Vacation rentals with breakfast in Windham County

Find and book unique breakfast rentals on Airbnb

Top-rated breakfast rentals in Windham County

Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.

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Superhost

The open living area features a spacious gray sectional sofa arranged around a modern coffee table. A stone fireplace is the focal point, with a flat-screen TV mounted above it. Large windows offer views of the surrounding trees, enhancing the natural ambiance.

Home in Winhall

4.74 out of 5 average rating, 35 reviews

Summer Retreat: 5BD Getaway, Hot Tub, Pond, & BBQ

Welcome to the newly renovated modern 5BD/4.5BA mountain getaway only 7 min away from Stratton Ski Resort, offering a perfect escape for large groups. Whether you are returning from an active day and want to enjoy a relaxing hot tub experience or simply enjoy a dreamy natural ambiance, this place is able to meet all your expectations. ✔ 5 Comfortable Bedrooms ✔ Open Design w/ Fireplace ✔ Hot Tub ✔ Desks & Monitor ✔ Outdoors (Deck, BBQ, Private Pond) ✔ Smart TVs ✔ Fast Wi-Fi ✔ Garage & EV Charger

Top guest favorite

A large arched window offers a view of the mountains and a warm sunset glow. A small round table is positioned nearby, adorned with a floral arrangement and magazines. A textured chair adds a cozy touch to the space.

Home in West Brattleboro

4.93 out of 5 average rating, 116 reviews

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

Guest favorite

Two red Adirondack chairs are positioned around a small table on a wooden deck, surrounded by lush green trees. Natural light filters through the foliage, creating a serene outdoor space that invites relaxation.

Chalet in Jamaica

4.89 out of 5 average rating, 19 reviews

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.

Guest favorite

A covered porch features wooden flooring and a woven loveseat, inviting relaxation. Nearby, a door leads into the cottage, with a small mat at its base. Lush greenery surrounds the area, showcasing the serene landscape just beyond the railing.

Cabin in Guilford

4.97 out of 5 average rating, 61 reviews

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

Superhost

A fire pit area is surrounded by six green Adirondack chairs, set within a natural landscape of fallen leaves and trees. In the background, a spacious two-story home features expansive glass windows and a large deck, providing a welcoming outdoor space.

Home in Jamaica

4.93 out of 5 average rating, 15 reviews

The Mountain Escape

Welcome to Stratton Mountain Escape! This spacious 4-bedroom, 3.5-bathroom + loft home is the perfect retreat for families and groups. Enjoy an open-concept kitchen and living room, a luxurious master suite with a jacuzzi tub, or the spacious loft that overlooks the living room. Relax in the huge outdoor hot tub, gather around the fire pit, or unwind on the large deck. Just minutes from Stratton Mountain, this is the ultimate getaway for skiing, hiking, and relaxation. Book your stay today!

Top guest favorite

A private deck is equipped with a wooden table and two wicker chairs, positioned on a wooden surface. Lush greenery surrounds the area, providing a peaceful outdoor space for relaxation.

Apartment in Brattleboro

4.98 out of 5 average rating, 132 reviews

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 .

Top guest favorite

A warm wood interior of the studio features an open layout with a living area, kitchenette, and sleeping area. Large glass doors allow natural light to fill the space, while views of greenery are visible outside. A cozy seating area and wooden bench complete the inviting atmosphere.

Barn in Marlboro Township

4.96 out of 5 average rating, 312 reviews

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.

Guest favorite

A charming barn exterior is adorned with rustic wooden siding and features a striking red door framed by flowering gardens. Lush greenery and colorful blooms enhance the entrance, leading to the inviting space within.

Apartment in Dummerston

4.92 out of 5 average rating, 403 reviews

~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.

Top guest favorite

An open-concept living area features rustic wooden beams overhead and a cozy stone fireplace. A spacious dining table is surrounded by modern chairs, while the kitchen showcases vibrant green cabinetry and sleek appliances. Large windows allow natural light to flood the space.

Home in Winhall

5 out of 5 average rating, 17 reviews

Summer in Winhall - Fire-pit, Hot Tub, Sleeps 10

3 Bedroom, 3 Bathroom Sleeps 10 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

Top guest favorite

Townhouse in Dover

4.98 out of 5 average rating, 58 reviews

Serene VT Escape. Lakes, Trails, Golf and peace

Enjoy the charm of Vermont in our townhouse. All the beauty, serenity and fun of Vermont is right outside our door! Miles of beautiful Green Mountain Forest trails await through trailhead a short walk away. Hiking, watersports, horseback riding, golf, antiquing, or just relaxing... the choice is yours. A delightful smorgasbord of shops and restaurants await only a few mins away. A romantic escape, a family adventure, a restful retreated the Lemondrop lodge is for you.

Top guest favorite

Cabin in Winhall

4.96 out of 5 average rating, 345 reviews

A-Frame Mountain Retreat near Manchester

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 6 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

Top guest favorite

Condo in Dover

4.99 out of 5 average rating, 121 reviews

March Ski Escape! Mt. Snow Condo w/ All the Perks

Welcome to Vermondo Mount Snow! This cozy 1-bedroom, 1.5-bathroom ski condo at the base of Mount Snow ski resort comfortably accommodates 6 guests. The condo boasts a fully stocked kitchen, cozy fireplace, spacious deck, convenient office space, a separate bedroom and access to an amenity center which has an outdoor pool, hot tub, sauna and gym. Perfect for short or long term stays.

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What guests are saying

Betty's Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

5 out of 5 average rating, 5 reviews52 months ago

This is a lovely place and space! Cozy, comfortable, clean and simple style, Charlie & Megan go the extra mile to make sure your stay is comfortable and you have everything you need. They communicate before and during your trip and help with anything you need. They are COVID conscious and we felt very comfortable and safe with the measures they put in place. Oh, and the breakfast menu is delicious and they have an amazing cocktail list perfect for winding down at the end of the day.

Private room in Wilmington

What guests are saying

Moose House: located 5 minutes to Mt. Snow

4.89 out of 5 average rating, 91 reviews2 months ago

Great place for a large family or group of friends to have a ski vacation. Cozy, plenty of games and TV’s. Close to mountain, 5 min drive, but there’s also the option to take the (free) Moover bus (6 min walk). Market at the end of the street has everything you need. Would stay again.

Chalet in Dover

What guests are saying

Farm at Williams River House - Hawthorne Suite-ADA

5 out of 5 average rating, 21 reviews2 months ago

We had a wonderful stay at John and Kathy’s farmhouse! Great location for a peaceful retreat and close to several mountains for skiing. John’s breakfast was a fantastic start to each day. They were extremely knowledgeable and helpful regarding things to do in the area. We hope to be back again!

Private room in Chester

What guests are saying

Grey Lady Suite @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

5 out of 5 average rating, 5 reviews38 months ago

EVERYTHING we hoped for and MORE! Charlie and Megan's property is wonderfully located, the room was spacious, clean and well thought out. The common area on the first floor was welcoming, warm and had multiple spaces whether you wanted to sit by the fire or enjoy a beverage at the bar. And, we had no idea that the breakfast would be so tasty and filling. And, not to mention eggs from their own chickens!! Charlie and Megan are wonderful hosts and we can't wait to come back for our next ski trip (just 15 minutes from Mt Snow!!!).

Private room in Wilmington

What guests are saying

Wilmington Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

5 out of 5 average rating, 3 reviews1 week ago

I can’t say enough good things about this place. From the moment we arrived, everything exceeded expectations. The inn was spotless, beautifully decorated, and had every amenity we could have needed—and then some. The bed was super comfortable, the view was stunning, and every little detail was clearly thought out with care. The host was incredibly warm, responsive, and welcoming. They went above and beyond to make our stay special, offering great local recommendations and making us feel truly at home. We’ve stayed at a number of places, but this one stands out as one of the best. If you’re considering booking—do it! You won’t regret it. We’re already planning our return trip.

Private room in Wilmington