
Vacation rentals with outdoor seating in Sheffield
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Sheffield
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Sheffield outdoor seating rentals
House rentals with outdoor seating

The Berkshires Mountain Terrace LUX Home Sleeps 7
This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.

Mountain retreat, Catskill
Great spot & perfect for our family. Comfy beds, large and bright modern kitchen, plenty of space in the family room for everyone! There was everything you needed in the kitchen to cook with and we even had baking pans to make brownies! The host sent a welcome email with a list of local attractions & suggestions which was helpful. Close to Wyndham. We loved it! Will stay again!! Thanks!

Airy 5Br-2Ba,Kids Rm, 6TVs,Pvt Fence-yard&Parking!
Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.

Serene Country home 24 mi Mohawk ski area
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries

The Gatehouse at Raspberry Ridge
If your looking for a great quiet stay while visiting Hudson or other local places this home is it. Very clean, super dog friendly. Close to the highways and hidden enough to really be apart of nature.

Mountain house + studio
My friends and I had a lovely stay in Sarah’s home to bring in the new year together. Sarah was very kind, attentive and responsive! Check in was seamless and the home was just as pictured. A great well equipped & cozy space overall. great location as well and would def recommend to others. thank you sarah!

Spacious Mtn House | Ski, Hike, Eat, Shop | Hunter
Rachel's house is ideally located off the main road in Tannersville, close to downtown and 10 minutes from Hunter mountain. It's spacious, squeaky clean, modern, perfect for a group. We were two families with kids ages 4 to 11 and appreciated the 3 beds, 3 baths, washer/dryer and open communal room layout. Rachel was very responsive and check out instructions easy to follow.

Catskill Village House close to dining shops
It was 5 stars from check in to check out!! It is very clean, comfortable, quiet, well outfitted, and in a good location. Plus you can sit on the balcony in the morning sunshine with your coffee. A late evening glass of wine in the dome during a light rain was truly lovely.
Apartment rentals with outdoor seating

Saugerties Village home with great backyard!
The unit had 2 bedrooms and was clean and uncluttered and worked well for our family of 3 adults and 2 young dogs. Though we didn’t use it there was a nice fenced in patio out back. The kitchen was nicely appointed. All in all the unit met our needs and expectations for a last minute short stay. Our host, John, was responsive with any questions we had. We would stay here again.

Apartment on Main St.
As usual, I so much enjoyed my stay. Molly was hard at work in her beautiful flower garden, which are lovely to see first thing in the morning. I'll be back, for sure.

Homey Haven:Inviting Airbnb Suite with kitchen
Nichole’s place was a great stay in New Paltz. The location was perfect and she was super responsive when needed!

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!

Charming apartment with breathtaking view!
Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.

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

2BR|2 Queen Beds|Balcony|Parking|Strong Wifi
This is the best Airbnb I have stayed in Poughkeepsie and overall in New York State. The place is very clean , it was recently refurbished , has good equipment for cooking, it is spacious. The parking is easy and convenient. Check in was smooth. Owners are responsive. Very strongly recommend it.

Tuscan Garden Apt at Café Capriccio Albany, NY
Great stay at Marlene's place! Good location, nice apartment. Everything as described. Responsive host. Would recommend!
Condo rentals with outdoor seating

Pacer's Pasture
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

Spacious 3 bedroom apt in Lenox historic downtown
Beautiful apartment with lots of rooms-comfy sitting areas and lots of light. It was very nicely appointed and the checkin was simple. We will definitely be back as the location is ideal.

Hunter & Windham: Hikes, Lakes, 2BR
My friends and I really enjoyed our stay. We hiked the devils path trail and Dimitry’s place was perfectly close to the trail and the restaurants around it. His place was great to go back to with a great shower and bath, a beautiful view and very cozy place, with coffee and a coffee maker. Very clean and Dimitry was responsive the whole way through and checkin and out was very easy. Would highly recommend and would stay again.

Flowers & Falls Spot House
Superhost ! Was so accommodating to get us in last minute since our other Airbnb didn’t work out. He was so responsive and helpful with the snow storm as well ! We were so glad to have found this gem and have such a gracious host. The location is perfect and walkable to all the restaurants and markets. Also 15 mins away from Berkshire East ! This was a great find and we are thankful for it !

Wyndham Bentley Brook
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

Cozy Condo @ Jiminy Peak
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

Lovely Modern 2-bedroom condo near Candlewood Lake
The house was very clean and modern. It had everything we needed for a weekend stay. The location is perfect! It's very close to downtown New Milford and restaurants. Would definitely recommend staying here!
Quick stats about vacation rentals with outdoor seating in Sheffield
Total rentals
50 properties
Nightly prices starting at
$125 CAD before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Hunter Mountain
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Six Flags New England
- Albany Center Gallery
- TPC River Highlands
- Berkshire East Mountain Resort
- Taconic State Park
- Thunder Ridge Ski Area
- Walkway Over the Hudson State Historic Park
- Bushnell Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
- Pineridge Cross Country Ski Area
- Naumkeag
- Beartown State Forest