House vacation rentals in Sheffield

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Popular amenities for Sheffield house rentals

House rentals with a pool

Top guest favorite
An outdoor deck surrounds a circular swimming pool, complemented by a patio table and chairs. Several lounge chairs are arranged near the pool, and a large umbrella offers shade. Lush greenery borders the space, creating a private and serene environment.
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 favorite
A spacious two-story house is adorned with winter decorations, featuring dark siding and white trim. Snow coats the ground and branches, adding a serene touch. The entrance is highlighted by a front porch with white railings, surrounded by large windows fitted with seasonal wreaths.
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 favorite
A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.
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.
Guest favorite
A private mid-century country home is seen nestled at the edge of a grassy clearing, surrounded by lush trees. The home features a simple design with a light-colored exterior, under a partly cloudy sky, creating a serene and tranquil setting.
Home in Hudson
4.95 out of 5 average rating, 152 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

JuliaRating, 5 stars2 weeks ago
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!
Superhost
A central living space features a spiral staircase and high cathedral ceilings supported by wooden beams. Light streams through large windows, illuminating a mix of white sofas and chairs positioned on a natural fiber rug. The open layout connects to the kitchen area in the background.
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 favorite
A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.
Home in Ghent
4.88 out of 5 average rating, 314 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

GaryRating, 5 stars2 days ago
Great place. As described. Met our expectations.
Superhost
A cozy living area features a sectional sofa and a coffee table on a soft area rug. Large windows allow natural light to fill the space, while wooden beams accentuate the ceiling. A staircase leads to an upper level, and a comfortable armchair sits beside the fireplace.
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 favorite
An outdoor patio area is showcased, featuring a sparkling pool surrounded by a faux stone deck. Comfortable wooden lounge chairs and a coffee table are positioned near the pool, with a hot tub visible in the background. Lush green hills stretch into the distance under a clear blue sky.
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 favorite
A spacious home is set on a lush green lawn, with a welcoming porch and multiple gabled roofs. The exterior is painted in neutral tones, and a garage is visible on the left. Large windows allow natural light to illuminate the interior.
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 favorite
A spacious living area is highlighted by two large artworks: a framed image of a person holding oranges and a striking mural featuring two figures near a vintage train. The warm wooden floors add a sense of openness to the room.
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!
Guest favorite
A spacious living area features a plush teal sofa and a cozy gray couch. A circular glass coffee table sits on a vibrant area rug. Natural light filters in through large windows, while unique artwork and modern decor enhance the inviting ambiance. A staircase leads to the upper level.
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
A two-story post-and-beam house is set in a lush, green landscape under a clear blue sky. The rustic exterior frames a welcoming front door, while a grassy lawn surrounds the structure, providing a sense of privacy and tranquility.
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 favorite
A blue-brick exterior is complemented by a landscaped yard featuring two lounge chairs with light blue cushions. A dining area with an umbrella sits adjacent to the building, while stone pathways lead to the entrance flanked by greenery.
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
Top guest favorite
A combined living and reading area features wooden beams above and a plush armchair. A decorative arrangement of branches is placed on a side table, accompanied by a cozy throw on the chair. Built-in shelving displays books and decor, with natural light illuminated through the nearby window.
Home in Hudson
4.95 out of 5 average rating, 372 reviews

Rushing Rapids Cottage – a birdwatcher's paradise

KelleyRating, 5 stars2 weeks ago
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.
Superhost
The exterior of a two-story duplex features a blue façade and large windows. A welcoming entrance is highlighted by a wooden front door. Potted plants and vibrant flowers add color to the porch area, enhancing the inviting appearance of the home.
Home in Hudson
4.91 out of 5 average rating, 117 reviews

Hudson BoHo

JoannaRating, 5 stars4 months ago
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!
Guest favorite
An open-concept kitchen and dining area is presented, featuring a large island with eight wooden stools and sleek white cabinetry. A dining table with black chairs is set against a backdrop of large windows that allow natural light to illuminate the space.
Home in Lee
5 out of 5 average rating, 106 reviews

Modern and spacious Berkshires 5bdr retreat.

TheresaRating, 5 stars3 months ago
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

Top guest favorite
The exterior of the home is presented, showcasing a modern two-story structure. Lush landscaping features vibrant azaleas in purple and pink, with well-maintained shrubs bordering a gravel driveway. A garage is attached to the house, complemented by a serene backdrop of greenery.
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 Saugerties
5 out of 5 average rating, 12 reviews

The House on the Hill

NicolasRating, 5 stars9 months ago
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!
Superhost
Home in Nassau
5 out of 5 average rating, 3 reviews

Secluded Lux Mansion Pool Home with Amazing Views

DaifengRating, 5 stars4 months ago
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!
Guest favorite
A light-filled living area features a sofa adorned with green and textured throw pillows. Two stylish chairs complement a round coffee table, and a large bookshelf showcases a collection of books and decorative items. A vibrant area rug covers the wooden floor.
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 favorite
A rustic red wooden cabin is set against a backdrop of lush green trees. The structure features a sloped roof and a welcoming front porch with steps leading up to it. The surrounding area includes gravel pathways and picnic tables for outdoor gatherings.
Home in Colebrook
4.96 out of 5 average rating, 74 reviews

Log Cabin sleeps 30 bunk style on 350 acres

RomaricRating, 5 stars7 months ago
Beautiful time, we can't wait to come again.
Superhost
A charming two-story wooden house is surrounded by lush greenery and colorful flower beds. The exterior features large windows, a balcony on the upper level, and a screened-in porch attached, providing a welcoming entrance set on a quiet country road.
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!
Top guest favorite
A three-story cottage is surrounded by greenery, showcasing a welcoming front porch with railings. The exterior features light blue siding with white trim and a gabled roof. Multiple windows allow natural light to enter, while the manicured lawn adds to the overall charm of the setting.
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 favorite
A private house is framed by a white picket fence, with a gravel driveway leading to an entrance. Surrounding greenery and colorful trees hint at a natural, serene environment. The structure features a mix of siding and a chimney, suggesting a cozy, country aesthetic.
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

    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