
Family-friendly holiday rentals in Andover
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Top-rated family-friendly rentals in Andover
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Fat Cat Barn - Close Okemo & Magic, Vermont
Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Glamping Cabin with Private Pond and Mountain View
This little glamping cabin with cozy woodstove is set at the far edge of a field overlooking a wildlife pond, seasonal fountain, and mountain. It is a peaceful place, surrounded by beauty, and special not just for these amenities but because it is improbably located on four private acres right in Manchester Center. The property abuts 70 acres of preserved land, but is steps from Main Street and all the shopping, dining, and outdoor options that this lovely year-round tourist town has to offer.

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.

Monadnock Sunrise Forest Hideaway
Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

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.

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

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.

Lovely 1-Bedroom condo with indoor fireplace!
This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, restaurants and bars. "Eight Oh Brew" tap house is located on the base floor of the building. This location has free onsite parking, free firewood and coin laundry machines.

Beautiful 2 Bedrooms in Mountains w/ full kitchen
Ready for a Vermont getaway? In heart of ski area w/ A+restaurants & charming villages are two cozy bedrooms on 2nd fl of larger apt complex. Each bedroom has separate toilet/sink room, shared shower room for your and your guests alone. Hallway living room at one end with 2 couches, desk and TV Other end is full compact kitchen with dishwasher, stove and over, full size refrigerator, coffee maker and microwave.

Private Hilltop farm apartment
Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Apartment on Main Street
One bedroom apartment with kitchenette (mini-fridge, coffee maker, microwave, dishes etc.), full bathroom with laundry, and open living space. I am an English teacher, so there are lots of books! Apartment is located in the Village of Saxtons River- within easy walking distance from the Market, Vermont Academy, our new Park, and Main Street Arts.
Popular amenities for Andover family-friendly rentals
Family-friendly home rentals with a hot tub

River House Apartment - Dog friendly

The Owl’s Nest in Landgrove

Beautiful Timber Frame Retreat

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Vermont Retreat Luxe Yurt, Romantic & in Nature

Mountain side acres

Vermont Getaway Apartment

Newly renovated private space on Ascutney Trails
Family- and pet-friendly home rentals

Rustic Cabin in foothills of Green Mountains

Cabin on the Hill

The Cozy Little Red Cabin

Love Shack Yurt on Star Lake (100% off grid)

Mapleside Escape: Sugar/Ski house

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK

Private Modern Cabin w/View of Fields, Hills

Serene Bus Getaway Among Rolling Farm Land
Family-friendly home rentals with a pool

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Winter Dream! The Handle Lodge at Snowtree Condos

Winterplace - Steps away from Slopes

Beautiful Spacious Condo at Killington Resort

Beautiful rustic woods and fields retreat.

Cozy Vermont Antique Sugar House with Fireplace

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace

On Pico Great times 1 nite Ok 1 bedrom Ski in out
Quick stats about holiday rentals that are family-friendly in Andover

Total holiday rentals
Explore 40 holiday rentals in Andover

Nightly prices starting at
Andover holiday rentals start at $328 NZD per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Andover holiday rentals include Wi-Fi access

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

4.9 Average rating
Andover stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Rentals with outdoor seating Andover
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- Family-friendly rentals Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Crotched Mountain Ski and Ride
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Dorset Field Club
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- The Shattuck Golf Club
- Willard Mountain
- Northern Cross Vineyard
- Brattleboro Ski Hill
- Autumn Mountain Winery




