
House vacation rentals in Sheffield
Find and book unique houses on Airbnb
Top-rated house rentals in Sheffield
Guests agree: these houses 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 house rentals
House rentals with a pool

Spacious Staycation near HITS & the Hudson
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!

Upstate Family-Friendly House w/ Pool Pets Allowed
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.

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

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Our stay with Christopher was amazing! The house was so beautiful inside and was everything our group needed. The hot tub and backyard space was beautiful as well. One thing to note is that there was no washer/dryer to wash the towels in between hot tub & shower use, so bring extra!

The Round House w/ Heated Pool
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.

Modern Barn on 12 acres w Sauna, FirePit+swimming
Great place. As described. Met our expectations.

Woodland Country Retreat-Pool+FirePit-nearWineries
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.

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

Stockbridge Cape Near Tanglewood!
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.

Hudson New York Grey Victorian
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!

The Martin House, Catskills
A lovely place, with clear and reasonable guidelines, fit to purpose. Would absolutely return.

Secluded Post-And-Beam Retreat
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.

Litchfield County Getaway
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

Rushing Rapids Cottage – a birdwatcher's paradise
We loved staying at Jeffrey and Juan’s quiet home on the rushing Chittenden Creek! Jeff is a communicative, friendly, and accommodating host and would absolutely recommend his place to others. I surprised myself at how much I loved the bird watching (don’t worry, Jeff has binoculars and a book to guide you!). Don’t miss out on the Empire trail for early evening walks! My husband and I stayed at their home for two weeks as we both work remotely and there was plenty of space to spread out and take calls. The plant room in their home is so beautiful that people complimented my ‘digital’ background on zoom! Would absolutely stay again.

Hudson BoHo
Our group of 3 felt right at home! Nice decorator touches - Dash and Albert linens and rugs & lovely soaps added a luxurious feel. We were too busy exploring Hudson to miss the TV, but if that’s important to you, take note. Hosts were super responsive. We can’t wait to return!

Modern and spacious Berkshires 5bdr retreat.
Wonderful accommodations—homey and beautifully furnished. We especially enjoyed the well stocked kitchen as our family loves to cook! Very responsive hosts. They even had a Christmas tree for our young grandchildren! Great for all ages!
Private house rentals

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.

The House on the Hill
Gorgeous house in the heart of Saugerties. The house is located on a quiet street among nature and right next to the water. It is full of old world charm and extremely spacious with a fantastic garden and a very large pool. We were two families (9 total) so we put the whole house to great use. The 5 bedrooms allowed everyone to have their own space. Multiple living rooms and a nice porch were great features The kitchen is well stocked and was put to good use! Claudia and Paul were super reactive to any questions or query. Saugerties is very close (5 min drive) and Woodstock is only a 15 min drive away. Highly recommend for families or group getaway!

Secluded Lux Mansion Pool Home with Amazing Views
Our stay at Barry and Alisha’s place was absolutely amazing! The house is spacious, beautiful, and full of character, with thoughtful details that made it truly special—especially the room with the hidden entry, which was such a fun touch. The property itself is incredible, with the biggest lot we’ve ever seen and private trails that are perfect for relaxing walks. It’s a serene escape from the hustle and bustle of city life, and we left feeling refreshed and recharged. Barry and Alisha were wonderful hosts, and their attention to detail made our stay even better. We had an unforgettable time and would highly recommend staying here to anyone looking for a peaceful retreat. Can’t wait to come back!

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
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.

Log Cabin sleeps 30 bunk style on 350 acres
Beautiful time, we can't wait to come again.

Peaceful Berkshire Getaway (A/C, Lake Access)
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!

Best of Both Worlds! Nature in the Village!
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!

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.
Quick stats about house rentals in Sheffield
Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ331 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
- Hudson Valley Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- The Hamptons Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Boston Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Cape Cod Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Kid-friendly rentals Sheffield
- Family-friendly rentals Sheffield
- Pet-friendly rentals Sheffield
- Rentals with a patio Sheffield
- Rentals with outdoor seating Sheffield
- Rentals with a washer and dryer Sheffield
- Rentals with a fireplace Sheffield
- Rentals with a fire pit Sheffield
- House rentals Berkshire County
- House rentals Massachusetts
- House rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- TPC River Highlands
- Taconic State Park
- Thunder Ridge Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Norman Rockwell Museum
- Opus 40
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mount Southington Ski Area
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Otis Ridge
- Beartown State Forest