reviews
Stunning mid-century house on 2.5 private acres
Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4wd or awd vehicle is recommended. Important note: The grill is put in storage and not accessible November-April due to inclement weather. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. The house has a non-working fireplace.
4.98 out of 5 average rating, 433 reviewsPopular amenities for house rentals in Andover
House rentals with a pool

Classic VT Ski Chalet - Walkable to Okemo Ski Lift
4.92 out of 5 average rating, 114 reviews
Ski Mountain View Estate
4.96 out of 5 average rating, 142 reviews
Beautiful Bromley/Manchester VT Retreat w/hot tub
4.9 out of 5 average rating, 184 reviews
Family-friendly 4BR | Pools Hot Tub | Near Mt Snow
4.89 out of 5 average rating, 183 reviews
Historic Farm Stay | Heated Pool + Hot Tub
4.98 out of 5 average rating, 214 reviews
The Brick House on Washington Street
4.93 out of 5 average rating, 251 reviews
SugarBear- Pool, AC, Sauna, Gym, Tennis!
4.99 out of 5 average rating, 169 reviews
Luxury Condo Tucked in the Heart of Killington
4.86 out of 5 average rating, 260 reviewsWeekly house rentals

Artistic Southern Vt Countryside Home at Windham
4.96 out of 5 average rating, 102 reviews
Cape Cod Home in Woodstock, Pet-Friendly & Wooded
4.99 out of 5 average rating, 170 reviews
Vermont Mirror House
4.95 out of 5 average rating, 161 reviews
Stunning Okemo Views - 3BD 3BA on 10 Private Acres
4.99 out of 5 average rating, 142 reviews
Modern Cabin ~ 3min to Stratton Resort
4.92 out of 5 average rating, 147 reviews
Luxury VT Retreat. Breathtaking Views & Sunsets
5.0 out of 5 average rating, 82 reviews
Mountain Retreat | 9 Acres | Views | Hot Tub
5.0 out of 5 average rating, 31 reviews
Sunrise Haven Hot Tub + Fireplace Near 4 Ski Areas
4.92 out of 5 average rating, 13 reviewsPrivate house rentals

Cozy 2 bedroom house, close to Okemo & Killington
4.98 out of 5 average rating, 62 reviews
6 Bed 6 Bath | Hot Tub | Arcade | 16 min Okemo
4.78 out of 5 average rating, 46 reviews
Modern cabin close to all mountains
5.0 out of 5 average rating, 25 reviews
Pettengill Schoolhaus scenic 2 min to main village
4.84 out of 5 average rating, 25 reviews
The Evergreen Chal-A
5.0 out of 5 average rating, 47 reviews
Just an Incredible Vermont Mountain Retreat
4.9 out of 5 average rating, 20 reviews
Sauna Retreat • Fire Pit Nights • Close to Okemo
5.0 out of 5 average rating, 58 reviews
Charming New England Cape
4.95 out of 5 average rating, 99 reviewsDestinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Dartmouth College
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Killington Resort
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Montshire Museum of Science
- Camp Plymouth State Park
- Quechee Gorge
- Jamaica State Park
- Bridge of Flowers
- Crotched Mountain Ski and Ride
- Willard Mountain





