
Holiday rentals with breakfast in Windsor County
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Top-rated Holiday Accommodation with Breakfast in Windsor County
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Holiday House Rentals with breakfast

Private fireplace suite & luxury bath - Killington
Josiane and Todd were great. Like staying with friends. They’re interested in you and share but only if you want. Breakfast was delicious and she accommodated my gluten allergy. A new experience to interact with the host in this way yet still private suite. Great time!

Studio Apartment in Beautiful South Woodstock
We had a great stay here! Perfectly clean with everything you’d need for a good stay. We would definitely come back and stay again very cozy place in a great location.

River Setting Close to Dartmouth
You couldn't ask for a better host than Lisa, the owner of this property ( and her husband Ken! ). She made us feel immediately welcomed, was flexible in terms of our arrival, catered to our needs, and provided a wonderful place to stay to enjoy the nearly non-existent fall foliage during the weekend we chose. It was not a wasted trip, however, because everything about our long weekend was great. The nearby town was close enough to go for meals and had an awesome menu, Dartmouth and the town of Hanover were close by and lovely to visit, and just enjoying the ambience of Lisa and Ken's house was a treat. She provided a very tasty continental breakfast of locally made jam, bread, yogurt, granola, plenty of fruit, and good coffee. This was a nice feature of this airbnb listing because we could leisurely get up, eat something and not have to rush out to the town to have breakfast each day. The smell of coffee in the guest room was heavenly to wake up to! Lisa and Ken were interesting and easy to talk to and we loved every minute of our stay here and would recommend it to anyone.

Secluded Home, Breathtaking Views, Dog Friendly.
This was such a welcome escape from city life! Property so peaceful and beautiful. View from the back yard is gorgeous - I love the fall colors, hilltops, sky and clouds! House was perfect in always for my husband, our Labrador and myself - cozy and warm. Everything we needed was in the kitchen. Jon was very good with communication and suggests for outings at near by areas. Loved cruising the streets of Woodstock and Quechee. Fabulous walk at the Quechee Gorge. Loved the Woodstock Farmers Market - dangerously delicious treats of all kinds! Everything was easy to get to. People were kind when we were out in the community. It will be on our list to revisit! Thank you Jon for offering your home.

Mountain and Valley Views 1C
Ok, the driveway was somewhat intimidating, but Andrew had prepared us for it. And it was worth it! The house and views were great! Andrew was an excellent host, the room and bathroom were as expected.

Vermont private retreat with gorgeous views.
I truly felt like I was staying at my grandmothers house, and I mean that in the very best way. The house was cozy, very well taken care of and so nicely decorated. I loved all of the quilts throughout the house. The view was probably my favorite thing about the location. You could see the farm below, and sometimes the cows would be outside, which were nice to see. We made a lot of day trips while in Vermont. I recommend visiting Shelbourne Farms which sits on 1400 acres. Also, Sugarbush Farm for maple syrup and cheese tastings. If you need meat for your dinner ideas, I highly recommend Roma's Butchery.

Cozy private room - Killington
The room was clean, quiet, dark, and relaxing. The location felt safe and was quiet, very close to skiing at Killington and Pico mountains. There was a steam room in the bathroom which guests could use which was really fantastic! Josaine and Todd were wonderful hosts. They were very welcoming, cooked delicious breakfasts, and made me feel like I was a friend visiting. Would highly recommend!
Apartment rentals with breakfast

Studio - For One - at Dartmouth College
Without a car, Sandy’s Airbnb is an easy & beautiful walk from Hanover Inn. There happens to be a free shuttle in Hanover to get to all points around the college and to DHMC (which is across town line, in Lebanon, 3 miles away) which allowed me to visit a sick friend with support, comfort and ease.

Premium Suite (Mountain Sports Inn)
Great place in a great location. Awsome value, would stay again for sure.

Canyons Unit: 1 mile to F&W Summer Camp w/ HOT TUB
Amazing location! Sabrina’s place was super cozy and very clean! We would definitely stay again.

Moguls Unit:1 mile to F&W Camp w/ HOT TUB
We loved it here! It was a short drive to Killington Resort, and there were plenty of great restaurants nearby. We especially enjoyed the beautiful walking trails throughout the property and the cleanliness of the space. This was an extremely affordable and pleasant ski weekend!
Bed and breakfast rentals with breakfast

The Fan House, A Vermont Country Home
We stayed 2 days and loved Sara’s place for its privacy and cozy one bedroom with individual bathroom and shower and bath tube. Sara and Jake are communicative and friendly. Very wonderful place to spend the weekend.

King Room with Private Bath - The Trailside Inn
Cozy rustic room with comfortable bed after a day of skiing! We initially were disappointed by the bare bones furnishing and the large gaps between their wood floorboards. However, the delicious breakfast, helpful hosts, and beautiful location won us over.

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.

Balm of Gilead B & B Blue Suite
nothing but praises for Sarah’s place! Her radiance and hospitality is just so heart warming! This is our group’s second year of staying at Sarah’s and we love it! Looking forward to be back! Love the breakfast Sarah serves - best way to start a ski day. Definitely need to give her jomemade Hollandaise sauce a try!

Historic Hubble Shire Farm Inn--French Queen
We have found the best way to experience New England is to get out of the heavily touristed areas on back rounds and small towns. This is out of the way, but it is a beautiful drive an area. This is a classic bed-and-breakfast experience in a historic with a warm and welcoming guest, not a newer, colder AirBNB experience. We ordered dinner ahead of time with Amanda which I highly recommend because she is an excellent cook. We enjoyed everything about our stay here and will return next year.

Stay at the largest Colonial Revival Mansion in US
Absolutely perfect and amazingly accommodating. The mansion was actually closed on Thursday as they were preparing for a large event for the weekend but still found a beautiful, private place for me to stay for the couple nights I needed. Diane met me at the door, showed me around the property, and gave me recommendations for local food. She offered her cell number and the promise to help with anything I needed. The grounds are beautiful and located next to a park with walking paths. The room was perfect for what I needed; shower, kitchenette, and really comfortable bed. I will stay again anytime I’m in the area. My since thanks to Diane, Andy, and the beautiful, old New England inn.

The Governor's Inn - Ann's Room
Staying in the Governor’s Inn was like taking a step into the past—in a good way. The Inn, itself, is pristine and well-kept, with period decor and furniture. Our room was spacious and cozy. The 3-course breakfast was amazing. Best of all, the hosts were warm, welcoming, and helpful. They truly made us feel at home.

Thorny Hills Farm
We loved our time at John and Sues. The area was absolutely stunning (but a little hard to find in the dark if you follow google maps instead of Sues directions) it was very cozy and picturesque and Queeny the goat was a favorite. We hope to go back someday and bring our kids with us.
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Hooper Golf Course
- Bretwood Golf Course
- Dartmouth Skiway
- Veterans Memorial Recreation Area Ski Hill
- Baker Hill Golf Club
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Santa's Land USA
- Brattleboro Ski Hill
- Things to do Windsor County
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