Family-friendly vacation rentals in Whitingham

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!

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

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!

Sasquatch Theme! - Local to Lake George & Saratoga

“A cozy, woodsy retreat with a Bigfoot twist.” Tenting is allowed for additional guests. 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.

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 tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

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!

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.

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.