
Holiday rentals with outdoor seating in Sheffield
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Top-rated rentals with outdoor seating in Sheffield
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Sheffield
House rentals with outdoor seating
Woodstock Historic Artist Estate - The Pond House
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

Lake House in the Berkshire (Access Dock & Canoe
We enjoyed our stay at the house. Mitchell was very responsive and communication was easy. The house is near butternut and GB. Hopefully we will come back in the summer to enjoy the outdoors.

Unwind in the country, stargaze in hot tub
What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.

Lakefront +pets +skiing +bbq +firepit +games
We had a great time, the location is great, right on the water and the fishing was even better. A very quiet lake and much bigger when you are out on it in the kayaks. I would surely stay here again!

A sunny, quiet chalet beautifully decorated.
Great location with easy access to Great Barrington and other Berkshire destinations. Perfect house for families or larger groups, we had everything we needed with various sleeping arrangements. Nice open kitchen and decks. We would be happy to return.

The Gatehouse at Raspberry Ridge
Lawrence and Ilze are great hosts! They actually just live next to the house and they own a farm. We took our kid to visit their farms with lots of beautiful chickens and roosters. My son even has a chance to feed the chickens. We will definitely come back!

Rustic Swedish Barn/Featured in Airbnb Magazine
We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!

Modern Farm House 5 minutes from Great Barrington
We can't say enough good things about Elle's lovely renovated farmhouse! It's a charming, spotless home, and was the perfect size for the four of us. The furniture was comfortable, the kitchen had wonderful appliances and all the cookware we could possibly need, modern bathrooms with plenty of towels and so on! And what a great location—it’s on a lovely road that’s about a ten minute drive to Great Barrington. We had a few questions for Elle and she responded very quickly. We’ve been to the Berkshires many times and this is without a doubt one of our favorite homes. We ook forward to staying here again!
Apartment rentals with outdoor seating

Walk Everywhere! | Relax in Easy Elegance!
Fantastisch!! Charming, comfortable, quite and close in. Love this old house with beautiful woodwork, kousa dogwoods in full bloom in the yard. Great stocked kitchen, although we ate out at the many yummy cafes and restaurants. Mooncloud was a favorite! Comfy, spacious living room. Nice large dining table. Trice was a wonderful host, quick to respond and let us enjoy our space! I am so glad I took a chance on airbnb again - this was one of my favorite stays on airbnb and my favorite in Great Barrington! Would definitely book again!

Relaxing Spa Retreat~Gorgeous View~Walk to Village
Ami’s place was great! Stayed for my birthday and was surprised with a delicious tres leche cake upon my arrival! The view was incredible, amenities were amazing, overall it was everything I hoped for and more. Thanks Ami!

Quiet getaway in the Berkshires
Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy

Bennett Abode
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!

The Beer Diviner Brewery Apartment
Cute room above the brewery was a nice get away for my wife, our little dog, and I. John was friendly and so were all of the other employees and guests. The Irish band was great and the patio by the brewery was very cozy the beers were also delicious too. The room itself was spacious and well furnished with a good size bed and additional day bed. Fun weekend get away for all ages.

Mountain View Retreat~Sunny Hill Golf / Skiing
Definitely a space with great level of thoughts and details makes you feel comfortable and relaxed. Surrounded by the nature, you can immerse yourself in the beautiful mountain view and bird chirps, very peaceful and tranquil. We saw deers walking by, rabbit hiding in bush from raining, and a little chipmunk busy around the house all the time. Thanks Katey for sharing her beautiful home and being a great host, super responsive and provides lots of useful information. We had an amazing time!

Cozy Apartment with Sauna in Historic Stone Ridge
Very convenient location close by to everything we needed! We did have an issue with something in our unit, but Aaron communicated very quickly and was able to let us use the other available unit for the night. Both Air bnbs at the property were very well stocked and spotless. Felt very much at home here!

Hudson River Beach House
Love Janet, love her property, love the atmosphere……….PERFECT in every way! Any need……Janet was doll! Will be back!
Apartment 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!

Trailside At Hunter-Phase II-Hunter NY
This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

Spacious 3 bedroom apt in Lenox historic downtown
Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

Perfect Catskills hiking getaway with fireplace
5 stars, 5 stars, 5 stars!! I would just like to say I’ve stayed in many Air B&Bs before, and this one is by far one of my favorites. The hosts are absolutely amazing. They are proactive in responding and really want you be be comfortable and making sure you have no issues. The price was 100% worth it. I love that they included board games as a part of the space, such a nice touch. The bathrooms and bedrooms were also so clean, and we enjoyed our stay. You can really tell the hosts put a lot of love and care into this place. I can’t say enough good things about them!

Hike, bike & snooze: your summer adventure!
Robert's place was a delight! Spotless with many thoughtful touches. We went for a spring snowboard trip to Hunter and didn't try to walk to the lifts (due to the conditions), but the drive was only a few minutes and super convenient. Robert was very responsive and friendly, and made sure we had everything we needed. The property is great with a lovely deck and well equipped. Highly recommend this property; we hope to be back!

Brand New Outdoor Hot Tub - Luxury 2 Bedroom Suite
Just a short stay but all was seamless. Beds comfy, bathrooms clean and updated. I would stay again.

1 BR Beauty on Hunter Mtn. Ski/Hike from backyard!
Have stayed at many AirBnB's at Hunter mountain over the past few years and Nicole's place was the best by far. Clean and cozy, and you can walk to the lifts. Looked exactly as pictured and was very clean and organized on arrival. Nicole was a great and responsive host.

MountainViewBrightCondo10MinToColgateLakePool
Wonderful stay!! Very clean and cozy space. The host was easy and lovely to communicate with!
Quick stats about holiday rentals with outdoor seating in Sheffield
Total rentals
50 properties
Nightly prices starting at
₹7,789 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
- Six Flags New England
- TPC River Highlands
- Thunder Ridge Ski Area
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Dinosaur State Park
- Beartown State Forest
- Mohawk Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation