
Family-friendly vacation rentals in Whitingham
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Whitingham
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Refined, serene and like no other, Marlboro, VT.
Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Mount Snow Yurt is a one-of-a-kind luxury getaway nestled in the tranquil serenity of Vermont’s mountains, just 7 minutes from the Mount Snow Ski Resort, an Epic Pass destination. This magnificent pet-friendly yurt is surrounded by the captivating scenery of Mount Snow and is located near a beautiful creek, providing an even more peaceful and serene atmosphere. Furnished with modern amenities, including a luxurious private sauna, this yurt offers everything you need for a relaxing stay in nature

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

The House of Pi
Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Vermont lake house near Mt. Snow-fab 360 views!
Welcome to our fabulous farmhouse on 3 green acres! Enjoy amazing views of Lake Sadawga and the surrounding Green Mountains as you kick back in our cozy stylishly furnished home. The house comfortably sleeps 8+ with 4 bedrooms, 2 full bathrooms, and a finished loft space. We are located off the beaten path on a paved road with multi-car parking. This wonderful year-round retreat is a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!
Tucked away in the bends of Burrington Hill Road, you’ll find our family’s Whitingham Wonderland, where our Irish touch is sure to make you feel at home and our NYC energy will keep you entertained. Our home is stocked with games for all ages as well as multiple Smart TVs, a fire pit and grill. To enjoy all Vermont has to offer we are only 30 minutes from Mt Snow and 45 from Stratton with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!

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, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

The Hideaway Camp
The Hideaway Camp is a very private cabin on a 100 acre property. There are hiking/x country ski trails on the property and close access to the VAST trails. A scenic 20 acre pond for kayack and canoeing and a brook with a rustic cocktail deck overlooking it. the Jacksonville General store is 2 minutes away and it is warm and friendly with all the groceries you might need. The cabin is well stocked for cooking and with high speed internet you can WFH or stream favorite shows.

Schoolhouse Spa Retreat on a Vermont Farm
Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Log Cabin: Amazing Views, River Frontage, Hot Tub
A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.
Popular amenities for Whitingham family-friendly rentals
Family-friendly home rentals with a hot tub

The Birchwood Cabin - Stunning Mountain Views

Secluded Farmhouse Retreat - stunning views

Boutique TINY home+private HOT TUB-walk to Main St

Serene & Stylish Chalet w/ HOT TUB near Manchester

Private Mountain Lodge-views, privacy, hot tub

Mountain side acres

A frame cabin with Hot tub near Stratton, VT

Mountain view chalet with hot tub & fire pit!
Family- and pet-friendly home rentals

Shakespeare’s Folly Side Farm and AirBnB.

~Serene Barn Retreat~

**Happy Hour! Gorgeous & Modern Downtown Retreat**

The Vermont Farmhouse|Hiking|Dog Trails|Village

Classic Vermont A-Frame | Fire Pit | Near Stratton

Log Cabin King Beds AC Near Hike Bike Swim Golf!

Apple Blossom Cottage: A Tiny House

Cozy Vermont Antique Sugar House with Fireplace
Family-friendly home rentals with a pool

Bear's Den - Mt Snow Townhome w/ Heated Pool!

The 1770 House

The Brick House on Washington Street

Cozy cottage with pool, walking distance to lake

Beautiful rustic woods and fields retreat.

Cozy Cottage with pool and walk to lake

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace

Silver Brook Cabin
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Pet-friendly rentals Whitingham
- Rentals with a fire pit Whitingham
- House rentals Whitingham
- Rentals with a fireplace Whitingham
- Rentals with outdoor seating Whitingham
- Rentals with a washer and dryer Whitingham
- Rentals with a patio Whitingham
- Family-friendly rentals Windham County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- June Farms
- Fox Run Golf Club
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Naumkeag
- Norman Rockwell Museum
- National Museum of Racing and Hall of Fame
- Berkshire Botanical Garden
- New York State Museum
- Emerald Lake State Park
- Hancock Shaker Village
- Rensselaer Polytechnic Institute





