Vacation rentals with outdoor seating in Sheffield

Find and book unique accommodations with outdoor seating on Airbnb

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Popular amenities for Sheffield outdoor seating rentals

House rentals with outdoor seating

Top guest favourite
Home in Egremont
4.96 out of 5 average rating, 120 reviews

The Berkshires Mountain Terrace LUX Home Sleeps 7

CourtneyRating, 5 stars2 months ago
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.
Superhost
Home in East Durham
4.6 out of 5 average rating, 5 reviews

Mountain retreat, Catskill

MargueriteRating, 5 stars10 months ago
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!
Guest favourite
Home in Albany
4.81 out of 5 average rating, 52 reviews

Airy 5Br-2Ba,Kids Rm, 6TVs,Pvt Fence-yard&Parking!

BjRating, 5 stars3 months ago
Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.
Guest favourite
Home in New Milford
4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago
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
Top guest favourite
Home in Craryville
4.92 out of 5 average rating, 113 reviews

The Gatehouse at Raspberry Ridge

JenniferRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Elka Park
5 out of 5 average rating, 6 reviews

Mountain house + studio

AntoinetteRating, 5 stars4 months ago
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!
Guest favourite
Home in Tannersville
4.98 out of 5 average rating, 89 reviews

Spacious Mtn House | Ski, Hike, Eat, Shop | Hunter

SarahRating, 5 stars2 months ago
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.
Guest favourite
Home in Catskill
4.94 out of 5 average rating, 110 reviews

Catskill Village House close to dining shops

JulieRating, 5 stars1 week ago
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

Guest favourite
Apartment in Saugerties
4.93 out of 5 average rating, 331 reviews

Saugerties Village home with great backyard!

DoreenRating, 5 stars2 weeks ago
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.
Top guest favourite
Apartment in Torrington
4.98 out of 5 average rating, 163 reviews

Apartment on Main St.

JoanRating, 5 stars1 week ago
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.
Superhost
Apartment in New Paltz
4.87 out of 5 average rating, 291 reviews

Homey Haven:Inviting Airbnb Suite with kitchen

ElizabethRating, 5 stars3 days ago
Nichole’s place was a great stay in New Paltz. The location was perfect and she was super responsive when needed!
Top guest favourite
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!
Guest favourite
Apartment in Burlington
4.85 out of 5 average rating, 108 reviews

Charming apartment with breathtaking view!

RebeccaRating, 5 stars8 months ago
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.
Guest favourite
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!
Guest favourite
Apartment in Poughkeepsie
4.97 out of 5 average rating, 126 reviews

2BR|2 Queen Beds|Balcony|Parking|Strong Wifi

RaulRating, 5 stars4 months ago
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.
Superhost
Apartment in Downtown Albany
4.88 out of 5 average rating, 112 reviews

Tuscan Garden Apt at Café Capriccio Albany, NY

PeterRating, 5 stars4 days ago
Great stay at Marlene's place! Good location, nice apartment. Everything as described. Responsive host. Would recommend!

Condo rentals with outdoor seating

Guest favourite
Condo in Litchfield County
4.95 out of 5 average rating, 21 reviews

Pacer's Pasture

CerayeRating, 5 stars4 months ago
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!
Guest favourite
Condo in Hancock
4.95 out of 5 average rating, 58 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

EladRating, 5 stars2 weeks ago
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.
Guest favourite
Condo in Lenox
4.97 out of 5 average rating, 33 reviews

Spacious 3 bedroom apt in Lenox historic downtown

ThomasRating, 5 stars4 months ago
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.
Guest favourite
Condo in East Jewett
4.97 out of 5 average rating, 29 reviews

Hunter & Windham: Hikes, Lakes, 2BR

LauraRating, 5 stars6 months ago
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.
Superhost
Condo in Shelburne Falls
4.91 out of 5 average rating, 46 reviews

Flowers & Falls Spot House

MelanieRating, 5 stars2 months ago
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 !
Superhost
Condo in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars14 months ago
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!!!
Guest favourite
Condo in Hancock
4.86 out of 5 average rating, 152 reviews

Cozy Condo @ Jiminy Peak

ElizabethRating, 5 stars2 months ago
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.
Condo in New Milford
4.75 out of 5 average rating, 28 reviews

Lovely Modern 2-bedroom condo near Candlewood Lake

VitoRating, 5 stars19 months ago
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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