Vacation rentals in Marlboro

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!

Hidden Forest Cabin: Kitchen, Deck, Babbling Brook

Welcome to the Meadowbrook cabin: a restorative hidden gem for couples, friends, families, artists, & remote workers to reconnect with nature & each other. ✳ 15% discount for bookings of 7 nights or more! ✨ Highlights ✨ ‣ 10 private acres with babbling brooks, little trails, a meadow & rustic garden ‣ Fully-equipped kitchen ‣ Large deck with variety of seating for dining, birdwatching, stargazing, or chilling ‣ 11 minute drive to Brattleboro’s Downtown shops, restaurants, cafes, & river swims

Carriage Barn - Marlboro

Our place is within easy reach of Mt Snow, Carinthia, Marlboro Music Festival, and the super sweet town of Brattleboro. The 2-level apartment is entirely private and self-contained. Bonus offerings include an abundance of fresh country air and proximity to miles of woods trails. It's ideal for couples, solo travelers, and it's pet-friendly too. A short walk through the woods brings you to a spring-fed lake that is quiet and pristine. Winter, spring, summer, fall. Each season has its own magic.

4BR home amongst Skiing/Hiking with Amazing views!

Relax w/ the whole family & friends at this sweet, bright, open cabin surrounded by hiking trails & lakes. Enjoy amazing views/explore our 33 acres of rolling VT hills & meadows. Conveniently located b/w Wilmington & Brattleboro, Mt Snow less than 20 min. Home will allow you to stargaze on back deck AND make a quick trip into town for dinner/shopping. Watch the sunset, & sip something cool on beautiful back deck. Framed in natural wood, every window looks to green, creating a sense of solitude.

Barnside Cottage at Fruition Farm

Welcome to the Barnside Cottage at Fruition Farm, a newly renovated retreat on 182 acres in southern Vermont. Just 24 minutes from Mount Snow, it offers comfort, privacy, river access, a full-length deck, and four-season beauty. Enjoy hiking, foliage, gardens, and peaceful views. Camp at your own private riverside campsite, complete with fire pit and picnic area. Owners are nearby for support, and up to two dogs are welcome. A cozy, stylish getaway designed for rest, connection, and adventure.

Beautiful timber-frame treehouse

The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.

In the Trees Above the Village

This new apartment is located near Wilmington's charming downtown, a mile from Lake Whitingham, and a short drive to Mount Snow. Perched above a garage, the bright apartment features corner windows framing hill views. Find two bedrooms with queen beds, a living room with a queen sleeper sofa, and a bathroom with a sun shower. The kitchen boasts granite countertops, an island, and a farmhouse sink. Relax in the cozy living room with Roku TV. Strong Wi-Fi allows those to work while at play.

Large home in scenic Marlboro

Blueberry Lodge was designed by renowned architect Piet Van Dijk with an open, modern plan that is conducive to entertaining and social gathering. The space can accommodate the needs of different family arrangements with four bedrooms and en suite bathrooms on the first floor, and a great room on the second floor with multiple living spaces. The lodge has been our family vacation home for 25 years. It is well-suited for relational, multi-generational gathering in a beautiful location.

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly a dog, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

Peaceful cabin close to skiing & Brattleboro

Country privacy close to the best of Southern VT! This spacious home is close to skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants. Open concept with fireplace, cook's kitchen, jet bathtub, gardens, winter hot tub off deck, and large patio and fire pit give the perfect vibes for your VT gathering. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat.

Wilmington. In Town Village Home

Beautifully renovated bright, 125 year old home in town. House thoroughly cleaned and sanitized after each stay. Touchless flushing toilets. Mini-Split air conditioning in each bedroom and on the main level. Minutes to MT Snow. Easy walk to town for food and shopping. Deerfield river directly across the street. 2 min from the lake. Valley hiking trails within sight. There is a 2 car limit. A request for additional vehicles needs to be made prior to check-in.

The Crooked Paw

Explore the southeast corner of Vermont, the hidden valleys and artistic culture by staying at the Crooked Paw, a centrally located getaway to your next Vermont adventure. A renovated carriage house built in 1905 with pasture views and a meandering brook, The Crooked Paw sits on a quiet dirt road, 20 mins to the cozy ski hamlet of Wilmington, and the art hub of Brattleboro, there's something for everyone. Bring your fur babies along for the ride!