Holiday rentals with breakfast in Windham County

Plush Vermont ski + summer chalet in a great spot

When you stumble on Jamaica Vermont, during the crisp sun-filled summer swimming season, you'll find yourself promptly making plans to come back for ski season too! Whatever the season our place is a centrally located and easy to love 3 bedroom, 2 bath chalet. The house has been substantially renovated with new appliances, fresh furniture and modern tech, yet it still features your favorite old school amenities: fire pit and wood stove, deck, board games, heated mud room and a warm snuggly vibe.

Guilford Grove Cottage

Guilford Grove Cottage is a simple, comfortable small cottage on the threshold of the forest. A quiet and clean refuge with everything you need to relax in scenic southern Vermont. Prepare meals in the kitchen (breakfast supplies provided), relax on the loveseat, chill on the covered porch and enjoy being on the edge of nature; shoe-free and free from chemicals and artificial fragrances. Brand new construction. Easy access from I-91 & Route 2, 15 mins from Brattleboro and 20 to Greenfield, MA

Idyllic getaway with wrap-around deck

This one-of-a-kind accommodation was featured on Animal Planet’s Treehouse Masters! It offers a sizable sleeping loft with queen bed, living area, wrap around deck, bath with enclosed shower, and a kitchenette with mini-fridge, microwave, sink and dish-ware. It overlooks a gorgeous pond and is located in a village setting that can't be beat--enjoy the Rock River, hike in the Green Mountain National Forest, visit the nearby covered bridge, ski at Mount Snow, and do city things in Brattleboro.

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

~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.

Summer in Winhall - Fire-pit, Hot Tub, Sleeps 8

3 Bedroom, 3 Bathroom Sleeps 8 Hot Tub, Fire Pit - 5 minutes from Bromley Mountain - 8 minutes from Stratton Mountain - 15 minute drive to Manchester Bedroom Highlights: - Primary Bedroom: King bed with en-suite bathroom - Second Bedroom: Ideal for families, featuring twin and full bunk beds - Third Bedroom: Queen bed with en-suite bathroom Outdoor Amenities: - Relax in the private hot tub under the stars - Gather around the cozy firepit for evening conversations

Cozy Log Cabin - Dog Friendly

Escape to a one-of-a-kind log cabin that caters to every member of your family. Welcome to our exceptional 3 bedroom, 2 bathroom log cabin in the mountains. From the moment you step through the door, you'll be enveloped in an atmosphere that combines rustic charm with modern convenience, ensuring an unforgettable short-term rental experience for the whole family.

Stratton Mountain Getaway: Hot Tub, Firepit & Pond

Welcome to your perfect Vermont getaway! This spacious 5BR/4BA chalet in Strattonwald is just minutes from Stratton Mountain Resort, Bromley’s slopes, Manchester’s shops and dining, and scenic hikes. Whether you’re building snowmen with the kids, cozying up by the fire, or soaking in the hot tub with pond views, this home balances adventure and relaxation.

Apartment on Main Street

One bedroom apartment with kitchenette (mini-fridge, coffee maker, microwave, dishes etc.), full bathroom with laundry, and open living space. I am an English teacher, so there are lots of books! Apartment is located in the Village of Saxtons River- within easy walking distance from the Market, Vermont Academy, our new Park, and Main Street Arts.