
Guesthouse vacation rentals in Windham County
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Top-rated guesthouses in Windham County
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
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Popular amenities for Windham County guesthouses
Family-friendly guesthouses
Top guest favourite

Guesthouse in Jamaica
4.95 out of 5 average rating, 155 reviewsThe Chick Inn
LaurenRating, 5 stars5 months ago
great stay! peaceful location! fun games and painting supplies available. the bed was not too comfy as it is very hard and springy, but made do for one night!
Superhost

Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
MargaretRating, 5 stars22 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 favourite

Guesthouse in Brattleboro
4.98 out of 5 average rating, 228 reviewsLight Filled Loft in the Vermont Countryside
RebeccaRating, 5 stars1 month ago
Loved the place - so beautiful. Everything was as pictured. Loved the heated toilet seat! Just need to know it is a dirt road for a bit before 797, and if there in rainy season there are deep ruts. And steep stone steps to the loft and then a railed stairway. So if anyone has any mobility issues they need to know ahead of time. Shawn was gracious and brought over some coffee beans for the morning brew. Close to downtown Brattleboro. Missed going for a walk. Such a lovely property.
Guest favourite

Guesthouse in Putney
4.95 out of 5 average rating, 343 reviewsA Vermont Carriage House
JackieRating, 5 stars1 month ago
Very nice and cozy place to stay. We stayed during a rainy, chilly weekend and were able to use the fireplace each day. Alex provided us with enough care, instructions and wood to enjoy the fireplace for our entire stay. The local recommendations were a plus. Alex is super friendly and responsive.

Guesthouse in Chesterfield
5 out of 5 average rating, 24 reviews1790 Historic Home in Chesterfield for Five Guests
MaryRating, 5 stars9 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!!
Guesthouses with a patio

Private room in Newfane
4.82 out of 5 average rating, 11 reviewsYogi & artist retreat center
JoshRating, 5 stars19 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.
Top guest favourite

Guesthouse in Chesterfield
4.99 out of 5 average rating, 79 reviewsHouse on a hill
CynthiaRating, 5 stars3 weeks ago
Very close to Keene and Vermont. Great area overall. The house was a great size for two people and a dog. Very clean and welcoming. Thank you for a great stay!
Guest favourite

Guesthouse in Chester
5 out of 5 average rating, 17 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
VeronicaRating, 5 stars2 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 stars20 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!
Guesthouse rentals with a washer and dryer

Guesthouse in Weston
4.15 out of 5 average rating, 13 reviews1BR dog-friendly mtn cabin with fireplaces
IanRating, 5 stars14 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 stars2 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
- 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 Sugarloaf State Reservation
- Mount Greylock Ski Club
- Pineridge Cross Country Ski Area
- Ekwanok Country Club
- Hooper Golf Course
- The Shattuck Golf Club
- Baker Hill Golf Club
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Stump Sprouts Ski Touring Center
- Northern Cross Vineyard
- Clarksburg State Park
- Peebles Island State Park
- Hancock Shaker Village