Vacation rentals in Windsor County

4.98 out of 5 average rating, 48 reviews

A hot tub is depicted with glowing blue lights illuminating the water and steam rising into the night air. The structure above is part of a covered porch, providing an inviting area for relaxation outside.

Home in Cavendish

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views

RickyRating, 5 stars1 month ago

Awesome place! All the games in the basement gave us something to do while hanging inside the house. It’s great being able to come back after a long day of snowboarding and relaxing in the hot tub. The kitchen had everything we needed to cook. Only thing “negative” I could say is we couldn’t find any trash bags for the trash cans but obviously not that big of a deal. Overall I would 100% recommend and would definitely stay here again, without a doubt

4.89 out of 5 average rating, 184 reviews

A spacious backyard is shown, featuring a well-maintained lawn surrounded by lush greenery. A deck is visible, along with a hot tub and a fire pit seated with outdoor chairs. Scenic mountain views can be seen in the distance under a blue sky.

Home in Rutland

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

MatthewRating, 5 stars2 days ago

This place was beautiful, and so much bigger than the pictures!! We loved how private it felt, and it was just a short walk to downtown! Would recommend to anyone coming to this area, and would gladly stay again ourselves!!

5 out of 5 average rating, 5 reviews

A serene outdoor space features two Adirondack chairs positioned around a fire pit, surrounded by lush green grass and a backdrop of dense trees. The calming natural setting invites relaxation and outdoor gatherings.

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

SeanRating, 5 stars2 months ago

The Mendon Cottage is clean, cozy and private. It’s just a 15 minute drive to Killington base, even in a fairly decent snow storm. There are trails behind the property that offered some good hiking for our doggo (they’re made for snowmobiles, but we didn’t spot one during our stay). The property delivers on its main promise: a less pricey alternative to staying at Killington, with very little inconvenience for the ski bums. Unless you simply can’t live without the ability to take the shuttle and ski off the mountain to your rental, you really can’t go wrong with this property. (It snowed our entire stay and the private road and driveway were plowed repeatedly and always navigable.)

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

ChristopherRating, 5 stars1 month ago

Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.

4.93 out of 5 average rating, 14 reviews

A screened-in porch features colorful seating, including blue and green chairs, surrounding a small table. Natural light filters through large windows, revealing views of the lake and surrounding greenery. String lights hang from the ceiling, adding a cozy touch.

Cabin in Plymouth

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo

MadelineRating, 5 stars5 months ago

I decided to take a spur of the moment long weekend and Alecia and John’s place looked like it would be the perfect spot to get away and relax. It was everything I thought it would be and more! The views of the lake are stunning and the house is so cozy. 10 out of 10 would recommend.

5 out of 5 average rating, 10 reviews

A modern cabin is situated among snow-covered trees, showcasing large windows that reflect the evening sky. The triangular roofline and dark exterior contrast with the white snow, while a cozy glow emanates from within.

Home in Peru

Highland Haus: stunning ski getaway with hot tub

ChristopherRating, 5 stars1 month ago

Beautiful home that is about 15min from Manchester, which is wonderful to walk around (shops, restaurants). The home is secluded on a nice piece of property in the woods. It was a charming getaway with a wood-burning fireplace and great amenities (games, dart board, hot tub, etc). Highly recommend!

4.97 out of 5 average rating, 30 reviews

An indoor jacuzzi room features ample natural light streaming through multiple windows. The room is surrounded by wooden paneling, enhancing the cozy ambiance. A spacious, circular jacuzzi is positioned in the center, complemented by a built-in bench along one wall.

Cabin in Killington

Luxury Ski Cabin, 2 bedrooms, den & 3 bathrooms

JakeRating, 5 stars1 month ago

Sadie’s ski house was fantastic! It had everything we needed for a group of five adults and a child, and was only a short walk to a ski trail (great eastern). Check in/out was very easy. I’d be happy to stay again!

4.8 out of 5 average rating, 10 reviews

A spacious family room features a large, light-colored couch and a cozy area rug. A stone fireplace serves as the focal point, surrounded by large windows that provide a view of the wooded surroundings. A coffee table and an armchair enhance the inviting atmosphere.

Home in Hartford

Pet-Friendly, Mountainside Home | Treetop Lodge

AnneRating, 5 stars4 months ago

We stayed here while visiting family in Hanover forThanksgiving. A spacious house nestled within an amazing wooded area. We had the pleasure of waking up to all the trees covered in fresh snow. All the more perfect because the house has huge windows lots of natural light. Highly recommend.

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What guests are saying

Beartopia- hot tub, views, 2 primary suites!

5 out of 5 average rating, 32 reviews1 month ago

We loved our stay here, I have only great things to say. The house was perfect for our group of 8. The access to the mountain and to town is super easy, and everything about the house is as good as it looks in the pictures. Dan/Holly had great communication leading up to and throughout our trip. I’d highly recommend staying here.

Home in Killington

What guests are saying

Ski-in Ski-Out Cozy Mountainside Condo

4.88 out of 5 average rating, 57 reviews4 months ago

Everything was lovely. The house was warm and cozy. We so enjoyed gathering around the fireplace in the evening. Just 10 minutes away the kids went skiing at the Quechee Ski Resort which they liked and was so accessible. Last but not least our host Robin was so nice. She answered all our questions immediately. And was very pleasant.

Townhouse in Hartford

What guests are saying

Private post & beam log cabin on Macintosh Pond.

4.8 out of 5 average rating, 15 reviews3 months ago

It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!

Cabin in Barnard

What guests are saying

Gigi and Pops' Secret Cabin

5 out of 5 average rating, 55 reviews3 weeks ago

Wow! What a spot! Not only is the house amazing, the property is also amazing! The location is 10 min from town and 10 minutes to the mountain! The house was very clean and the owners thought of everything that you would need! We brought our 4 young kids and between the fort outside and the playroom, they had the best time! We will definitely be back!

Home in Chittenden

What guests are saying

The Carol

5 out of 5 average rating, 22 reviews1 month ago

The Carol is a stunning and beautifully decorated historic home that was the perfect getaway for our ski trip!!! We stayed one night but wish we had stayed longer! It is located only 10 mins from Okemo which was perfect. The beds were super comfy and the bathroom and kitchen were stocked with everything we needed. Sarah was super helpful and responsive to everything and provided tons of recommendations to make our stay worthwhile. Would 100% recommend this place to anyone looking to ski Okemo!

Home in Cavendish

What guests are saying

Hilltop 4-BR Retreat 8-min to Okemo Mountain

5 out of 5 average rating, 8 reviews3 months ago

Stayed here with friends and family to snowboard at Okemo. Unreal Mountain View’s from the living room! Perfect location right down the road less than 10 minutes which was a game changer after a long tiring day. This place was better than I imagined and perfect for us. Three entry ways the mud room was great to drop all the gear. Kitchen had everything we could have wanted, probably the best and most thoughtful Airbnb. We cooked a lot and we didn’t feel like we were missing anything we needed! Plenty of books and board games.. scrabble and chess won the favorites of our group. Water got hot quick for showers. Fireplace really warms the place up quick. Host left a personalized handwritten note to us and messaged us during our stay if we needed anything. We would all happily make another trip and come back! If I had to say one thing it would be that some of the beds and pillows weren’t as comfortable but it wasn’t a deal breaker! Place exceeded our expectations!!

Home in Ludlow

What guests are saying

Luxury Modern Cabin near Okemo & Killington

5 out of 5 average rating, 16 reviews1 month ago

Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!

Home in Plymouth

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Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Popular amenities for Windsor County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Windsor County

5 out of 5 average rating, 35 reviews

A distinctive architectural home is surrounded by lush greenery, featuring a unique sloped roof that adds character. A pathway lined with gravel leads to the wooden deck, where seating is visible, offering a tranquil outdoor space with views of the mountains.

Home in Stockbridge

Unique Mountain Retreat

RaymondRating, 5 stars1 month ago

Great place to stay. Agnes and Roger were great hosts. House was spotless and clean.

4.85 out of 5 average rating, 249 reviews

An inviting living area is highlighted by a stone fireplace, surrounded by wooden walls and a peaked ceiling. A cozy seating arrangement includes a leather couch and two footrests, while a small table holds a lamp. Windows offer glimpses of the outside ambiance.

Cabin in Mendon

THE CABIN....a Vermont log home

JeffRating, 5 stars1 month ago

Bill's cabin was excellent. Rustic and rural but close to Killington and Pico, and a quick ride to Rutland. It was clean, comfy and had all we needed for a great little stay. It got a thumbs up from my wife and that is a high standard to meet. She even liked the king bed so much she was looking for the label to get one like it for home. I'm a guy and don't need much. The cabin made me feel like I was staying at a friend's house. You can nit-pick about the lighting and other minor stuff, but to me this place was a 10 out of 10 stars. We may be back next year for a longer ski vacation. Thanks Bill.

4.75 out of 5 average rating, 92 reviews

An outdoor pool is surrounded by lounge chairs and red umbrellas. Lush green trees frame the space, creating a serene environment. A small poolside shed is visible, adding functionality to the area.

Condo in Killington

Still 89 Trails Open, Low, Low Rates

RyanRating, 5 stars1 month ago

Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.

4.84 out of 5 average rating, 88 reviews

The spacious living area features a stone fireplace flanked by comfortable seating arrangements. Large windows provide natural light, creating a warm atmosphere. A wooden mantle is adorned with decorative skis, while a coffee table complements the seating. Light fixtures add a soft glow to the room.

Home in Killington

Killington Racquetball House

EmersynRating, 5 stars3 weeks ago

This was our second time staying at the racquetball house and it was just as incredible as the first. Lucked out with some great spring skiing on Friday, and checked into the Airbnb after. The house is very conveniently located to the mountain. We made full use of the court. Played racquetball, volleyball, dodgeball, kickball, pickleball, wall ball. Basically just spent all weekend playing games in the court and then relaxing in the hot tub to end the day. The living room / kitchen area is a great gathering layout. We will definitely be back.

4.92 out of 5 average rating, 25 reviews

The exterior view showcases a classic cape farmhouse surrounded by lush greenery. A patio area is visible, featuring stone pathways and manicured gardens. The house features large windows allowing natural light and a glimpse of the private swimming pond in the background.

Home in Woodstock

Great Maples

CatherineRating, 5 stars2 months ago

We loved our stay at Great Maples and are already thinking about booking another trip. We shared the house with another young family, and it worked out great. Plenty of space, clean, and beautiful. Private and relaxing but also lots of fun activities in neighboring towns. It even had a playroom and lots of books and toys for our kids. We can’t wait to go back!

4.96 out of 5 average rating, 53 reviews

The interior of a Scandinavian outdoor barrel sauna is visible, featuring wooden benches positioned along the walls. A small stove is located at the center, with a wooden bucket and ladle placed nearby. A large round window offers views of a green landscape and distant mountains.

Home in Chester

Farmhouse w/ views close to skiing sauna EV CHRGR

NicaRating, 5 stars1 month ago

My friends and I had a great time at this airbnb. Miguel was very responsive and helpful when we needed help with the WiFi. The place was exactly like the picture and very peaceful! The kitchen was fully stocked. Highly recommend staying at this airbnb.

5 out of 5 average rating, 8 reviews

A warm hot tub is presented against a snowy landscape, surrounded by trees bare of leaves. The distant view of the reservoir is framed by the serene white of winter, inviting relaxation and tranquility.

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

MaddyRating, 5 stars2 months ago

I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!