Family-friendly vacation rentals in Brattleboro

Modern Spacious Home with Mountain Views

Modern Home in Brattleboro with mountain view & many extras: Italian-Marble master-suite, Jacuzzi/Shower for 2, walk-in closet, king bed, grill, heated garage, cable, WiFi. Open-concept living room w/ cathedral ceiling, office, & movie screen. Large open kitchen w/ wine fridge. Second bedroom w/ loft. Explore hiking trails from backyard. Pets ok! 3 mins from Vermont Country Deli & I91 Exit 2. Walking distance to dog park, swimming holes. Downtown: 4 mins Mount Snow: 40 mins Stratton: 54 mins

Forest Street Retreat Attached Guest House

Less than 1 mile from the Retreat Farm, this private & peaceful attached carriage house is perfectly located in the heart of Brattleboro. Only steps from the Retreat Woods nature trails & a short walk into historic downtown, you'll find coffee shops, bookstores & the Stone Church nearby. Thoughtfully designed to have a minimal cozy cabin feel, the downstairs is open concept living w/ a gas fireplace. Both bedrooms are upstairs. Outdoors, enjoy 10 miles of trails & the beautiful West River.

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Cozy Home for 2-5 People in Vermont

Comfortable house for 2 to 4 people (two queen-sized beds) and a pull-out couch for a 5th person and a self-inflatable bed. Located in a quiet neighborhood. There are two main bedrooms with queen beds in each. There is also a pull-out couch in the room with the fireplace though it is not as comfortable as the self-inflatable bed (and deflatable) in the house. Fast Wi-Fi from Xfinity. Easy to get into Brattleboro Center and an excellent location for exploring Southern Vermont.

Bright and Modern Chestnut Street Apartment

Enjoy a unique stay at this central, beautifully-remodeled apartment in quaint Brattleboro, Vermont. The apartment is attached to the back of the charming 1914 home where I live, and has a private, separate entrance so guests can come or go as they please. This carefully-curated apartment includes tasteful decor, a well-appointed kitchenette, organic cotton sheets, and natural bath products. Just off Hwy 91, the apartment is located in the quiet, historic neighborhood of Esteyville.

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.

~Serene Barn Retreat~

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

Spacious Brattleboro home on river, walk to town

Spacious 3,000 sq. ft. home with 4 bedrooms (3 queens, 2 twins) and 4 bathrooms, 3 en-suite. Enjoy a formal living room with grand and upright pianos, a cozy TV room, and a fully equipped kitchen with eat-in area leading to a deck with stunning river and mountain views. Formal dining seats 12. Expansive grounds are perfect for relaxing or hosting special events. Just a 10-min walk to Brattleboro’s Main Street shops, cafes, and culture.

Guest House @ 120

Unforgettable designer stay in the heart of downtown Brattleboro. Curated art, luxe finishes, and boutique comfort set this experience apart. Walk to the best cafes, boutiques, and galleries. Enjoy a chef’s kitchen, plush bed, quaint bath, and fast Wi-Fi. Every detail is elevated, every corner styled. Steps from Amtrak, wrapped in Vermont charm. Perfect for escapes, retreats, or inspired work. You won’t want to leave.