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Vacation rentals with outdoor seating in Brattleboro

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Brattleboro outdoor seating rentals

House rentals with outdoor seating

Superhost
The image depicts a vibrant red house nestled among greenery, with two kayaks resting on the lawn. Adirondack chairs are arranged near a firepit, inviting relaxation. A shaded area is visible, along with a small shed in the background.
Home in Sunapee
5 out of 5 average rating, 4 reviews

Sunny Sunapee Retreat (Upstairs Only)

AaronRating, 5 stars26 months ago
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.
Top guest favorite
A spacious deck extends from the house, equipped with an umbrella and several chairs, providing a view of the encompassing greenery and mountains. The home's exterior features warm brown siding and solar panels on the roof, set against a bright blue sky.
Home in Brattleboro
4.94 out of 5 average rating, 122 reviews

Spacious Brattleboro home on river, walk to town

DebbieRating, 5 stars2 months ago
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.
Top guest favorite
A spacious two-story home is nestled among lush greenery, featuring a light pink exterior complemented by maroon shutters. A paved driveway leads to a double garage, while a well-maintained lawn and garden enhance the inviting atmosphere of the property.
Home in Whitingham
5 out of 5 average rating, 57 reviews

2.5mi from the lake! Fire pit, arcade, yard games!

JuliaRating, 5 stars1 month ago
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!
Top guest favorite
A light-filled living area features a comfortable gray sofa adorned with decorative pillows. A stylish coffee table sits in front, with a potted plant adding a touch of greenery. Two large windows provide views of the outside, and a TV is mounted on the wall.
Home in Great Barrington
5 out of 5 average rating, 6 reviews

Summer & Leaf Season Rental!

AnnieRating, 5 stars4 months ago
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!
Guest favorite
A charming exterior of the house is captured, featuring light-colored siding and a welcoming porch. Lush greenery surrounds the property, while a wooden well adds character to the front yard. Stone pathway leads to the entrance, enhancing the inviting atmosphere.
Home in Chesterfield
4.96 out of 5 average rating, 52 reviews

The River House

DrewRating, 5 stars8 months ago
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.
Guest favorite
A cozy living area features a dark gray sofa with decorative cushions, complemented by two wooden armchairs. A timber-framed window offers a view of the outdoors. A coffee table holds a small centerpiece, and vintage skis are mounted on the wall above the seating.
Home in Wilmington
4.88 out of 5 average rating, 106 reviews

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

JamesRating, 5 stars2 weeks ago
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.
Guest favorite
A spacious home is situated on a vast green lawn, surrounded by trees. The structure features multiple levels and a large deck, providing ample outdoor space. A fire pit is located in the yard, inviting cozy gatherings under the open sky.
Home in Dublin
5 out of 5 average rating, 17 reviews

Private Field House - Spacious 4 Bedroom Home

OdetteRating, 5 stars2 months ago
Absolutely pristine and gorgeous home. We were constantly talking about how perfect it was the entire time we were there. Would definitely stay again!
Guest favorite
A cozy living room features a comfortable beige sofa and matching armchairs, accented by decorative pillows. A central coffee table holds a vase, and light filters through the large windows adorned with cheerful curtains. A fireplace is framed by a stylish mirror, enhancing the inviting atmosphere.
Home in Canaan
4.94 out of 5 average rating, 217 reviews

Hudson River Valley/Berkshires

MarianoRating, 5 stars2 months ago
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

Top guest favorite
A bright living area features wooden flooring and a blend of seating options, including a yellow sofa and patterned armchairs. A glass coffee table sits atop a decorative rug, complemented by artwork on the walls and natural light streaming through the window.
Apartment in Northampton
4.97 out of 5 average rating, 351 reviews

Light filled three bedroom apartment DT Florence!

NicoleRating, 5 stars1 week ago
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.
Top guest favorite
An enclosed porch is furnished with a white rocking chair and various seating options adorned with colorful cushions. A woven storage box sits beside a patterned area rug that features large floral designs. Natural light filters through multiple windows, creating a bright atmosphere.
Apartment in Brattleboro
4.9 out of 5 average rating, 361 reviews

Quiet St in Town, gardens, terrace

KristenRating, 5 stars1 week ago
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!
Top guest favorite
A cozy bedroom features a spacious bed with crisp white linens and a decorative throw pillow. Two nightstands with wall-mounted reading lights are positioned beside the bed. Natural light streams through a window adorned with sheer curtains, enhancing the room's bright and airy feel.
Apartment in Keene
4.97 out of 5 average rating, 187 reviews

"Up Top” at Ro & Oak House

NicoleRating, 5 stars3 days ago
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.
Top guest favorite
A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.
Apartment in Charlemont
4.99 out of 5 average rating, 157 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars1 month ago
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!
Top guest favorite
Two white lounge chairs are positioned around a small black fire pit in a grassy area. Lush greenery and trees define the backdrop, while an open space creates a sense of privacy and tranquility.
Apartment in Brattleboro
4.98 out of 5 average rating, 133 reviews

River View apartment

MarionRating, 5 stars4 days ago
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.
Guest favorite
A cozy living room features a brown leather sofa adorned with patterned cushions. A coffee table with decorative items sits in front of the sofa, while a large window allows natural light to illuminate the space. A potted plant and artwork decorate the room, enhancing its charm.
Apartment in Shelburne Falls
4.97 out of 5 average rating, 117 reviews

River View Apt in Shelburne Falls Historic Village

AllieRating, 5 stars3 weeks ago
Thanks Crystal It was a great spot for the weekend and very comfortable!
Superhost
The updated kitchen features modern appliances, including a black microwave and oven. Light-colored cabinetry contrasts with the granite countertops. A coffee maker sits on the counter, and a dining table is visible, providing a space for meals. The floor is covered with wood-like laminate.
Apartment in Holyoke
4.84 out of 5 average rating, 129 reviews

Quiet bright & sunny 2 bedroom apartment w/ porch

SarahRating, 5 stars1 month ago
It was a great experience, very easy to get to.Super clean we enjoyed our stay!!
Top guest favorite
The living area features sloped ceilings with dormer windows, allowing natural light to fill the space. A comfortable seating area includes two gray sofas and a small dining table. A smart TV is mounted on the wall, and a kitchenette is visible in the background.
Apartment in Northampton
4.98 out of 5 average rating, 705 reviews

Tree Top Suite, cozy downtown apartment

ErinRating, 5 stars2 weeks ago
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

Superhost
A modern living area is presented with a cozy sofa and decorative throw pillows. A sleek wall-mounted TV rests above a rustic fireplace, with a stylish media console below. Light wood accents and a geometric patterned rug contribute to the inviting decor centered around comfort and relaxation.
Condo in Killington
4.94 out of 5 average rating, 171 reviews

Renovated unit, prime location! Shuttle on/Ski off

KristenRating, 5 stars1 month ago
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!
Guest favorite
A snowy landscape showcases the mountain in the background with ski trails visible. The foreground features a winter scene with snow-covered ground and trees. A building is partially visible on the left, adding to the serene atmosphere.
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars2 months ago
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.
Guest favorite
A living area is presented with a spacious purple sectional sofa and an accent chair, creating a comfortable seating arrangement. A wooden coffee table occupies the central space, and large windows allow natural light to fill the room, revealing a snow-covered landscape outside.
Condo in Grantham
4.97 out of 5 average rating, 116 reviews

Cozy Light-filled Condo in Charming Eastman

KatieRating, 5 stars2 weeks ago
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!!
Guest favorite
A spacious living area features a large stone fireplace with a flat-screen television mounted above. Comfortable seating is arranged around a wooden coffee table, creating an inviting space. In the background, the kitchen and dining area are visible, offering a seamless connection to the living space.
Condo in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

PatriciaRating, 5 stars1 month ago
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!
Top guest favorite
A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars1 month ago
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.
Guest favorite
The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.
Condo in Killington
4.9 out of 5 average rating, 129 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

DillonRating, 5 stars2 weeks ago
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!
Superhost
A spacious sleeping area features a large bed with a textured gray coverlet, complemented by two decorative pillows. Flanking the bed are wooden nightstands with lamps. A wall art piece consisting of circular shapes adds visual interest, while natural light filters in through the nearby window.
Condo in Ludlow
4.84 out of 5 average rating, 130 reviews

Okemo Clock Tower Base Ski-in/Ski-out Condo

StephenRating, 5 stars1 month ago
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.
Superhost
A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.
Condo in Killington
4.78 out of 5 average rating, 307 reviews

Serene Top Floor Condo (resort style amenities)

JonRating, 5 stars1 month ago
A wonderful place situated close to the mountain. The amenities were fantastic as well. The only issue was getting the right pin to access the apartment...however Scott responded within seconds so it was minimally disruptive.

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