
Vacation rentals with outdoor seating in Brattleboro
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Top-rated accommodations with outdoor seating in Brattleboro
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 Brattleboro outdoor seating rentals
House rentals with outdoor seating

Sunny Sunapee Retreat (Upstairs Only)
Julie's place is so close to Mount Sunapee and the Lake! It is wonderful on the inside and has plenty of room for guests. It is also close to a couple great food options. This house is a great place to stay.

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.

2.5mi from the lake! Fire pit, arcade, yard games!
Great spot! Stayed at Eric's place for a weekend with a group of college students (8) looking to hit the reset button and had plenty of space. It was spotless and comfortable, and we had no trouble finding what we needed. The virtual guide is also super helpful!

Summer & Leaf Season Rental!
What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

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.

MtSnow * HotTub * Pool * Air Hockey * 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.

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!

Hudson River Valley/Berkshires
I use AirBnB 3-4 times per year since many years. Frankly this is the most welcoming, best appointed, better layout place I've been. There is absolutely nothing missing here, in the kitchen or bathrooms or at overall comfort. There are multiple living areas which means that if you go with 4-6 people everyone can find privacy if needed. Great place, we'll definitely be back.
Apartment rentals with outdoor seating

Light filled three bedroom apartment DT Florence!
I chose to stay at Donna's a second stay because I appreciate the quiet neighborhood and very, clean comfortable home. Communication with Donna is easy and friendly.

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!

"Up Top” at Ro & Oak House
Such a wonderful AirBnb, and one of the cutest ones I've ever rented. Everything was spotless, and there were so many thoughtful touches -- from games and magazines, to a fully-stocked yoga corner, to comfy pillows and various bed linens. It really was the perfect spot, and I would love to visit again. It's walkable to downtown Keene, just a block or two from the town square. There are a lot of stairs to get up to the apartment, but the number-code locks make it easy to go in and out of the apartment and it felt very secure. Highly recommend. Such a beautiful home.

Suite 23 - Spacious Sunny 2-BR with Mountain view
We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

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.

River View Apt in Shelburne Falls Historic Village
Thanks Crystal It was a great spot for the weekend and very comfortable!

Quiet bright & sunny 2 bedroom apartment w/ porch
It was a great experience, very easy to get to.Super clean we enjoyed our stay!!

Tree Top Suite, cozy downtown apartment
Susan’s place was lovely! We had a very nice stay for my sister’s wedding. The bathroom is so big and beautiful! Thank you :)
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.

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!!
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- Stratton Mountain
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Pineridge Cross Country Ski Area
- Ekwanok Country Club
- Hooper Golf Course
- The Shattuck Golf Club
- Baker Hill Golf Club
- Bousquet Mountain Ski Area
- Canterbury Farm
- Stump Sprouts Ski Touring Center
- Northern Cross Vineyard
- Clarksburg State Park
- Hancock Shaker Village
- Hildene, The Lincoln Family Home
- Dorset Field Club