House vacation rentals in Windsor County

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Popular amenities for Windsor County house rentals

House rentals with a pool

Guest favorite
Home in Killington
4.91 out of 5 average rating, 202 reviews

Luxury Condo Tucked in the Heart of Killington

AshleyRating, 5 stars2 weeks ago
Comfortable and convenient location. Everything we needed was in the kitchen. We had most of our meals in and took advantage of the kitchen. The sleeping accommodations were very comfortable. It is only a short drive to Killington, where my family skied. We would definitely stay there again.
Top guest favorite
Home in Mendon
4.89 out of 5 average rating, 245 reviews

Ranch at Mendon Mt Orchards

StephanieRating, 5 stars1 week ago
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!
Top guest favorite
Home in Rutland
5 out of 5 average rating, 10 reviews

Entire Home, Near Slopes, Hot Tub, EV Charger

MicahRating, 5 stars1 month ago
The stay was excellent. The home was beautifully renovated. The rooms were large and very comfortable. Location was perfect for the 8 of us for a ski weekend at Killington. Hope to be back.
Superhost
Home in Hartford
5 out of 5 average rating, 25 reviews

The Fairway House - Premier Golf Course 3 BR Home

JanetRating, 5 stars19 months ago
We thoroughly enjoyed our stay with 5 adults and one dog. We walked in and immediately felt at home. This was one of the most well appointed places I have ever rented...it had everything we needed and more . The kitchen and the living space was quite comfortable. The beds were wonderful. There is a trail to the river right across the street which we used several times. I can't think of a negative thing to say.
Top guest favorite
Home in Hartford
4.92 out of 5 average rating, 38 reviews

Bright & Modern Quechee Town House - Self Check-In

GailRating, 5 stars1 month ago
We loved it! Great description and photos, really accurate. Michael was so helpful and really friendly and responsive.
Guest favorite
Home in Hartland
5 out of 5 average rating, 10 reviews

Private Farmhouse with in ground pool!

ChrisRating, 5 stars7 months ago
My family and I truly enjoyed our time spent at the farmhouse. Everything was as expected from the listing. The pictures do not do justice for the property. It's beautiful and well maintained. The pool was nice, warm, and clean. There are yard games readily available and a nice fire pit area. Brin and Maria are super responsive and left very detailed instructions on the property for you. Everything you need is there minus food, which is a 12-minute drive towards a few different grocery stores. The hill is so fun to roll down, too! Thank you so much!
Superhost
Home in Landgrove
4.75 out of 5 average rating, 8 reviews

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths!

ShanleyRating, 5 stars3 months ago
we arrived late in the evening and was amazed at the size of the house. I was lost a few times as it has several staircases and several ways to get to the kitchen and pub area. The kitchen is well stocked, many pots and pans. All the tools you need. Also a very large stove and oven. Brand new fridge, a chefs work table and a separate dinning table for 8 or 10 people. Chefs delight. Plenty of dinnerware! The solarium was my favorite room morning and mid-day. Sunshine through the snow covered pines, very beautiful! Gas fireplace made it very cozy! In the evening we enjoyed the Pub area. Played ping pong, pool and watched some movies. Wood burning stove was very warming and pleasant to watch! Everyone slept well, and each bedroom had their own bathroom with a soaking tub. We really enjoyed Okemo, Magic mountain, the local farm stores and the Scottish pub MacLomains, friendly staff and great beers and food! Hope to return next year!
Guest favorite
Home in Chittenden
4.91 out of 5 average rating, 89 reviews

Comfortable, relaxing large country home

EdwardRating, 5 stars2 months ago
Great spot for a week of skiing! Danielle was very helpful and communicative throughout

Weekly house rentals

Superhost
Home in Ludlow
4.83 out of 5 average rating, 12 reviews

Hilltop 5-BR Carriage House 4-Min to Okemo

KelseyRating, 5 stars15 months ago
Meadow’s place is beautiful. It’s modern, homey, and super cozy. Everything was clean, the location was less than 5 min from town shops & Okemo Mtn. The beds were incredibly comfy, the house was spacious, and the bathrooms were spotless. There is also a jacuzzi in the back that was very clean and kicked on frequently. 10/10 would recommend this property. We will definitely be back!
Superhost
Home in Chester
4.8 out of 5 average rating, 94 reviews

Vermont 1828 Reunion House, sleeps 16, near Okemo

FaytheRating, 5 stars2 months ago
We absolutely loved our stay at the Reunion House! The home was cozy and charming, and Margaret was a great, responsive host. She went above and beyond to be accommodating for us during a massive snowstorm and made sure we had everything we needed during our stay. We would love to return!
Guest favorite
Home in Killington
4.9 out of 5 average rating, 71 reviews

Game Room + Hot Tub - 7BR updated home

AlexRating, 5 stars1 month ago
We had a great stay at Michael’s place! The house was lovely with room for all 16 of us both in common spaces and beds. One of the best parts about this stay is the proximity to Killington and Pico Ski Resorts - it is genuinely <15min from both mountains! The hot tub was also fantastic and made our trip. One small word of advice would be during spring ski season to make sure to bring footwear that can get muddy for the parking areas next to the house. Other than that, our stay met and exceeded all expectations!
Superhost
Home in Cavendish
4.8 out of 5 average rating, 71 reviews

OKEMO MT HOUSE - OKEMO-LUDLOW-JACKSON GORE

RobertRating, 5 stars2 months ago
House fit our need was a good location for skiing at Okemo
Superhost
Home in Bridgewater
4.86 out of 5 average rating, 125 reviews

Blueberry Hill Escape Pet Friendly HotTub Fire pit

BrianRating, 5 stars5 days ago
Chris isn't joking that he likes to keep the kitchen well stocked. It was great having everything that a typical kitchen would have at your convenience. The views were gorgeous and were really enjoyable when relaxing in the hot tub. Our three boys loved the kids room and that there were toys to play with. The location made our Vermont stay all that much more enjoyable, thank you for the great memories!
Guest favorite
Home in Clarendon
4.96 out of 5 average rating, 291 reviews

Killington Retreat | Deck-Fire Pit-Mountain Views!

Pradeep BabuRating, 5 stars4 days ago
Jeff was an awesome host. He shared the instructions to get to the house and all things to do around the house. Followed up with us once we got there about our experience to check in and made it very easy for us. The house is great and we enjoyed every bit of it. The best place is the deck overlooking the mountains. We did lot of grill and enjoyed eating on the deck. Kitchen was pretty well organized with all the utensils and literally everything was available, even if we missed carrying few things from home, it would have been available at the house. Kids enjoyed board games and watching TV. Best experience we had in recent times.
Top guest favorite
Home in Hartford
4.97 out of 5 average rating, 103 reviews

Luxury Barn Home w/Hot Tub, Sauna, Gardens MtnView

DianeRating, 5 stars3 months ago
This is my second time staying at Hilary’s home, and for good reason! My family loved gathering by the fireplace everyday, using the hot tub and sauna, and cooking dinners for our group of 8 in the well equipped kitchen every night! Plenty of room for us to spread out. Also love how close it is to the town of Woodstock (adorable with great shopping!) Hilary is very responsive and I am sure we will be back for a 3rd time at some point.
Superhost
Home in Rutland
4.81 out of 5 average rating, 155 reviews

6 Bedroom Home Mendon, VT. (Killington/Pico)

SuzanneRating, 5 stars1 month ago
This is our third (or fourth?) year staying here and they keep adding little things to make it better. Host is very responsive. House matches the description, and the price is right! Plus we were able to add another night onto our stay at the last minute which was really helpful.

Private house rentals

Guest favorite
Home in Clarendon
4.86 out of 5 average rating, 29 reviews

Peaceful Vermont Mountain Cottage -Pet Friendly!

CraigRating, 5 stars1 month ago
The house was perfect and Nicole was a fantastic and responsive host
Superhost
Home in Ludlow
5 out of 5 average rating, 18 reviews

2 Units, 1 Home | Perfect for Multiple Families

QiningRating, 5 stars1 month ago
The overall experience is good. Just a reminder: the 1st and 2nd floors use separate doors and are not internally connected. However, the location is very close to Okemo and Killington, and the interior decoration is quite good for the price.
Top guest favorite
Home in Rutland
5 out of 5 average rating, 57 reviews

Hot tub, Killington 15 min drive, 3 beds 1 Bath

JessicaRating, 5 stars1 month ago
This charming home was an absolute gem, offering the perfect retreat for four parents on a ski weekend. Warm, cozy, and inviting, it provided every convenience we could possibly need—even an outdoor grill. The hot tub and outdoor space were especially delightful, with thoughtful touches like ski-themed benches and a fire table creating a welcoming ambiance. The addition of bathrobes for the hot tub was a lovely detail that made our stay even more special. Communicating with Dennis was seamless, and his hospitality stood out. If we find ourselves in the area again, we would undoubtedly return to this well-appointed and thoughtfully designed property!
Guest favorite
Home in Fairlee
4.95 out of 5 average rating, 238 reviews

The Upper Valley Retreat

PeterRating, 5 stars3 weeks ago
We had 17 teens and six adults on a church teen retreat. Great accommodations with plenty of beds for all of us. Nice large kitchen to cook for everyone. Huge refrigerator to hold all the food. Nice large living room for us to all meet in and hang out. The kids loved the pool table. We all enjoyed our stay very much.
Superhost
Home in Killington
4.84 out of 5 average rating, 88 reviews

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.
Guest favorite
Home in Killington
4.94 out of 5 average rating, 117 reviews

Cozy Private House on Killington Mtn - Hottub

MeganRating, 5 stars1 month ago
This airbnb was even better than we expected! It is just minutes away from all the Killington lodges and the restaurants/bars in town. The house was extremely clean, easy to find, and perfect for a group of skiers. I highly recommend it for anyone looking for a beautiful, easy place to stay at Killington. Would love to stay here again next time we visit! Highly recommend.
Guest favorite
Home in Rochester
4.98 out of 5 average rating, 203 reviews

The Guest House at Sky Hollow

MargaretRating, 5 stars3 months ago
The house more than met our expectations! We skied at Killington and Sugarbush and snowshoed on trails behind the house. The house was very cozy and quiet with a large kitchen and very cozy spots to read and sleep in after a long day of being outside. I highly recommend staying here!
Guest favorite
Home in Plymouth
5 out of 5 average rating, 9 reviews

Snowledge II by Okemo/Killington

GiannaRating, 5 stars2 months ago
Lovely stay!!! She’s not kidding about the AWD or 4WD. One of our cars couldn’t make it up the driveway after it snowed. Beautiful place with everything you could possibly need. The coffee machine really saved us. Thank you and would definitely recommend!

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