Guesthouse vacation rentals in Windham County

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Popular amenities for Windham County guesthouse rentals

Family-friendly guest house rentals

Guest favorite
A spacious bedroom features a king-sized bed adorned with colorful pillows, framed by large windows that offer views of the surrounding greenery. A decorative bench at the foot of the bed displays neatly arranged towels, complemented by bedside lamps on either side.
Guesthouse in Jamaica
4.95 out of 5 average rating, 156 reviews

The 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
The exterior of the guest house is shown, featuring a light green facade with a contrasting red garage door. A covered porch is visible, along with a decorative entryway. The surrounding area includes a grassy lawn and a clear blue sky, framed by trees in the background.
Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviews

The 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
A front porch features a wooden swing, two large windows, and a deep red door. The porch has white columns and a light blue ceiling, while a large flower pot sits on one side, adding a touch of greenery to the entryway.
Guesthouse in Putney
4.95 out of 5 average rating, 344 reviews

A 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..
A vibrant sunset is captured, displaying a mix of orange, yellow, and purple hues across the sky. The horizon is framed by distant hills and trees, while a soft mist blankets the lower landscape, suggesting a peaceful evening atmosphere.
Guesthouse in Chesterfield
5 out of 5 average rating, 24 reviews

1790 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

A double twin room features two wooden beds with intricate posts, positioned parallel to each other. Soft white bedding covers the beds, while a patterned area rug enhances the space. Complementary wall sconces provide illumination, and a door leads to the adjoining bathroom.
Private room in Newfane
4.82 out of 5 average rating, 11 reviews

Yogi & 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
A two-story house with a covered porch featuring wooden posts and a white railing, surrounded by colorful autumn leaves. A large yard is visible, and the entrance is accessible from the porch. The structure evokes a welcoming atmosphere in the serene landscape.
Guesthouse in Chester
5 out of 5 average rating, 17 reviews

New 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!
A cozy queen room features a wooden bed with a plaid blanket. Two artworks hang on the teal wall, complemented by matching wooden nightstands. Soft lighting is provided by a lamp on one side, while natural light enters through an unseen window.
Private room in Newfane
5 out of 5 average rating, 3 reviews

Queen 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
The exterior of the home features large, multi-paned windows that allow ample natural light. A sloped roof is topped with a weather vane, while a snow-covered yard leads to the entrance. The overall structure exhibits a charming architectural design.
Guesthouse in Dover

Upstairs Rice Hill Retreat

Guest house rentals with a washer and dryer

A spacious barn-house is surrounded by a snowy landscape, illuminated by soft outdoor lighting. The exterior features a sloped roof and a cupola, with large windows allowing for natural light. The driveway is clear of snow, providing easy access.
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.
A spacious studio features a wooden bed with a colorful striped blanket, an area rug, and a desk with a lamp. A cozy seating arrangement surrounds a coffee table, while natural light enters through large windows leading to the outdoor deck. A ceiling fan provides a comfortable atmosphere.
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.
A spacious garage-converted studio includes a comfortable sofa and a striped armchair. Large windows provide natural light, while a wooden coffee table sits at the center. A bar-height table with stools is positioned near the garage door, enhancing the open feel of the room.
Guesthouse in Weston
4.15 out of 5 average rating, 13 reviews

1BR 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.
A well-appointed sleeping area features a large bed covered with a quilt showcasing a patchwork design, complemented by two matching pillows. A wooden rocking chair is positioned beside the bed, with a small lamp providing soft illumination in the cozy space.
Guesthouse in Stratton
4.78 out of 5 average rating, 37 reviews

Stratton 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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