
Guesthouse vacation rentals in Windham County
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Top-rated guesthouse rentals in Windham County
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Guesthouse in Jamaica
4.95 out of 5 average rating, 156 reviewsThe Chick Inn
GordonRating, 5 stars1 week ago
stayed three nights, very unique and lovely place! Beautiful Vermont surroundings, friendly animals, plus lots of chicken action! Very cozy space. Friendly and communicative hosts, Erica showed us around and told us all about the chickens.
Superhost

Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
MargaretRating, 5 stars23 months ago
We were in town for a family wedding and this was the perfect place for 20 or so of us to spend the weekend. Everything was great. We were so comfortable and had so much fun! Thank you to Meiling, Martin, Mayra, and all the folks who assist them with housekeeping and logistics. Hope to find an excuse to return, as everyone was sorry when our stay came to an end. Highly recommend without hesitation.
Guest favorite

Guesthouse in Putney
4.95 out of 5 average rating, 344 reviewsA Vermont Carriage House
Ann-MarieRating, 5 stars5 days ago
Alex’s place was as described. It was clean and had a well equipped kitchen and great back yard with Adirondack chairs looking off to the distance. We were racing around and could not enjoy much. The place is ideal for a couple or two friends (one when bed?). The stairs to the bedroom are very steep as described so this would not be the best spot for all. It is closer to Putney than you might think so do not let that be a concern..

Guesthouse in Chesterfield
5 out of 5 average rating, 24 reviews1790 Historic Home in Chesterfield for Five Guests
MaryRating, 5 stars10 months ago
We enjoyed our stay at Catherine’s, it was very comfortable and easy to feel at home. The back porch was our favorite spot, the sunset view of meadows, fields, valleys, and mountains is unparalleled! There were many bunnies, birds, and chipmunks to watch. We were there around the Fourth of July and even saw some fireworks over the mountains. The beds are comfortable, the kitchen is stocked with plenty of dishes and cooking utensils. Anything we needed beyond what was there was able to be kindly dropped off right away. It was so helpful to have a half bath on the first floor. We didn’t use the living room much because the porch was the place to be, but it was lovely with a beautiful fireplace. We will definitely be back again!!
Guest house rentals with a patio

Private room in Newfane
4.82 out of 5 average rating, 11 reviewsYogi & artist retreat center
JoshRating, 5 stars20 months ago
Thomas has a beautiful yoga retreat type of resort up in the mountains of Vermont. The place is stunning. The rooms are very comfortable and they give you a delicious breakfast. It's definitely worth the time and money to stay with Thomas. 5 star rating. I hope to come again with my family.
Guest favorite

Guesthouse in Chester
5 out of 5 average rating, 17 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
VeronicaRating, 5 stars3 months ago
Jeff’s place was perfect for our two family ski trip. Our kids especially enjoyed the basement and there was plenty of room to spread out. Well equipped kitchen and big open dining/kitchen/living area were great for cooking and eating together. We had a great stay!

Private room in Newfane
5 out of 5 average rating, 3 reviewsQueen bed + private bath, breakfast included
SebastianRating, 5 stars21 months ago
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!
Superhost

Guesthouse in Dover
Upstairs Rice Hill Retreat
Guest house rentals with a washer and dryer

Guesthouse in Stratton
Adorable 2 bedroom guest house located on Stratton
LisaRating, 5 stars44 months ago
This is an absolutely pristine venue. Up in the mountains and surrounded by fall foliage that will amaze!! Gives the feeling of blessed, lovely isolation. Super clean, well appointed, super easy entry with keypad entrance instead of the hassle of a key. Communication by the host was superb and timely—like immediate. The barn is next to a phenomenal home— can I say family reunion extraordinaire!! Though we were here in the fall, my friend and I agreed it would be fabulous to come over the winter holidays to ski or just feel beautifully wintry for the holidays. Highly recommend!!!! Thanks Riley.

Guesthouse in Newfane
Private Retreat, Fast Wifi Near Skiing Brattleboro
AnnaRating, 5 stars53 months ago
An incredible place to wake up and be greeted by the wonder of winter mountain sunrises! Pastels across the farmscape in the afternoon are equally mesmerizing. The loft itself is filled with light; its many windows and angled ceilings maximize the views. Dave and Scott have done a fantastic job creating and appointing a studio floor plan with designated sleeping, living, cooking, dining, bathing and storage areas. The dishwasher is so quiet you can sleep with it on! Coffee and tea are thoughtfully available, as are other extras like laundry detergent. Cookware and kitchen gadgets are diverse and more than adequate. The closet is well stocked with cleaning supplies. The gas fire stove makes the space feel cozy and amply warms against the cold outside. Having washer and dryer appliances on site makes such a difference for a long term stay. Not all places in the area I have rented offer laundry, so take note of this extra bonus. On top of all the loft accolades, it is the owners who make staying on property most favorable. Scott and Dave were always prompt to respond to any inquiries and one step ahead of me when it came to what to do when it snowed. They have put a lot of effort into COVID precautions as well as into providing a space that is welcoming, aesthetically pleasing and optimally functioning.

Guesthouse in Weston
4.15 out of 5 average rating, 13 reviews1BR dog-friendly mtn cabin with fireplaces
IanRating, 5 stars15 months ago
Options are limited when we travel our with two dogs so we felt very fortunate to find the home in Weston. It was perfect for the two of us and our two dogs. The home had most of what you would expect as far as extras and everyday items. We loved the area we were in and the proximity to Londonberry and southern resort mountains. I would recommend the home to anyone with a small group. We will rebook next year if the cost doesn't increase.

Guesthouse in Stratton
4.78 out of 5 average rating, 37 reviewsStratton Quaint Guest house
XinciRating, 5 stars3 months ago
Anna is an amazing host - super friendly, thoughtful, and incredibly helpful! She went above and beyond to assist us when our car ran into some issues and offered us so much valuable recommendations and support, making our stay much smoother. Her kindness and willingness to help truly made a difference in our trip. The place itself was cozy, well-maintained, and conveniently located close to the Stratton ski resort. We had a wonderful experience and would absolutely recommend staying here!
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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
- Hildene, The Lincoln Family Home
- Clarksburg State Park
- Ekwanok Country Club
- Hooper Golf Course
- Bretwood Golf Course
- Brattleboro Ski Hill
- Fox Run Golf Club
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