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Vacation rentals with outdoor seating in Windham

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Windham outdoor seating rentals

House rentals with outdoor seating

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, 121 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.
Guest favorite
A covered patio area features a seating arrangement with a gray sectional sofa, a blue chair, and a coffee table. Wooden steps lead from the patio to the grassy yard, while sunlight filters through the open space, creating a bright and inviting atmosphere.
Home in Adams
4.92 out of 5 average rating, 12 reviews

Adams Charm

SamanthaRating, 5 stars2 months ago
We loved our stay at Jason’s home. The house was beautifully decorated, clean, and very comfortable. Jason was super responsive whenever we needed anything and he was a tremendous help when our car got stuck in the snow. He spent over an hour of his time trying to help us get our car into a safe place until the storm ended. We would love to stay here again, highly recommend!
Guest favorite
A wooden deck extends towards the water, surrounded by tall trees with bare branches. A dark grill is covered on one side of the deck, and a simple outdoor table with one chair is situated nearby. The water reflects the natural scenery.
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.
Superhost
A bright living room is furnished with a pink sofa and two accent chairs, creating a cozy seating area. A wooden coffee table is centered in the room, while warm light is provided by wall sconces. A textured wall hanging adds visual interest.
Home in North Adams
4.89 out of 5 average rating, 109 reviews

Central Haus (Group getaway on a quiet street)

MichelleRating, 5 stars1 week ago
Great stay at Mian and Anthony's place. Kitchen was well stocked with everything we needed, there was tons of space, and comfy beds. We are grateful that they allowed us an early check in too. Would stay with them again gladly!
Top guest favorite
A spacious living room features a vaulted ceiling and an arched window that allows natural light to flood the space. Comfortable seating arrangements include two red sofas and a patterned area rug. Shelving units display decorative items, while a media system is positioned above the fireplace.
Home in West Brattleboro
4.93 out of 5 average rating, 117 reviews

Modern Spacious Home with Mountain Views

JoannaRating, 5 stars1 month ago
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! ❤️
Guest favorite
Home in Wilmington
4.88 out of 5 average rating, 105 reviews

MtSnow * HotTub * Pool * Air Hockey * 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 private balcony features two outdoor chairs accompanied by a glass table. Lush green trees provide a natural backdrop, while a glimpse of the serene lake can be seen beyond the property, enhancing the tranquil atmosphere of this lakeside retreat.
Home in Enfield
4.95 out of 5 average rating, 102 reviews

Quiet lakeside retreat with private dock.

Mei LeneRating, 5 stars2 weeks ago
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 .
Top guest favorite
A rustic chair and a small table made from a tree stump are positioned by a gentle stream. A glass of rosé wine sits on the stump, with a bottle nearby, surrounded by lush greenery and colorful foliage in the background.
Home in North Adams
4.97 out of 5 average rating, 161 reviews

Bernie's & Betty's

JordanRating, 5 stars1 month ago
We stayed for a few days and the place worked out great! The kitchen is stocked with everything you’d need to include various paper products. Plenty of towels and linens for our family of 6. The entire home was very clean and well maintained. Great communication with Mike, and he even checked in on us to make sure we got settled without issue. We will definitely be staying here again when we travel back to North Adams!

Apartment rentals with outdoor seating

Top guest favorite
A welcoming storefront features a wooden sign for Simon Pearce, accompanied by colorful pumpkins and vibrant yellow mums. The gray building showcases a green roof and large windows, with outdoor seating available on the patio. A blue sky with scattered clouds serves as the backdrop.
Apartment in Chester
4.93 out of 5 average rating, 144 reviews

Lovely 2 Bedroom Apartment w/deck & pond view

AngelaRating, 5 stars2 months ago
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!
Top guest favorite
An open concept living area is highlighted by a comfortable light-colored sofa with decorative pillows. A dark wood coffee table centers the space, while a well-equipped kitchen features modern appliances and a light-colored island with seating. Natural light filters through the window, enhancing the inviting atmosphere.
Apartment in Brattleboro
4.9 out of 5 average rating, 361 reviews

Quiet St in Town, gardens, terrace

KristenRating, 5 stars5 days 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!
Guest favorite
A serene view from the deck showcases a green meadow leading to a small pond surrounded by grass. Rolling hills can be seen in the distance, framed by trees. A few outdoor chairs are placed near the pond, inviting relaxation in the natural setting.
Apartment in Guilford
4.88 out of 5 average rating, 406 reviews

Apartment with a view

C. GavinRating, 5 stars3 weeks ago
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.
Top guest favorite
A private balcony features a small white table and two matching chairs. A decorative orange vase sits atop the table. Surrounding vegetation includes lush green leaves and a prominent white birch tree, providing a serene view of the tranquil woods beyond.
Apartment in Wilmington
4.91 out of 5 average rating, 134 reviews

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars1 month ago
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.
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, 132 reviews

River View apartment

AnnaRating, 5 stars1 month ago
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.
Top guest favorite
A private deck is featured, surrounded by greenery and trees. A glass-top table is set with four metal-framed chairs and a yellow umbrella for shade. Potted flowers add color to the space, inviting relaxation in the outdoors.
Apartment in Dublin
4.97 out of 5 average rating, 227 reviews

Private Dublin apartment nestled in the woods

JenRating, 5 stars4 days ago
This place was so quiet and beautiful. I loved everything about this Airbnb. Linda was extremely helpful. I would love to stay here again.
Guest favorite
A private back deck is showcased, featuring a round glass table surrounded by four black metal chairs. The deck offers views of the river below and the lush hills in the background, enhancing the outdoor space with a serene natural setting.
Apartment in Shelburne Falls
4.97 out of 5 average rating, 117 reviews

River View Apt in Shelburne Falls Historic Village

AllieRating, 5 stars2 weeks ago
Thanks Crystal It was a great spot for the weekend and very comfortable!
Guest favorite
A bright living area showcases a comfortable grey sectional sofa, paired with two small tables and a dining table set for four. Exposed wooden beams and skylights enhance the space, while a soft area rug adds warmth beneath a harmonious arrangement.
Apartment in Williamstown
4.94 out of 5 average rating, 300 reviews

COLD SPRING

KarenRating, 5 stars1 week ago
This was our second stay and we just booked a third. This is the perfect location to visit our college student at Williams for concerts and events. The house is clean and comfortable and the hosts are perfect in every way.

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, 115 reviews

Cozy Light-filled Condo in Charming Eastman

KatieRating, 5 stars1 week 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 ski resort property is depicted, featuring multiple gray wooden buildings with distinct gabled roofs. Balconies are visible on some units, and a gentle slope is seen in the background, hinting at the nearby mountain scenery. Clear skies suggest a bright, sunny day.
Condo in Killington
4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

ZacharyRating, 5 stars2 months ago
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 Windham

  • Total rentals

    30 properties

  • Nightly prices starting at

    $100 before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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