Places to stay in Windsor

4.92 out of 5 average rating, 12 reviews

Home in Hartland

A quiet x in VT to Ski, Hike, Hot tub~3m Quechee

XanderRating, 5 stars1 month ago

I visited Thatcher and Lisa's place for a few days in February with 5 friends. It was an incredible experience overall. The home was a perfect peaceful getaway, with awesome amenities like multiple private rooms, a well-stocked kitchen, hot tub, and games. It is also very nicely located, providing a peaceful rural setting while also having great access to nearby areas like Woodstock, Hanover, and Killington (where we spent ~3 days skiing). Additionally, Lisa and Thatcher really went above and beyond as hosts. They left very clear instructions and recommendations, made sure that we arrived smoothly in the face of inclement weather, and even shipped home an item we left behind. I definitely recommend staying here for your next Vermont adventure!

4.97 out of 5 average rating, 88 reviews

Apartment in Pittsford

THE FERN: Relax in peaceful Vermont country

AndrewRating, 5 stars6 months ago

We came up for a little fall vacation to explore the local area and could not have found a better place! Absolutely beautiful location with a perfect sunset, fantastic hiking right behind the location as well. Gerd and Gisela were communicative, friendly and had really good local recommendations for spots that highlighted the trip. If I could give more stars I would

4.97 out of 5 average rating, 32 reviews

Townhouse in Hartford

Windfall at Quechee Lakes VT~ Ski -Golf -Explore

JoyRating, 5 stars3 months ago

The condo was everything we wanted and more! Kat has made the condo feel so homey and comfortable. She left amazing touches like a cute sign to great us, clear instructions and recommendations, and extra items like robes (amazing)! She was super responsive and helpful! The condo is large and comfortable with great views of trees and the river. It was the perfect location to ski, and visit Dartmouth, and the Upper Valley. I wouldn’t hesitate to stay again!

5 out of 5 average rating, 10 reviews

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!

4.75 out of 5 average rating, 4 reviews

Chalet in Dover

Relaxing Retreat in the Heart of Dover

LauraRating, 5 stars2 months ago

We stayed here for our annual family ski trip. The house was a perfect size. There was 11 of us and plenty of space. The house was clean and decorated nicely. Big kitchen. The kids loved the hot tub. Mt Snow was 5 minutes away. They answered all of my questions fast. Check-in was easy. The check-out instructions were clear. Close to shops and restaurants. We plan to stay here again next year. Highly recommend this house for a family or friends getaway.

4.95 out of 5 average rating, 147 reviews

Cottage in Woodstock

The Cottage on Westerdale Road

IreneRating, 5 stars1 month ago

The house was clean and tidy. Barbara was a lovely and very responsive host. When a couple issues arose, they were dealt with in a very expedient manner. The location of the home could not be beat - great proximity to Woodstock, Killington/Pico, and Saskadena. We enjoyed our stay very much.

4.93 out of 5 average rating, 14 reviews

Home in Rutland

Comfortable Vermont Getaway. Three bedroom home.

KevinRating, 5 stars2 months ago

Robyn and her family are great hosts. She and her son were there when we arrived shoveling the drive way, gave us some helpful tips about the house, very friendly and accommodating - we were able to check in a couple of hours early and really made us feel right at home. Beautiful house with all amenities: Kitchen had everything would need to cook for several days (pots, pans, utensils, glass/coffee mugs, and even provided coffee and filters) - we only needed to bring food to prepare. Stores were close by and easy to get to. Bathrooms were pristine with plenty of towels and toiletries, bedrooms were spotless and comfortable, and had a great fireplace that was very useful during some cold days. About 15-20 minutes to Killington Mountain - easy drive. Fantastic property and we had an amazing stay, would definitely come back!

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What guests are saying

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

5 out of 5 average rating, 10 reviews3 weeks ago

There is not a shortage of things to do at Anthony's place. The game tables, sauna and hot tub made the weekend really fun, especially for the non skiers of the group. The view from the house is also spectacular! We would definitely rent this place again.

Home in Wilmington

What guests are saying

Killington Retreat - ❤️ of the Green Mountains ⛷

4.84 out of 5 average rating, 44 reviews1 month ago

Jaclyn's place was perfect for our ski trip to Killington. It was an easy and quick drive to the mountain each morning. And, we enjoyed cooking and relaxing at the condo when we returned in the evening. Very convenient to have laundry capabilites and the ambiance of the fireplace was fantastic. Jaclyn was a delight to communicate with. We highly recommed her place!

Townhouse in Killington

What guests are saying

Okemo Hot Tub Fireplace Billiard

4.93 out of 5 average rating, 67 reviews1 month ago

Our stay was awesome! The driveway was icy but the hosts provided salt for us to use and the snow-pile guy came during our week and spread sand which was very helpful. The house was huge and provided lots of activities and room for everyone to spread out. We had some amazing family dinners using the well equipped kitchen and large dining space.

Chalet in Mount Holly

What guests are saying

Harrisville Lake House - A Tranquil Get-Away

4.9 out of 5 average rating, 10 reviews6 months ago

I’m grateful that Peggy and Harry were willing to rent to us at the last minute. Our family needed a quiet respite to be together during a difficult time of loss. The solitude of the lake and woods was calming and we had plenty of room to be together. I only wish we could have stayed longer!

Home in Harrisville

What guests are saying

On the Water at North Bridge Cove

4.96 out of 5 average rating, 28 reviews1 month ago

Nice little spot. The bed is very comfortable and the shower has good pressure. I only interacted with Jon once at which time he was pleasantly helpful. The sauna was an excellent addition and very much appreciated. The only complaint I have is that there isn't a comfortable seat to relax in. It's not a big deal. I would stay here again.

Cottage in Brattleboro

What guests are saying

Upper Valley Shaker-Style Home, close to Dartmouth

4.95 out of 5 average rating, 19 reviews5 months ago

Barbara's place is a real gem. So clean, with a beautiful mix of antique and woodsy modern furniture, and a wonderfully comfortable living area overlooking a meandering brook which a few hundred yards down the road leads to the lake. The kitchen was well-equipped and modern, and beddings and beds were very comfortable. While the house was close too a busy road, we didn't hear a thing, and for summer users the deck is completely away from the road, overlooking the brook. Even more than we expected.

Home in Enfield

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Popular amenities for Windsor places to stay

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Laptop-friendly workspace

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Stay near Windsor's top sights

Harpoon Brewery Taproom and Beer Garden125 locals recommend

Saint-Gaudens National Historical Park62 locals recommend

Windsor Station Restaurant & Barroom33 locals recommend

Brownsville Butcher & Pantry32 locals recommend

Cornish-Windsor Covered Bridge28 locals recommend

Price Chopper27 locals recommend

Other great vacation rentals in Windsor

5 out of 5 average rating, 8 reviews

Home in Bellows falls

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars2 months ago

We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!

4.86 out of 5 average rating, 35 reviews

Home in Manchester

Your VT Dream House: Fireplace, Pool, Dogs

AtulRating, 5 stars8 months ago

Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.

4.91 out of 5 average rating, 11 reviews

Home in Dover

Amazing Family getaway!

KerriRating, 5 stars1 month ago

This house was a great spot to stay in between days of skiing. Everything was clean and comfortable.

5 out of 5 average rating, 8 reviews

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

MaddyRating, 5 stars1 month 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!

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.

4.81 out of 5 average rating, 133 reviews

Home in Tinmouth

Vermont Lakefront Getaway "The Wild Loon"

WilliamRating, 5 stars1 month ago

The place was perfect for our winter family vacation. The home was as described in a beautiful setting with a great view. If staying in the winter months having a vehicle with at least all wheel drive is helpful, as this is Vermont. The home is out of the way, but easy driving distance to ski and explore the nearby towns.

4.88 out of 5 average rating, 105 reviews

Home in Wilmington

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

JamesRating, 5 stars1 day ago

Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.