House holiday rentals in Sheffield

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for house rentals in Sheffield

House rentals with a pool

Guest favourite
Home in Saugerties
4.94 out of 5 average rating, 68 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

YuliaRating, 5 stars2 months ago
We stayed as a family of 4, including a 1 year old and 3.5 year old. The place was extremely comfortable and had everything we would need for our stay. The kids enjoyed the playroom and kids room with lot of toys and books. Kitchen was fully stocked with plates, utensils, cooking ware, and a high chair. Place could easily accommodate more people, very clean, comfy beds. Property manager was very responsive. Short drive to downtown area. Lastly, great outdoor area, we’d love to plan a trip there when warmer as well!
Top guest favourite
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars6 months ago
My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!
Guest favourite
Home in Saugerties
4.98 out of 5 average rating, 60 reviews

Upstate Family-Friendly House w/ Pool Pets Allowed

NasimRating, 5 stars3 months ago
We had a great time at Natalia house, a very big house with a lot to do for my three years old daughter. Will definitely stay here again.
Guest favourite
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Superhost
Home in Stanfordville
5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

JonathanRating, 5 stars5 months ago
An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.
Guest favourite
Home in Saugerties
4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars6 months ago
We had a terrific stay. The house was exactly as advertised.
Superhost
Home in Litchfield
4.9 out of 5 average rating, 49 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

Sarah & SteveRating, 5 stars6 months ago
Jean was extremely friendly to let us book a last-minute stay at this home the day prior. The home is in a good location and has a nice layout, although we were only three people and did not use all of the house. One thing to note is that the heat was restricted to 70° and 72° depending on the thermostat and my elderly parents from Florida were extremely cold the entire weekend, wearing jackets and warm hats the round the clock even inside during their visit. Sadly for our group, the foliage of Fall had all disappeared save for one tree. Also, the pool was not available so we cannot comment on this. All in all, a lovely home, but definitely priced quite high, considering.
Guest favourite
Home in Catskill
4.9 out of 5 average rating, 104 reviews

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

JyothiRating, 5 stars1 month ago
We had such a peaceful and beautiful stay here. We came with our young kids and it was perfect. The home is incredibly warm, thoughtfully decorated, and fully furnished, a lot of care and intention went into every detail. Beyond what others have shared, we appreciated the sound system in the dining and living room (perfect for cooking vibes), the nightlights for the kids, a fully stocked kitchen, —plenty of towels, wine stoppers, even a cocktail kit!. Our kids were obsessed with the play area—they spent hours outside every day! They also have an arcade shed! Since we visited in the winter, we didn’t get to use the pool, hot tub was a hit. The house is in a peaceful, private area with a view of the mountains, and in the mornings we saw deer in the fields. The natural light that pours into the home was one of my favorite parts—it made everything feel calm. It’s a beautiful home-The hosts were also incredibly responsive and kind. We can’t wait to visit again.

Weekly house rentals

Top guest favourite
Home in Stockbridge
4.93 out of 5 average rating, 41 reviews

Stockbridge Cape Near Tanglewood!

MarkRating, 5 stars4 months ago
Very nice accommodations in a great location. A vehicle needed to get around to plentiful hiking, shops in nearby towns, and cultural sites. Very nice home for family gatherings and with all necessary amenities.
Guest favourite
Home in Rosendale
4.91 out of 5 average rating, 47 reviews

Rosendale vacation

DanielleRating, 5 stars6 months ago
My friends and I stayed here for our annual Girl's Trip and the house was perfect for our weekend getaway. We loved the open concept and the location was peaceful. We also loved how close it was to New Paltz and Kingston for shopping and our favorite coffee shop - Blackbird Cafe - was only a 7 min drive away. We would definitely stay here again!
Guest favourite
Home in Hudson
4.92 out of 5 average rating, 202 reviews

Hudson New York Grey Victorian

KarlaRating, 5 stars2 months ago
This house was perfect for our girls’ weekend in Hudson! It was spacious, clean, and had so much character. The location was great—just a short 5-minute drive to Warren Street. We didn’t walk due to the cold weather but it was definitely close and convenient. Would definitely stay here again!
Superhost
Home in Wallkill
4.86 out of 5 average rating, 121 reviews

Modern Upstate Gem Surrounded by Trees | Hot Tub

RobertoRating, 5 stars1 month ago
I had a wonderful stay at this beautiful modern home in Wallkill, NY. Tucked away on a quiet street with plenty of privacy from the surrounding trees, it felt like the perfect escape from the city. My favorite part was the open-concept kitchen and living area, with expansive windows that made it feel like I was immersed in nature while still enjoying the comfort of being indoors. It was the ideal space to rest, relax, and recharge. If you're looking for a peaceful getaway, I highly recommend this home!
Guest favourite
Home in Catskill
4.98 out of 5 average rating, 406 reviews

The Martin House, Catskills

christopherRating, 5 stars2 weeks ago
A lovely place, with clear and reasonable guidelines, fit to purpose. Would absolutely return.
Superhost
Home in Ulster Park
4.88 out of 5 average rating, 227 reviews

Entire lake house to yourself. Great for groups

Maggie FuentesRating, 5 stars1 week ago
Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!
Superhost
Home in Ancram
4.8 out of 5 average rating, 112 reviews

Secluded Post-And-Beam Retreat

SarahRating, 5 stars2 months ago
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.
Guest favourite
Home in Kingston
4.89 out of 5 average rating, 124 reviews

Cozy Kingston home on 1 acre! Kid & Pet Friendly

JamieRating, 5 stars1 month ago
We felt right at home in this beautiful home and surrounding space. It’s an older home with quirks, but tons of charm! It was very well stocked, with clear labels and instructions. Yanna was extremely responsive with great recommendations. Great location to explore Kingston and nearby surrounding areas. We especially enjoyed the outside space with the front porch and deck perfect for morning coffee while the kids enjoyed the hammock and tent! We had a wonderful stay in this cozy, comfortable home. Thank you!

Private house rentals

Guest favourite
Home in Monterey
4.97 out of 5 average rating, 34 reviews

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

GallianeRating, 5 stars2 months ago
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.
Guest favourite
Home in Hudson
4.94 out of 5 average rating, 18 reviews

The Orchard House-Entire Home

BryanRating, 5 stars2 months ago
We had an amazing stay at Mitch’s property! Mitch was an incredibly supportive and responsive host, making everything seamless from check-in to checkout. The house itself is beautiful—spacious, peaceful, and perfectly located right off the road while still feeling secluded. We were lucky to experience stunning snowy views during our stay, which made it even more special. The amenities were great, making it an ideal getaway with friends. Highly recommend this place for a relaxing retreat!
Top guest favourite
Home in Saugerties
5 out of 5 average rating, 203 reviews

Lilac House- It's for the Birds

BarishRating, 5 stars1 month ago
The Lilac House is the ultimate dream AirBnB! Kathy is the most communicative, proactive, and thoughtful host I've ever encountered. My group felt like we were being personally attended to and had a true bed and breakfast experience, despite Kathy not being physically present. The house is lovely and has everything you could possibly imagine you'd need. We had such a relaxing fantastic weekend, birdwatching from the hot tub. The area is great, with Kingston just a 15 minute drive away, and such a cool town! Rhinebeck is a bit further out but also great. Great food and hikes to be had all over.
Superhost
Home in Canaan
4.96 out of 5 average rating, 72 reviews

Peaceful Berkshire Getaway (A/C, Lake Access)

PaulRating, 5 stars9 months ago
Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!
Guest favourite
Home in Warren
4.94 out of 5 average rating, 108 reviews

Litchfield County Getaway

DemianRating, 5 stars4 months ago
Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend
Guest favourite
Home in Greenville
4.87 out of 5 average rating, 244 reviews

Beautiful Fall cabin, North Catskills/Greenville

MaureenRating, 5 stars3 months ago
When I first pulled up to Kliment's, I literally teared up - that's how breath-taking his spot is. It was just what the doctor ordered... if doctors actually treated your mind, body, and soul and not just your body :) Seriously though, Kliment's place was an oasis for me: private, quiet, peaceful, with amazing views of the Catskill mountains. His home itself was beautifully decorated, simple yet super cozy, and had everything I needed and then some. (And the chickens were lovely company as well!) Kliment is one of the best Airbnb hosts I have ever had, hands down. With a very hectic schedule, Kliment was flexible, responsive, kind and patient with accommodating my many change requests and needs throughout my stay. Kliment is not just a wonderful host, but also a truly wonderful person - the world needs more people like him. In short: I can't recommend Kliment's home or him as a host enough! If you are hovering over the "Reserve Now" button, book it!!! You won't regret it! :)
Top guest favourite
Home in Catskill
4.95 out of 5 average rating, 154 reviews

Best of Both Worlds! Nature in the Village!

JeaniaRating, 5 stars4 months ago
We had an absolutely wonderful stay at this Airbnb! From the moment we arrived, the host was incredibly welcoming and made sure we had everything we needed for a comfortable stay. The space was clean, cozy, and beautifully decorated, with thoughtful touches throughout. The location was perfect—quiet yet conveniently located. I would highly recommend this place for anyone looking for a relaxing and enjoyable getaway!
Guest favourite
Home in Craryville
4.92 out of 5 average rating, 113 reviews

The Gatehouse at Raspberry Ridge

JenniferRating, 5 stars1 week 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.

Quick stats about house rentals in Sheffield

  • Total rentals

    50 properties

  • Nightly prices starting at

    £67 before taxes and fees

  • Total number of reviews

    2.1K 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

Destinations to explore