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

Adams Charm
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!

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!

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.

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.

The Bumble Bear Inn, Bolton Ldg
This is our second annual visit to the Bumble Bear Inn. We love all the TVs and WiFi but especially the game room! Kitchen is well-stocked and morning coffee in the sunroom is very relaxing. Great place to visit in the winter! Kim and Cameron are very responsive and great!

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!
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
We loved Jaki's apartment. It was very clean, neat, beautifully appointed, and convenient. Jaki welcomed us when we arrived and made herself available. She was friendly, warm, and very responsive. I'm returning to the area for business in the future and will book the same apartment again.

"Up Top” at Ro & Oak House
Had a great time at Hannah’s place. Excellent location, beautiful space, comfortable beds. No complaints!

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
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.

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

Sunny Troy Private Deck Parking Wi-Fi Top Floor
This is a great place, and I experienced very helpful communication and a restful stay. Would consider this location and Susan’s others in the future!
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
Very clean and great location. It was about an 8 minute walk to the Ramshead lodge and we ate at two restaurants within a 5 minute walk. The shuttle was also easy and ran frequently. Would recommend!

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.

Serene Top Floor Condo (resort style amenities)
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.
Quick stats about vacation rentals with outdoor seating in Londonderry
Total rentals
90 properties
Nightly prices starting at
$125 CAD before taxes and fees
Total number of reviews
7.1K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Berkshire East Mountain Resort
- West Mountain Ski Resort
- Monadnock State Park
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Mount Sunapee Resort
- National Museum of Racing and Hall of Fame
- Gooney Golf
- Lake George Expedition Park
- Stump Sprouts Ski Touring Center
- Clarksburg State Park
- Mount Greylock Ski Club
- Bromley Mountain Ski Resort
- Willard Mountain
- Dorset Field Club
- Ekwanok Country Club
- Hildene, The Lincoln Family Home
- Pineridge Cross Country Ski Area
- Northern Cross Vineyard