Pet-friendly holiday rentals in Brattleboro

Beautiful Artsy Studio w/Fireplace - Pet-Friendly!

Welcome to the Artsy Studio at Culbertson House, a unique studio apartment with historic charm in a beautiful setting. The place features a big, romantic stone fireplace, wooden floors and walls, tasteful, comfortable furnishings, plentiful art and tasteful, artsy decor, full kitchen, 55" TV, and a deliciously comfortable king-size bed, all in a private yet convenient location. Bring your fuzzy friends with you as we are always pet-friendly! Skiing and ice skating are only five minutes away!

Clark Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

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+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

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 goats and dogs, 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.

~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.

Frosted Willows

Your family will be close to everything at this sunny, centrally located home on the Whetstone Brook. Just 0.6 miles from downtown Brattleboro, you can walk to shops, cafés, galleries, and more. Nestled in a quiet neighborhood, the house offers a peaceful place to relax after a day of exploring. Listen to the brook from the backyard, enjoy local adventures, and settle into a space that feels like home—perfect for a weekend getaway or a longer Vermont stay.

Cottage

The "Rustic" cottage is furnished with a queen bed, sofa and dining table. There is a small deck with patio furniture, fire ring with wood supplied, and a gas barbecue. It can accommodate 2 people comfortably. Private with parking. Host in separate house. Wi Fi from Xfinity, but please note that it can be patchy. Roku TV WI FI connected to router.

Lilac Ridge Farm House

Lilac Ridge Farm House is an 1830's cape located on a venerable 3rd generation working organic dairy farm. A classic white farm house with porches on the front facing the farm yard and small fresh produce stand. The interior is ample, modern and minimalist. A soaking tub under a skylight make for a relaxing space to unwind in.

The Carriage Barn

Situated on a 1792 Vermont Farmstead, the original Carriage Barn is a renovated 2-bedroom cottage that embraces historic building details within a comfortable and colorful design aesthetic. Located just 10 minutes outside of Brattleboro, Vermont, 45min to Mt Snow, and ~1hr to Stratton, Okemo, Bromley, and Magic Mountain.