Vacation rentals with outdoor seating in Wilmington

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Popular amenities for Wilmington outdoor seating rentals

House rentals with outdoor seating

Top guest favorite
A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.
Home in Bennington
4.99 out of 5 average rating, 292 reviews

Cozy Modern Sugar House with spectacular views.

SamanthaRating, 5 stars1 week ago
5 stars all around! The view and the setting are magical. The house is brilliantly appointed and designed. What a dream to stay in this house!! We want to come back for a stay in every season to experience it again and again! The interior is extremely cozy while being beautiful at the same time. One of the best Airbnb homes we've ever stayed in! Book your stay now -- you will love it!!
Top guest favorite
Adirondack chairs and a small side table are positioned on a spacious deck, offering an unobstructed view of Okemo resort. The winter landscape features snow-covered ground, complemented by a clear blue sky and distant mountain views.
Home in Ludlow
5 out of 5 average rating, 111 reviews

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home

AmyRating, 5 stars1 day ago
I can only say wonderful things about this property! Everything was beautiful both inside and out. The house was very clean and organized and was also extremely well stocked. Anything that we needed we found in this house. And everyone in our group said the beds were very comfortable… which is very important to me! Erik was great with communication and very proactive. He sent us a note about a week before we checked in that had everything we needed to know; it was quite helpful. I highly recommend this home….and as an added bonus, the view is spectacular! You will not be disappointed if you stay here!
Guest favorite
An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.
Home in Londonderry
4.99 out of 5 average rating, 135 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

GeorgiaRating, 5 stars1 day ago
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!
Guest favorite
Home in Bennington
4.98 out of 5 average rating, 136 reviews

The Gate House--Experience Vermont!

ElizabethRating, 5 starstoday
What an amazing place! We were struck by its charm the moment we arrived. Everything was so well appointed and beautiful. We just wish we could have stayed longer and explored Bennington more! We came for a Williams College graduation and so the weekend was busy but we had some wonderful meals together at the house and also a little time to explore the countryside around. We hope to come back to this magical place sometime soon!😊
Superhost
A sprawling grassy yard is surrounded by trees, providing natural shade. A wooden deck and seating area are positioned in the background, inviting outdoor relaxation. The white house is visible beyond the tree line, contributing to the serene countryside setting.
Home in Readsboro
4.86 out of 5 average rating, 127 reviews

June in Vermont! (Pet Friendly)

JudahRating, 5 stars6 months ago
This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.
Top guest favorite
A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.
Home in West Windsor
4.98 out of 5 average rating, 124 reviews

Birdie's Nest Guesthouse

KyraRating, 5 stars2 weeks ago
Loved our stay! Everything was cozy and easy; no issues at all. The heated bathroom floor ended up being one of our favorite parts (so nice!), and the whole place just felt super relaxing. Didn’t need to contact the host because everything was smooth from start to finish. Would definitely come back!
Superhost
A single-story house features a light grey exterior with white trim and a welcoming front door. Flanking the door is a stone walkway leading to a grassy yard, where two white adirondack chairs are positioned. A small flowerpot adds a touch of color near the entrance.
Home in Shaftsbury
4.89 out of 5 average rating, 152 reviews

Cheerful 1 bedroom cottage

EstellaRating, 5 stars4 days ago
Glenn was incredibly kind and responsive, and the cottage was exactly like the pictures. The space was perfect for a couple-day getaway before starting my MFA! Also, if you need good local recommendations, Glenn has you covered.
Top guest favorite
A charming two-story, red-paneled house features a welcoming front porch with white railings. Lush greenery and flowers line the stone walkway leading to the entrance, creating an inviting approach to the home.
Home in North Adams
4.98 out of 5 average rating, 422 reviews

Steps to MoCA private house + SAUNA!

DouglasRating, 5 stars3 days ago
This beautiful vintage home is well cared for and spotless. A very pleasant and peaceful place to breath easy and rest after seeing the plentiful local sights.

Apartment rentals with outdoor seating

Guest favorite
An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.
Apartment in Townshend
4.94 out of 5 average rating, 239 reviews

Private Apt. on Farm, Hot Tub with views!

MathildeRating, 5 stars1 week ago
Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!
Top guest favorite
The bright studio features a cozy sleeping area with a spacious bed, a comfortable yellow armchair, and two plush couches. A coffee table sits in the center, with large windows allowing natural light and views of greenery. A television is mounted on the wall.
Apartment in Shelburne Falls
4.97 out of 5 average rating, 559 reviews

In town, newly renovated studio with private deck

JuliaRating, 5 stars1 week ago
stayed here the night before my wedding and carrie was such a great host! she was so accommodating and the space was beautiful. there were so many little touches that made our stay amazing! would stay here again!
Guest favorite
A gently sloping lawn leads up to the light-colored building, framed by lush gardens and vibrant greenery. A pair of purple Adirondack chairs sits invitingly on the grass, offering a serene spot to enjoy the surrounding landscape.
Apartment in Marlboro Township
4.93 out of 5 average rating, 264 reviews

Shakespeare’s Folly Side Farm and AirBnB.

DanRating, 5 stars1 week ago
William is an excellent host and his place is wonderful. I’ve stayed with him. Multiple times. Recommended!
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, 367 reviews

Quiet St in Town, gardens, terrace

LeighRating, 5 stars6 days ago
Jaki's place is super cute and at the back of the building, so nice privacy and quiet as well. The kitchen had all the needed equipment to cook tasty breakfasts, and was well stocked with coffee. Would definitely stay here again on a return trip to Vermont.
Guest favorite
A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.
Apartment in Dummerston
4.96 out of 5 average rating, 225 reviews

HeART Barn Retreat

DaraRating, 5 stars1 month ago
Really exceeded expectations. I grew up in Brattleboro and needed to come for two nights to see my mom. There are no decent hotels in the area and so Brianna’s place was a welcome reprieve from what would have otherwise been a terrible experience. The bed was super comfy and the 4+ pillows on the bed appreciated. It has a whole boho farmhouse chic minimalist vibe and the comfort of the furniture, cleanliness and coziness made it a great short term stay. We will stay again definitely! easy drive to town.
Top guest favorite
A tranquil sleeping area features a wooden bed topped with a vibrant patterned quilt. Natural light enters through a window, illuminating the space. A wooden cabinet and a side table with a lamp add functionality, complemented by artwork on the walls showcasing nature scenes.
Apartment in East Chatham
4.95 out of 5 average rating, 120 reviews

Bennett Abode

AmandaRating, 5 stars1 day ago
We thoroughly enjoyed our stay at the Bennett’s Abode! Larry and Lana’s airbnb had just about everything a visitor would need and they even included a detailed binder full of information and ideas pertaining to the area. Larry was so prompt with his responses and always kept us in the loop. He even provided several great hiking ideas that we utilized throughout our stay at his home. We were so grateful for the overall experience and left with incredible memories!
Top guest favorite
A modern home is situated on a sloped driveway surrounded by trees, with a green lawn and landscaped stone features. Solar panels are visible on the roof. Two vehicles are parked under a covered deck, which extends from the main structure.
Apartment in Brattleboro
4.95 out of 5 average rating, 175 reviews

Contemporary forest eco-retreat, mountain views

AndyRating, 5 stars2 weeks ago
We had a great visit! Millicent and Tony were very welcoming and responsive when we had questions, and the space was great—comfortable and a great view (when the weather cooperated). The recycling/composting rules are involved but they provided extensive explanations that made it easy to do the right thing. It was a chilly weekend but we stayed cozy, and the location was great for exploring Brattleboro and the surrounding area. We'll be back!
Top guest favorite
A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.
Apartment in Petersburgh
4.88 out of 5 average rating, 183 reviews

The Beer Diviner Brewery Apartment

HeidiRating, 5 stars1 week ago
Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!

Condo rentals with outdoor seating

Top guest favorite
The dining area features a large wooden table surrounded by six stools. A metal-framed desk and chair are present nearby, along with a coffee maker and additional kitchen appliances. Light wood flooring complements the neutral walls, creating a spacious and functional environment.
Condo in Ludlow
4.98 out of 5 average rating, 124 reviews

Main St Escape | Explore Downtown Ludlow

RobertoRating, 5 stars3 months ago
Clean, great location, easy check in/out, and friendly host - would definitely stay again.
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 stars3 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 spacious dining area features a long wooden table that seats eight, complemented by modern light fixtures. Large windows allow natural light to fill the room, while a sliding glass door offers access to a private outdoor space. A console cabinet is visible against the wall.
Condo in Dover
5 out of 5 average rating, 15 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

OferRating, 5 stars2 days ago
This place is so welcoming and tasteful. Lots of in-house activities for the evening, when it's raining, or just when you feel like staying in. An easy recommendation.
Top guest favorite
A modern living room corner features a brown leather recliner with high backrest beside a window. A small table holds a potted plant, while a wood stack is positioned against the wall for a rustic touch. Natural light filters through brown curtains.
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars2 months 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.
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 stars2 months 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.
Guest favorite
A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.
Condo in Dover
4.95 out of 5 average rating, 60 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

WifeCherylannRating, 5 stars3 weeks ago
Excellent location and central to all things fun in southern Vermont. Loved the sports center amenities. Very peaceful considering it was end of mud season and not busy at all. We used the pool, workout facilities and locker room. Even had a fireplace we could use ! Christine was incredibly responsive and welcoming. Would recommend to others and would stay again if in the area.
Guest favorite
The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.
Condo in Stratton
4.94 out of 5 average rating, 103 reviews

Great 2 bedroom condo at Stratton Mountain

KatieRating, 5 stars3 months ago
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!!
Guest favorite
A cozy living room showcases two plush couches and a small wooden coffee table. A gas stove is nestled in a brick corner, while sliding doors offer views of the outdoors. Colorful lights frame the window, adding a touch of charm to the space.
Condo in West Dover
4.9 out of 5 average rating, 52 reviews

Ski Condo 5 Min from Mt Snow

JadeRating, 5 stars3 weeks ago
Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!

Quick stats about vacation rentals with outdoor seating in Wilmington

  • Total rentals

    170 properties

  • Nightly prices starting at

    G$16,787 GYD before taxes and fees

  • Total number of reviews

    9.1K reviews

  • Family-friendly rentals

    140 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    50 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Wilmington
  6. Rentals with outdoor seating