
Vacation rentals with outdoor seating in Dorset
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Top-rated outdoor seating rentals in Dorset
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Popular amenities for Dorset outdoor seating rentals
House rentals with outdoor seating

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

Ranch retreat
This home was exactly what I was looking for. The home is perfect size for a family of 5 with 3 teenagers. Perfect location for our family from the “country” it was in the perfect location with a cute little store within walking distance if needed. Everything was as described. We will be back in the summer and yearly for the winter carnival. Thank you for all the recommendations as well.

Cheerful, quiet 3 bedroom home
Our hosts were very easy to work with. I felt they cared about our visit and wanted to accommodate us in any way that would make her stay even more pleasurable. The house offered every convenience, including kitchen items for make-at-home meals. Thanks so much, Brandon and Brian!

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.

Central Haus (Group getaway on a quiet street)
Our group of friends loved staying in this comfortable, very convenient spot for a weekend of relaxing and visiting MassMoCA. The street is quiet and still very close to center of North Adams. We visited during a snowy weekend but would be nice to return in warmer weather to take advantage of nice backyard and fire pit.

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 * Air Hockey * PingPong * Darts
⭐️⭐️⭐️⭐️⭐️ Amazing Stay with Wonderful Hosts! Our stay at Matt and Diane’s place was absolutely fantastic! From the very beginning, they were incredibly kind, welcoming, and helpful, ensuring we had everything we needed for a smooth and enjoyable visit. Their communication was excellent before, during, and even after our stay, making us feel truly taken care of. The property itself was exactly as advertised—spotlessly clean, well-equipped, and stocked with all the amenities we could ask for. It was the perfect place to relax and feel at home. Their attention to detail and hospitality made all the difference. I would highly recommend this property to anyone looking for a comfortable and stress-free stay. Thank you, Matt and Diane, for being such amazing hosts—we can’t wait to come back!
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!

Village Apt #1 - walk to everything!
We had the best stay at Katelyn’s home and the location of this Airbnb TRULY cannot be beat!! We could not have asked for a better location, better amenities, check in/out experience, and communication with the host. Every touch was so thoughtful - we so appreciate the step stool in the bathroom for our toddler! Highly recommend!!

Quiet St in Town, gardens, terrace
A lovely stay with a welcoming host. We were in and out of town for a weekend and Jaki communicated wonderfully and made coming, going and staying so easy. Many thanks!

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
This property is definitely within the top five Airbnb’s that I’ve ever stayed at! The apartment is absolutely beautiful with no detail missed. The kitchen was impeccable with light snacks provided and coffee/creamer, which is a huge plus for me. The bathroom was spotless with beautiful, plush towels and a lovely washer and dryer set. The living room was very comfortable with a reclining couch. The bed was very comfortable with plush linens. I can’t wait to stay again when I’m working in town.

Families, Pets, Coffee, Arcade, Foosball, Fire pit
Great weekend stay here. Clean big and literally everything you could ask for! Thank you so much for hosting us!

Sunny Troy Private Deck Parking Wi-Fi Top Floor
This is a great place, and I experienced very helpful communication and a restful stay. Would consider this location and Susan’s others in the future!
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 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
Very clean and great location. It was about an 8 minute walk to the Ramshead lodge and we ate at two restaurants within a 5 minute walk. The shuttle was also easy and ran frequently. Would recommend!

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.

Great 2 bedroom condo at Stratton Mountain
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

Ski, Ride, Walk On/Off Condo On Pico at Killington
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.
Quick stats about vacation rentals with outdoor seating in Dorset
Total rentals
40 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
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- Pico Mountain Ski Resort
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