
Vacation rentals with outdoor seating in Dorset
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Dorset
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 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.

KATERINA OF OLD SARATOGA
We were looking for a place to host a memorable family Christmas when I found Vasili’s home, and it couldn’t have been more perfect. The home is vast yet full of charm and it was spotless upon check-in, which was a breeze thanks to Vasili’s seamless and helpful communication. The house itself was so warm and inviting but the crown jewel of the space was the massive and incredibly well appointed kitchen! We love to cook (a necessity for a quality family gathering) and Vasili’s kitchen had everything you could ask for! Including a restaurant grade dishwasher (8 minutes per cycle) and a massive r we strains grade fridge/freezer combo. Tons of counter space.. every kitchen tool you could imagine… tons of dishes and cups… a full wet bar with an ice machine… it was amazing! Thank you so much for hosting us Vasili! Can’t wait to be back in your beautiful home!

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
Christine was an amazing host - her home is beautiful, well furnished and felt so cozy! Lots of linens and blankets and it was decorated beautifully for the season. We were greeted with a personalized welcome envelope, plus some local treats, and wine/cheese plus some grocery staples in the fridge. Her instructions were clear, easy to follow and she was very proactive/responsive during our trip communicating with us. Absolutely LOVED our stay here and highly recommend if you’re looking to visit the Brattleboro, VT area. One of the best B&B stays we have had - look forward to coming back!

Close- > MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
The place was amazing. It was what the pictures show plus much more. Me and 10 of my friends slept comfortably and had a great time. Many games, nice kitchen, clean rooms and bathrooms, and if you’re a winter lover, hope it snows because this yard is amazing. We went sledding like kids again it was great. Definitely recommend. Right near mt. Snow and town of Wilmington which has great food options. Overall, quite the memorable stay.

Luxury Contemporary Home - Minutes to Stratton
What a view! Walked into a beautiful space filled with light. Big open modern kitchen next to a great hang out space with pool table and dining table. Nice bedrooms with big updated showers. Loved the hot tub and sauna. Wonderful cozy place to wake up in and come home to after a fun day of skiing.
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
This is a clean and cozy in-town top floor apartment - within walking distance of Main St, the Brattleboro Food Co-op and many local eateries, coffee shops and excellent shopping opportunities. The apartment is nicely decorated, and we loved the closed in sun-porch for gearing up to go outside since this was mid-winter during a cold snap.

Apartment with a view
I had a great experience staying here! I booked it last minute, and it turned out to be a perfect choice. The space was comfortable and had everything we needed for a pleasant stay. The area was quiet, making it easy to relax. The host was also very responsive and accommodating, which made the whole experience smooth and stress-free. I would definitely stay here again!

Globetrotter Retreat too - Minutes to the Mountain
My wife and I had a great stay! Walking distance to the key shorts in Wilmington and a very short drive to Mt Snow!

River View apartment
Susan's place was very nice, clean and perfect for relaxing. Has everything you need for a comfortable stay.

Families, Pets, Coffee, Arcade, Foosball, Fire pit
This was my second stay at this location but 2 different units, and both were very nice. I can't wait for my next trip. looking forward to renting again

Sunny Troy Private Deck Parking Wi-Fi Top Floor
Centrally located right near downtown and close to major roads. Easy to find with the bright orange door and there was always available parking on the street close by. It was cozy and private.
Condo rentals with outdoor seating

Renovated unit, prime location! Shuttle on/Ski off
Caitlyn's place was perfect for our ski weekend at Killington! The unit is exactly as described and we felt right at home as soon as we arrived. We appreciated the ski shuttle access so we didn't have to worry about parking and being able to ski back on the access trail was super convenient. Wouldn't hesitate to stay here again!

Mount Snow Ski Chalet
Great stay and perfection location just off the base of Mount Snow with MOOver access. Mike was very responsive and accommodating for our last minute booking. Had trouble getting in with the code but he answered and helped us get in immediately. 10/10 host

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
James was a great host, the place was very clean and VERY close the the ski trail. Would love to stay again some day!

Winter Dream! The Handle Lodge at Snowtree Condos
Stayed over Presidents’ Day weekend with a total of 4 adult guests. Condo is perfect with everything you need. Extremely close to the Mount Snow ski resort and access to Moover Van. Rafael was available to us during our stay and was extremely helpful particularly when the weather got worse with a big storm. Would definitely recommend the condo but also to rent from Rafael and Janice. We ate at Snow Republic Brewery, Maple leaf Tavern, Saw Mill Bar and Table and Valley View Saloon. We highly recommend them all but note that Valley View Saloon has large portions.

Location + Spa! - Cozy 2BR Condo - Mountain Side
We had a great long ski weekend. Host is very communicative and helpful - with quick answers to any questions we had. Great spot for our family of 5. Easy to get to mountain. Very clean and comfortable rental! This was our second stay and we’d be happy to stay again.

Okemo Clock Tower Base Ski-in/Ski-out Condo
This was our second time staying here. Love the location and accommodations are clean and feel like home. Would definitely come again!

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.

Serene Top Floor Condo (resort style amenities)
Scott is an outstanding host! His place is conveniently located next to the ski slopes, and he was incredibly responsive to any questions we had. Highly recommended!
Quick stats about vacation rentals with outdoor seating in Dorset
Total rentals
40 properties
Nightly prices starting at
$58 CAD 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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