
Holiday rentals with breakfast in Windham County
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Top-rated Holiday Accommodation with Breakfast in Windham County
Guests agree: These breakfast rentals are highly rated for location, cleanliness and more.
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Holiday 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
Jessica was a wonderful host. In some ways a Classic air bnb which I appreciated; Simple and warm and inviting home. I slept very well and could walk easily to town. Next time I will Go to her restaurant !

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

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.

Peaceful Room in Brattleboro
Apartment rentals with breakfast

Cozy, Private & Great location for exploring VT !
I really enjoyed the space. It was clean, free of clutter and very cozy. The bed was comfortable and included a desk for workspace. It was quiet and had all the amenities you would need. I loved the gas fireplace and outdoor patio. I plan to return to the apartment in the future and highly recommend this location. Mary (the host) was very friendly and helpful. I had a great stay!

~Serene Barn Retreat~
Charming and very comfortable living space. As listed and in pictures. Brianna was wonderful with instructions and recommendations in the area. Much to do in the area, convenient access. Thank you, Brianna!!

Apartment on Main Street
Perfect stay for our short trip! Whitney is wonderful and so responsive!

River View apartment
Susan’s place was quiet, clean and lovely. Close to town, but still in a wooded area. The apartment is well designed with everything you could need, including delicious coffee.

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 - Essex Suite
This was my first Airbnb experience. From the very beginning, John and Kathy were excellent hosts. They come across as just genuine and likeable people - it really feels like you’re staying with friends. Not to mention, they are SO kind in opening up their entire (gorgeous) home and property to you. They make it clear that while you’re there you have free range to explore the grounds or utilize the fun on-site things such as the fire pit and relaxing common areas. The breakfast served each morning was so thoughtful and delicious; my husband and I really felt like we were being spoiled!! Speaking of spoiled, idk how I’ll ever be able to have a better Airbnb experience than John and Kathy provided as they really set the bar high. Looking forward to booking our next visit here for sure.

Apple Hill Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
The Wilmington Inn is always a favorite place to stay! It's always quiet and so convenient to restaurants and the shops--we'll be back!

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
This is a very comfortable and pleasant B&B in a well-preserved and beautiful old house--they had a little guide to the history in each room. The beds are very comfortable to sleep in and the temperature in the rooms is nice and warm. Breakfast was delicious. The best thing about it was the hosts: they are very friendly and attentive. You get the impression they really like their guests and enjoy sharing their beautiful home. This place is an absolute gem.

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
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Saratoga Race Course
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Ekwanok Country Club
- Bretwood Golf Course
- Hooper Golf Course
- Baker Hill Golf Club
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Northern Cross Vineyard
- Pineridge Cross Country Ski Area
- Willard Mountain
- Hancock Shaker Village
- Dorset Field Club
- Things to do Windham County
- Things to do Vermont
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- Nature and outdoors Vermont
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