Holiday rentals with breakfast in Windham County

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

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

Cook, eat, ski, hike and be merry!

A cook’s and family’s perfect getaway in beautiful Southern Vermont! We love to cook - and if you do too you’ll love cooking in this open floor plan while friends play games or read in front of the fire. In addition to fully stocked pots and pans you’ll find high-end cutlery, cast iron skillets, a paella pan, slow cooker, waffle iron, blender a Webber BBQ, Nespresso machine, French press and drip coffee maker, along with all of the utensils, spices and herbs needed for a gourmet meal.

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 .

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.

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

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.