
Family-friendly vacation rentals in Mount Holly
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Top-rated family-friendly rentals in Mount Holly
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Newly renovated. Minutes to Slopes & Trails
Healdville Hideaway has 3 acres of rural charm located on the backside of Okemo Mountain. Charm is a plenty in this 1500 SF single story, newly renovated home with views of the mountain & fields full of wildlife. This modern country decorated home provides the perfect comfortable setting for single or multi family enjoyment. The fully functional kitchen is available for making a quick snack or a full meal. The back acreage is perfect for building a snowman or doing a little cross country skiing.

Secluded tiny house resort - DOG FRIENDLY
New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Mapleside Escape: Sugar/Ski house
Your Mapleside Rustic Retreat awaits! This gem is nestled amidst the picturesque landscapes of southern Vermont and only a 12 minute drive to Okemo/Jackson Gore, 35 minutes to Killington/Pico. If the season is right it offers the unique opportunity to see some pure VT maple syrup being made! Skiing, snowboarding, hiking and mountain biking trails await, making this spot an ideal base for year-round fun. Come explore nearby towns which offer charming shops, dining, and cultural experiences.

Stunning Okemo Views - 3BD 3BA on 10 Private Acres
Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

Moon Valley Country Retreat no clean fee pets yes
Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

All Season Lovely and Zen Okemo Mt Lodge Condo
Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

Sasquatch Theme! - Local to Lake George & Saratoga
“A cozy, woodsy retreat with a Bigfoot twist—fun, peaceful, and full of character.” A 10-acre farm with a cozy 10x20 cabin, one queen-sized bed, and one futon. • Proximity to Lake George, West Mountain, Gore Mountain, and Saratoga Springs • Amenities, including WIFI, TV, fire pit, BBQ grill, fridge, microwave, coffee maker, heat, and AC. • Camp has an outdoor handwashing station with running water provided by a hose, an outdoor heated shower, and a porta-potty for bathroom needs.

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. We are as close or as far away as you would like us to be with our house right next door.

Okemo Mountain Getaway for Families w/ Pool Access
Perched on Okemo mountain, this spacious condo is the perfect year-round escape for families and groups. With ski-in/ski-out access, a cozy wood-burning fireplace, and a private balcony, it's perfect for any season—whether you're carving the slopes, hiking scenic trails, or enjoying the vibrant fall colors. Take a dip in the seasonal shared pool or unwind in the hot tub. Featuring a fully equipped kitchen, BBQ grill, and all the comforts of home, it's the ideal mountain getaway!

Peaceful Ludlow Base 5 minutes to Okemo
Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

Private Cabin/PetsOK/Minutes to Okemo/AC/Fast Wifi
Enjoy the beauty of Vermont at our private cabin. Situated on acres of woods next to a small creek, the cabin is 15 minutes to Okemo Mountain, excellent hiking on the Appalachian Trail and scenic Vermont towns for dining and shopping. With a queen bed loft, a double bed bedroom and a pull out sofa, the cabin sleeps up to 4 people. The kitchen is nicely equipped and there is a charcoal grill outside. High speed fiber optic internet will keep you connected. Max 2 pets allowed.

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub
Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.
Popular amenities for Mount Holly family-friendly rentals
Family-friendly home rentals with a hot tub

The Owl’s Nest in Landgrove

Beautiful Timber Frame Retreat

Okemo Ski Chalet with Hot Tub

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Scandinavian design Chalet w/ private hiking trail

Winterplace - Steps away from Slopes

Special Retreat in Nature, Woodfired Tub

Spacious Renovated Barn Apt on 100 acres!
Family- and pet-friendly home rentals

Modern Okemo Smart Cabin - As Seen On DIY Channel

Okemo Vermont Getaway

The Cluck House

Cozy Contemporary Downtown Texaco

Glamping Cabin with Private Pond and Mountain View

Comfortable farmhouse with stunning views

Beautiful Guest House near Bromley, Magic, Okemo

My house is your house!
Family-friendly home rentals with a pool

"Mountain View" Rustic Cabin Retreat w/Fireplace

Renovated unit, prime location! Shuttle on/Ski off

Comfy ski in/out studio at base of Pico-Killington

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

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

One Bedroom Suite Near Okemo

Beautiful rustic woods and fields retreat.

Beautiful Spacious Condo at Killington Resort
Quick stats about vacation rentals that are family-friendly in Mount Holly
Total rentals
170 properties
Nightly prices starting at
€ 103 before taxes and fees
Total number of reviews
4.9K reviews
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
100 properties have a dedicated workspace
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- Rentals with a fire pit Mount Holly
- Rentals with a sauna Mount Holly
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- Rentals with pools Mount Holly
- Pet-friendly rentals Mount Holly
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- Rentals with a hot tub Mount Holly
- Family-friendly rentals Rutland County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Hildene, The Lincoln Family Home
- Lake George Expedition Park
- Dorset Field Club
- Hooper Golf Course
- Northern Cross Vineyard
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Brattleboro Ski Hill
- Montshire Museum of Science
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Ekwanok Country Club