
Holiday rentals with breakfast in Windham County
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Top-rated rentals with breakfast in Windham County
Guests agree: these breakfast rentals are highly rated for location, cleanliness and more.
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Popular amenities for rentals with breakfast in Windham County
House rentals with breakfast

Cook, eat, ski, hike and be merry!
We had a wonderful week at Mathew and Greta's home. Perfect ski week. Beautiful views, light, and surroundings. The home was perfect for our group of 8 with two families sharing (one on the top floor and one on the bottom) gave each family privacy, a bathroom and space to get our stuff out of the common area. Fully stocked with anything that we needed. Thank you! I'd love to book again. :)

Cozy Room in Brattleboro
Nice location and easy to find! Jess was a great host!

Historic Farmstead - Private 2 BR Guest Suite
Cozy and comfy, we had a great time staying at Emily's for the weekend. Highly recommend!

Peaceful Room in Brattleboro
Jessica is so lovely and welcoming. Her pets are adorable and well behaved. The room was clean and cute. The only negative for me (I'm not a cat owner) was the smell of the litter box.

Peaceful country homestay overlooking pond
I had a wonderful stay at Megan's home! Her home was exactly as described, and her presence was both nurturing and respectful of privacy. Home is quaint, picturesque Vermont country style, modern and charming. Location was an easy hop to Putney and the Putney School, where my son attends. Coffee was lovingly placed outside our door, including fresh lattes on our final day. I would definitely recommend this place to others and would love to stay here again!

Sanctuary Garden Bed & Breakfast
Caitlin and her husband, Peter, are caring, considerate hosts. They made me feel welcome in their beautifully appointed, light-filled home. They were open and friendly, interested in finding out who I was, while being respectful of my privacy. When I explained I didn't like to eat first thing in the morning, they went out of their way to prepare a yummy, healthy "to-go" breakfast I could take with me to the program I was attending. Caitlin even loaned me her favorite travel coffee mug for my tea. I was able to spend my final morning having breakfast with them and they prepared a delightful meal, replete with fresh fruits and flowers from their garden. We sat outside amongst the beautiful plantings and each shared with me a precious piece of their own life story as well as how they met. That's how I discovered what wonderful people they are. I would return there in a heartbeat. Staying at the Sanctuary provided a welcome contrast from the intensity of the program I was attending.

The Purple Chef's House
Beautiful house and amazing hostess! We both had a great time. Sharon is super friendly and very helpful. Can't wait to come again ❤️

Cozy space in relaxing semi-rural area.
Paul was an amazing host! Very helpful in regard to getting to know the surrounding area- also very accommodating during my stay! I will definitely stay here again next time I am up at Stratton. P.S., Paul makes really good waffles, lol.
Apartment rentals with breakfast

Cozy, Private & Great location for exploring VT !
Very lovely place located in a nice part of town. Mary and Lance were very welcoming and nice. We had a great stay and I strongly recommend this place for staying in Brattleboro.

~Serene Barn Retreat~
Very quiet. Brianna's beautiful light sculptures add so much to the visual beauty of the place. Echoing other reviews: the mattresses and pillows are super terrific. One challenge for us as an older couple -- the bathroom is on the first floor and the beds are upstairs. There are many well placed nightlights but it's still something to get used to if you have to get up in the night. A hummingbird came to visit!

Apartment on Main Street
We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

River View apartment
was communicative and friendly! Cute place and comfortable bed :)

Peaceful Forest Studio
We had a lovely stay. Our expectations from the listing description matched our experience pretty well. Liz and family were super friendly and good hosts. Our dogs had fun playing together. We wish we'd checked on the sauna earlier because it was a quick fix to get it up and running but we didn't realize we'd need help from the hosts until it was too late. Kitchen is functional but nothing fancy so we're glad we cooked a simple meal.
Bed and breakfast rentals with breakfast

Farm at Williams River House - Gloucester Suite
I absolutely loved our stay here - so much so that I’m currently looking at a calendar to see when we can come back! The beauty of the landscape, nice rooms/house and hospitality felt like a true treat!

Farm at Williams River House - Hawthorne Suite-ADA
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!

Queen bed + private bath, breakfast included
This is an idyllic setting for a beautiful home with super friendly and caring hosts. The large house, a retreat center with facilities for large groups, sits on a lake overlooked by a gorgeous modern treehouse. Tom and Ravi are excellent hosts and I enjoyed chatting and eating with them and learning about their vision for the property, communal and artistic, with nourishing food fresh from local farms, and a mix of interesting guests. This is the kind of place where you can truly unwind in natural green, wander the extensive grounds and connect socially if that suits you. The beds are comfortable, each room with its own bathroom, and the living rooms are spacious and with walls of books and artwork. Cannot recommend this place more highly. If you’re lucky enough to find availability, don’t hesitate!

Deluxe King, kitchenette,fireplace- Cider House 1
My boyfriend and I spent two wonderful nights in Cider House 1. We had a fabulous time. Peaceful and relaxing with beautiful fireplace.

Eva Blake House-Margaret's Room
We loved our stay at Eileen's! Eileen and her husband and wonderful warm people. The home is beautiful, decorations lovely, and the aesthetic was great! The home has a lot of history which added to the stay! Eileen even cooked us a delicious breakfast, served on beautiful china. She gave us recommendations for things to do around Bellow Falls and hikes around the area which we really appreciated! Would definitely recommend staying here and we're planning to visit again ourselves!

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

Bromley View Inn Suite #15
Nice stay at Bromley View Inn! The views were stunning, and the cozy, pet-friendly vibe made us feel right at home. The room was comfy, and we enjoyed relaxing in the lounge. Breakfast was a treat every morning. Enjoyed Fiddlehead IPA at Haig’s Sports Bar and at the 19th hole at Stratton’s Golf Course. Highly recommend this spot for a great location and welcoming stay!

Beautiful B&B room by a river and covered bridge.
If you want peace and quiet then this was the place. Lee and Bob were wonderful just and breakfast was delicious. We enjoyed a morning walk and getting to know our wonderful host.
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Dorset Field Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Brattleboro Ski Hill
- Hooper Golf Course
- Bretwood Golf Course
- Fox Run Golf Club