Cottage vacation rentals in Windsor County

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Popular amenities for Windsor County cottage rentals

Cottage rentals with a hot tub

Guest favorite
A beautiful white clapboard house is framed by lush greenery and colorful flowers. The stone steps lead to the main entrance, while large windows offer glimpses of the interior. The landscape features well-maintained grass and foliage, set against a clear blue sky.
Cottage in Woodstock
5 out of 5 average rating, 29 reviews

2 person SunCottage - Hot Tub Solar Geothermal

DanaejahRating, 5 stars10 months ago
The house was beautiful and had a bunch of nature space and can tell is very kept up and taken care of. The house inside is beautiful and clean. The hot tub with the nature view is amazing. Deff would give this place a 10/10 and recommend to people looking for a private and peaceful area. Only thing is no service if not from area and restaurants and grocery stores are alittle far out but other than that great place to stay!
Guest favorite
A modern kitchen is equipped with wooden cabinetry, stainless steel appliances, and a dark countertop. Natural light fills the space through a window, illuminating the cooking area. A bar stool is positioned at the kitchen island, enhancing the functional design.
Cottage in Ludlow
5 out of 5 average rating, 7 reviews

NEW Guest Cottage on 23 Acres

AndrewRating, 5 stars8 months ago
We had such a great weekend at the Revival. Mark and Dana did an amazing job with this place. The house is gorgeous and so clean. The view is spectacular, and they provide you with so many activities to enjoy on the property. Close enough to be able to walk into Ludlow. This place really has everything you could possibly ask for. We are very much so looking forward to going back.
Superhost
Aerial view captures the vibrant fall foliage surrounding the mountain home, with a mix of green, orange, and yellow trees. The distant mountains, partially covered in green, are visible under a gradually darkening sky, creating a serene natural backdrop.
Cottage in Killington
4.83 out of 5 average rating, 69 reviews

Vt Summer Getaway: Hot Tub, Golf Hiking & More!

TimothyRating, 5 stars2 months ago
Great house with plenty of space and beds. Living room had ample couches and great for our group to hang out there with the fireplace and hot tub off the back deck of kitchen. Kitchen had all necessary cooking pots/pans/utensils. Easy communication with the hosts and would return.
A serene lakeside view showcases a wooden dock with two chairs positioned toward the water. Soft reflections of trees and clouds are visible on the calm lake's surface, while lush greenery surrounds the area, providing a peaceful natural setting.
Cottage in Ludlow
4.79 out of 5 average rating, 34 reviews

3BR lakefront with dock, swim platform, & firepit

LaurenRating, 5 stars1 month ago
This was our second time here, and we loved it just as much as we did the first time. Our dog really enjoys it as well!
Top guest favorite
The cottage, constructed from natural logs, is framed by lush greenery. A steeply pitched roof with a metal covering adds character. The inviting outdoor space features a patio area with seating, accompanied by a stone fire pit and cozy landscaping.
Cottage in Barnard
4.95 out of 5 average rating, 38 reviews

Andas Hus: Little Luxury

JessRating, 5 stars2 weeks ago
Staying at Andas Hus was an Airbnb experience on another level. This little cottage has everything that you could ever need for an extended getaway- we did so much cooking, wandering, made full use of all of the tech, and enjoyed the hot tub for several nights. We had four adults sharing the cabin and it was more than enough room for us. Matt was super responsive and kind when we had questions about the stay. I'll absolutely be recommending Andas Hus to any of my friends and relatives looking for a New England getaway, and maybe we'll be back someday!

Pet-friendly cottage rentals

Top guest favorite
A cozy sleeping area is presented with a spacious bed dressed in a light quilt featuring subtle sailboat patterns. Decorative pillows add a pop of color. Nightstands are placed on either side, each holding a lamp and framed artwork is displayed above the bed.
Private room in Strafford
5 out of 5 average rating, 7 reviews

“Celia” room with meditation nook

AnneRating, 5 stars19 months ago
Always a pleasure to stay at Hope’s place. Feels like home away from home.
Superhost
A spacious living room is furnished with a large sectional sofa and a comfortable armchair. A coffee table sits in the center, while large windows allow natural light to fill the room. Greenery from a potted plant adds a touch of warmth and comfort.
Cottage in Mendon
5 out of 5 average rating, 6 reviews

The Mendon Cottage: Cozy Home. Killington / Pico

BrianRating, 5 stars3 months ago
Place is exactly as advertised. One of our party was a non-skier (aka designated driver), which made the location even better. A couple of minuted to Pico, 10 minutes to Killington and 10 minutes the other direction to Rutland with all the conveniences of town.
A cozy sleeping area is showcased, featuring a wooden bed covered with a white blanket and a patterned rug beneath. A chest of drawers stands nearby, and a window with a light-colored shade allows natural light to filter in. An electric fan is positioned below the window.
Private room in Strafford
5 out of 5 average rating, 6 reviews

“Matisse” bedroom in a country cottage

AshtonRating, 5 stars8 months ago
Hope’s Vermont cottage was fantastic. We were greeted by Zephyr (friendly cat) and Hope upon arrival. Her place was easy to find and Google maps took us right to the cottage. I did forget to look up the check-in instructions before getting there and found out I had no cell service with Verizon upon arrival. Even with no instructions, Hope’s cottage was easy to navigate to the front door and Hope was extremely welcoming. The cottage was immaculately clean and the vibe was homey and warm. Woke up to beautiful mountain views. Definitely would stay again in Hope’s idyllic country cottage!
The exterior of a cozy mountain cottage is framed by two trees, showcasing a welcoming entryway. A porch is visible, complemented by stacked firewood and a seasonal wreath. The surrounding landscape features a lawn and rocky outcropping, offering a sense of natural tranquility.
Cottage in Mount Holly
4.98 out of 5 average rating, 58 reviews

Cozy COTTAGE- ski, swim, hike, foliage, near Okemo

KarenRating, 5 stars10 months ago
The surroundings were beautiful and we loved watching the sun set over the mountains. The cottage was very clean and we really appreciated how well set up the kitchen was. Ron was friendly and responsive. We enjoyed finding swimming spots, local hikes and maple ice cream. We highly recommend the cottage and hope to return someday!
Guest favorite
A welcoming outdoor space features a small round table with wrought iron chairs, surrounded by blooming flowers in planters. The entrance to the cottage is adorned with a 'WELCOME' sign, and natural light illuminates the area underneath the shaded porch.
Cottage in Londonderry
4.87 out of 5 average rating, 71 reviews

Vermont Country Cottage(Near Village w/Magic View)

DonnaRating, 5 stars5 days ago
The little white cottage was lovely with everything we needed for a comfortable relaxing weekend. Like every other weekend this spring...it rained...but the cottage was still bright and cheery. So much to do , see, and eat so close by. We'll be back!
A cozy cottage is nestled among snow-covered trees, showcasing a tranquil winter landscape. The exterior features large windows and white walls, while a wooden deck is visible at the entrance. Snow blankets the ground, creating a serene and inviting atmosphere.
Cottage in Londonderry
4.86 out of 5 average rating, 29 reviews

VT Winter Getaway

GeorgeRating, 5 stars64 months ago
Stayed at Nicole’s cottage for a long ski weekend with my wife and pup. Exactly what we were looking for in regards to a private, clean, secluded getaway for a few days. She had the heat turned up (gas fireplace) which was welcoming for our arrival in the cold. Nicole was great in touching base before and during the stay making sure everything was in order. She also shared tips on local shops/eateries making it easy to prearrange. Good proximity to slopes. Will look to stay again in the future.
A cozy cottage exterior is showcased with large windows and a sloped roof, surrounded by lush greenery. A spacious porch features comfortable seating adorned with colorful potted flowers. Striped awnings provide shade over the outdoor space, inviting relaxation during warm days.
Cottage in Newport
5 out of 5 average rating, 3 reviews

Lakeside Cozy Cottage. Peaceful and Serene.

BradleyRating, 5 stars56 months ago
Wonderful escape from city life. This place is the epitome of serenity and relaxation. Ellyn is a wonderful, communicative host. Lots of hikes, lake activities and breweries made this a great stay for us. Go unplug here. Can’t beat the morning view on the lake.
The exterior of the farmhouse is shown, featuring a light-colored façade with multiple windows. A sloped roof and a small porch area are visible. Surrounding greenery includes trees and tall grass, contributing to a peaceful country setting.
Cottage in Ludlow
4.9 out of 5 average rating, 101 reviews

Antique Ludlow Farmhouse - 12 minutes to Okemo

SpencerRating, 5 stars5 months ago
The host is very responsive and ensures that you are all set with the Wi-Fi and move in process. Directions to the property are clear and concise. The house is beautiful and spacious.

Private cottage rentals

Top guest favorite
A screened-in porch features a glass-top table surrounded by four yellow chairs, providing a comfortable space for dining or relaxing. The porch overlooks a green yard with nearby colorful structures, enhancing the connection to nature.
Cottage in Peru
4.96 out of 5 average rating, 78 reviews

Moon Beam Cottage--A cozy and welcoming retreat

KristenRating, 5 stars1 month ago
We so enjoy staying at Melissa’s place. It has everything you could need and is an amazing location. We discovered the catamount xc trail is only a short distance away.
A wooden deck is surrounded by lush greenery and vibrant orange flowers, enhancing the outdoor space. Nearby, a shed with a metal roof is visible, adding character to the setting. The area is peaceful, with well-maintained plants providing a natural backdrop.
Cottage in Randolph
4.89 out of 5 average rating, 44 reviews

Comfortable White Cottage

JulieRating, 5 stars11 months ago
Mary’s place was very quaint. Easy to get into. She left wonderful directions. Very clean. She had a lot of little extras that made you feel like home. She has true passion for flowers that was evident around the outside of her home. Absolutely beautiful It was fantastic to watch the birds interact with the flowers.
Guest favorite
A serene view of Lake Rescue at sunset, with sunlight reflecting on the water's surface. A private dock extends from a grassy beach area, surrounded by trees and gentle slopes. Kayaks and a tent are placed nearby, enhancing the peaceful lakeside atmosphere.
Cottage in Ludlow
4.93 out of 5 average rating, 44 reviews

Ludlow Lakefront Home

JoshuaRating, 5 stars4 months ago
We felt right at home in this lovely rustic cabin on the lake. We had to work with Thomas to solve some unfortunate complications during our stay, including a dead rodent in the sink, a lack of sheets and towels, and taking our trash with us. However, we loved the home and had a wonderful weekend in the area. Thank you!
Top guest favorite
The bathroom features a compact white sink with a polished chrome faucet and towel ring. A decorative red-framed mirror hangs above the sink, reflecting the warm tones of the walls. Soft white towels are neatly positioned on the towel ring, adding to the space's functionality.
Cottage in Killington
4.96 out of 5 average rating, 24 reviews

Bright & Homey 3 bedroom near Killington & Pico

BobbyRating, 5 stars2 months ago
We enjoyed our stay at Madelyn’s place for our weekend ski trip. It was conveniently located close to Killington and was fairly spacious.
A bright bathroom is presented with white shiplap walls and a window that allows natural light to illuminate the space. A modern sink and mirror are featured, complemented by neatly arranged towels. Framed artwork adorns the adjacent wall, adding a touch of character.
Cottage in Thetford
4.89 out of 5 average rating, 93 reviews

Riverside Cottage, Campanoosuc North

UlrikeRating, 5 stars5 months ago
We really enjoyed the cottage next to the river. It was during Xmas break so quiet and snowy. You can hear the water current of the river out back, so it had a peaceful feeling. The interiors were just renovated so felt like a brand new home. The detailing was very well done and felt more like a home than an Airbnb. We definitely recommend it for a family as there are two bedrooms and a loft with 2 beds. David was very responsive so no worries. Also the area has nice Vermont towns to visit. Hanover, NH is nearby - home of Dartmouth College.
A peaceful porch area features a hammock suspended in the shade, with views of the lake visible beyond. A small table and chair are positioned beside the hammock, creating an inviting space for relaxation or quiet reflection.
Cottage in Fairlee
4.83 out of 5 average rating, 18 reviews

Lake Fairlee Porch Views from The Edgevale Gem

DavidRating, 5 stars3 weeks ago
Olivia is a wonderful hostess. We have rented properties from her in the past and have always been happy with our stays.
Guest favorite
A spacious dining area is highlighted by a long wooden table surrounded by benches and chairs. Large South-facing windows frame scenic views of the greenery outside, while overhead, a unique light fixture adds visual interest. The wooden floors contribute warmth to the open space.
Cottage in Vershire
4.92 out of 5 average rating, 92 reviews

The Vershire Fortress

MarcelaRating, 5 stars2 months ago
What a delight! I was here to get away and write for a few days, and it was exactly what I needed. beautiful views, comfortable, cheerful, and elegant. It has everything you could need, and it was all easy to figure out. The only issue I had was the drive to and from the house bc it is peak mud season and the roads were in rough shape. I was really glad I had the recommended all wheel drive car bc you slide around quite a bit otherwise.
Guest favorite
A stone pathway is lined with soft glow from solar lights, guiding the way through a lush green yard. Flower pots with vibrant yellow and pink blooms add color to the scene, creating an inviting atmosphere for outdoor enjoyment.
Cottage in Weston
5 out of 5 average rating, 39 reviews

Ski cottage near Okemo, Bromley, Stratton

TaraRating, 5 stars3 months ago
The place was just as described - cute as a button. The location was close to the ski mountains and had plenty of room to spread out! The kitchen was well appointed and the kids loved the triple bunk room. We will definitely be back.

Destinations to explore