
Holiday rentals with outdoor seating in West Windsor
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Top-rated Holiday Houses with Outdoor Seating in West Windsor
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Holiday House Rentals with Outdoor Seating

Private cozy 2-bedroom, short drive to town
Thank you to Leif and the family for a great stay! Leif was a fabulous host, being very helpful and responsive. His wife was also very nice and shoveled out the walk way for us. The place was just as described in the listing. Comfy beds with easy access to the ski way. Thanks Leif!

Home Sweet Home
We enjoyed our stay immensely! We visit Rutland often and will continue to stay here as long as it is available! Everything was better than anticipated!

Grange Hall, South Woodstock Historic Home
We have the loveliest time and can’t wait to return. Thank you for being so helpful and responsive

Magic Creek
Cute Vermont farmhouse that had everything that you needed. We enjoyed Cooking inn and hanging out in the living with the fireplace. The hot tub was so much fun after a cold day on the mountains. There is a cute little coffee shop and super market only 10 minutes away.

Modern Summer Chalet with Lake Access, Kayaking
Alex's place was the prefect stay. We went skiing at Pats Peak and was conveniently located close by. Having a full kitchen was extremely helpful to cook breakfast in the morning. The house was comfy and cozy. Would definitely stay again!

Quiet lakeside retreat with private dock.
It was a great two week stay.. I enjoyed being at this lake house. The lake is across the road, and pretty to look at on the balcony. The clear view of the lake walking and driving in the morning was very peaceful. His dock is the nicest in comparison to his neighbors. Kitchen was very well equipped, top notch washer and dryer, excellent lighting , beds and linens were comfortable, couch was large, easy to sprawl out and take a nap. Michael was available and easy to communicate. The high reviews are true, he cares and is thoughtful . I look forward in future stays .

1800’s Farmhouse in Historic Manchester Village
A great option for a ski getaway! This house is conveniently located and only a short drive to Stratton Mtn. There is a wonderful great room with a cozy fireplace and a kitchen that suits all cooking needs. Lots of property for your dog to run too! Bundle up, some areas of the house were a bit chilly. You will feel like you’re staying in a piece of history as the house has a very old but charming way about it!

Relaxation|Hot Tub| Sauna|PingPong|Wood Stove!
A very comfortable and peaceful getaway. Everything we possibly needed was available. And, Alan is incredibly responsive.
Apartment rentals with outdoor seating

Lovely 2 Bedroom Apartment w/deck & pond view
This rental was perfect for our family’s overnight ski trip to Okemo. We have two teenaged sons who shared a bedroom. The kitchen had everything we needed to cook breakfast and (most importantly) to meet the AM caffeine needs. The rental was approximately 10 minutes away from Okemo, which was the best part for us. Already planning next February’s ski trip!

Newly Renovated Cozy Studio Private Apartment
Vinny was incredibly responsive, helpful, and flexible. The location was perfect for skiing Sunapee and the space was very warm, cozy and private.

White Mountain Log Home Retreat
A very kind couple and a lovely home. We had a winter storm come through at the end of our stay and they were very accomodating of a late checkout if we needed some extra time to deal with the snow. Also their hommade Banana bread is a 10/10!

Okemo Vermont Getaway
Great spot right next to Okemo! The cabin was better than the photos, felt really homey and clean.

Charming & Peaceful Upper Valley 1BR Retreat
Very comfortable, quiet, & peaceful! Very much enjoyed our stay!

Two-Bedroom apartment in the Green Mountains
Dick and Dorothy are some of the most lovely, hospitable folks we have ever met and we feel so lucky to have gotten to know them through our extended stays at their apartment for the the last 5 winters. Hancock is a truly special community and the apartment is an excellent choice for anyone looking to visit the area. It is conveniently located, well-stocked, and delightfully quaint. We are already excited to return!

Vermont Getaway Apartment
This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!

Victorian Inn Apartment
beds comfortable. heating works well. everything works well.
Condo rentals with outdoor seating

Renovated unit, prime location! Shuttle on/Ski off
This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!

Mount Snow Ski Chalet
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.

Cozy Light-filled Condo in Charming Eastman
this condo is the perfect set up for our family! we had 3 adults staying, with a dog and a cat. there were three separate full bathrooms which helped a TON. everyone had their own area to wind down. we stayed for easter and were able to cook in the kitchen. Lyn was super responsive with any questions we had! we’re hoping to stay again next easter with Lyn!!

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!

Winter Dream! The Handle Lodge at Snowtree Condos
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Location + Spa! - Cozy 2BR Condo - Mountain Side
We had an amazing stay at this place! The location was perfect—just a short walk to all the incredible relaxation amenities like the pool, steam room, and sauna, which made our trip feel like a true escape. Going for a walk while taking in the views of the mountains were absolutely stunning and made every morning feel special. The unit itself was spotless and had everything we needed for a comfortable, short stay. The kitchen was well-stocked, the bed was cozy, and everything felt thoughtfully arranged. It was the perfect home base for exploring Killington and unwinding after a day of adventure. Would absolutely recommend and may come back during the Peak of the Snow Sport Season!

Okemo Clock Tower Base Ski-in/Ski-out Condo
We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

SnowCub Pets Indoor Pool HotTub Sauna Fireplace
This was our first visit to SnowCub at The Woods and it was comfortable and well-equipped. Holly and Dan were great hosts - responsive, thoughtful (loved the greeting gifts), and easy to work with. I already booked another trip for June!
Quick stats about holiday rentals with outdoor seating in West Windsor
Total rentals
20 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Rentals with a fireplace West Windsor
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- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Owl's Nest Resort
- Pats Peak Ski Area
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Hooper Golf Course
- The Shattuck Golf Club
- Dartmouth Skiway
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Bromley Mountain Ski Resort
- Brattleboro Ski Hill
- Santa's Land USA