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

Value · Location · Pets

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.

Location · Family · Hiking

Chalet /Stratton Mountain VT /Tesla Charger/5 bdrm

Ski Chalet w/Tesla Charging! A quick 5-minute drive to Stratton Base, offering captivating views of Stratton Mountain on 8.82 acres of tranquil countryside. 5 bedrooms, 3 baths spread across multiple levels. The lower level unit is a versatile in-law setup or separate space for kids, while the wrap-around deck welcomes you to fully immerse yourself in nature. A detached 2-car garage with a Tesla Wall Charger. Don't miss this exceptional opportunity to make this prime location your next vacation!

Family · Location · Indoor spaces

Experience Vermont's Fall Magic at the Lemondrop

Wake up minutes from Mount Snow at The Lemondrop Lodge, a whimsical 3BR/3BA mountain townhouse made for hiking weekends, golf getaways, lake days, and summer family trips, wedding trips. Spend the day exploring nearby trails, biking the mountain, playing a round at Mount Snow Golf Club, or swimming, paddling, and boating at Harriman Reservoir. Then come home to grill on the private deck, relax by the fireplace, unwind in the indoor heated pool, or settle in with foosball, Xbox, and board games.

Location · Value · Layout

Stratton Mountain Chalet | Hot Tub, Game Room & EV

Escape to this spacious Stratton ski chalet, just 7 mins from Stratton Mountain Resort and mins from Bromley Mountain and Manchester. This family-friendly mountain retreat which sleeps up to 16 guests, is the perfect vacation rental for ski trips, family reunions, large group getaways, workcations, and year-round adventures. Whether you're planning a winter ski vacation, a spring hiking trip, a summer retreat, or a fall getaway, this all-season home is perfectly located for exploring Vermont.

Value · Location · Comfort

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

Value · Location · Checkout

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.

Location · Family · Heating

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 .

Location · Value · Beach

~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.

Value · Location · Outdoor spaces

Fall Escape - Winhall - Fire-pit, Hot Tub

3 Bedroom, 3 Bathroom 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

Location · Family · Accuracy

Chalet Lopez

Welcome to Chalet Lopez, your cozy getaway in Wilmington, Vermont. Enjoy fast WiFi, a fully equipped kitchen, comfy living spaces with propane heat, and a beautiful fireplace ready for you to relax by. You will be close to Mount Snow, hiking trails, lakes, golf, great restaurants, and local bars. House rules are simple: no pets, no smoking, no parties, quiet hours at 9pm, and please keep food out of bedrooms. Checkout is easy and quick.

Location · Family · Indoor spaces

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.

Family · Location · Checkout