
Vacation rentals with outdoor seating in Cavendish
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Top-rated accommodations with outdoor seating in Cavendish
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Cavendish outdoor seating rentals
House rentals with outdoor seating

2 Master Suites, Hot Tub, Walking to Downtown.
Behind an unassuming exterior façade, the interior was truly remarkable from an interior design and furnishing perspective. Not only were the furniture, linens and glassware spectacular, The overall result was a beautiful and tranquil retreat. We were super impressed and would love to return.

Spacious Brattleboro home on river, walk to town
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

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

The River House
We had a lovely time at this place, it’s a bit small but we’ll appointed and you can’t beat the location, right on the river! The views out the back were incredible every day. This didn’t impact us but be aware the upstairs loft area is probably better for children and a tall adult would feel pretty cramped up there. As a rather short crew my family had no problems 😂. Would definitely stay again.

Modern Spacious Home with Mountain Views
My family of four loved Christine’s place! She is so thoughtful, leaving yummy snacks plus necessities as well. She’s a great baker and provided us with some yummy treats! The beds were super comfy and cozy, bathrooms were clean and well-equipped and we loved being both close to downtown but also could go hiking out the back door. We feel so grateful to have had such a lovely and relaxing place to stay. Thank you, Christine! ❤️

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
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.

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 .

Private Field House - Spacious 4 Bedroom Home
Absolutely pristine and gorgeous home. We were constantly talking about how perfect it was the entire time we were there. Would definitely stay again!
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!

Quiet St in Town, gardens, terrace
We loved our stay at Jaki’s place! Very easy check in, easy to find, no issues at all. Very comfortable place and walkable to downtown. Would definitely stay here again!

Apartment with a view
The quintessential Vermont Airbnb! Beautiful surroundings, lots of outdoor activities, and easy to get into town with great restaurants. The hosts are very helpful and provide everything needed for a relaxing stay.

Globetrotter Retreat too - Minutes to the Mountain
Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

River View apartment
Susan’s place was quiet, clean and lovely. Close to town, but still in a wooded area. The apartment is well designed with everything you could need, including delicious coffee.

Cozy Apt. Near heart of Middlebury Fiber WIFI
My daughter and I had a great time. We were able to bike several times straight from the house, and the town had everything we needed for a local run, food shopping, and restaurants. It was a perfect little getaway!!

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!
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 vacation rentals with outdoor seating in Cavendish
Total rentals
40 properties
Nightly prices starting at
$124 CAD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- 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
- Fort Ticonderoga
- 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
- Crotched Mountain Ski and Ride