House holiday rentals in Sheffield

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Sheffield

House rentals with a pool

Top guest favourite
Home in New Paltz
4.98 out of 5 average rating, 489 reviews

midcentury mod * POOL * walk out trail to mohonk

EleonoraRating, 5 stars3 weeks ago
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍
Guest favourite
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars3 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Superhost
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars3 weeks ago
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!
Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 144 reviews

4Br Mountain Brook House on 130 acres w/ trails

AnnetteRating, 5 stars2 weeks ago
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.
Guest favourite
Home in Woodstock
4.92 out of 5 average rating, 244 reviews

Little owl Japanese teahouse: pool is OPEN

JaneRating, 5 stars2 weeks ago
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.
Top guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 73 reviews

Stunning luxury home with pool

StephanieRating, 5 stars2 weeks ago
Beautiful home! Extremely clean upon arrival and excellent communication. Everything in the house was clearly labeled and directions for check-in and check-out were very clear. Sadly it rained our entire stay so we could not enjoy the pool or the beautiful backyard, but we still had a lovely stay. We hope to come back soon!
Guest favourite
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Superhost
Home in Great Barrington
4.8 out of 5 average rating, 5 reviews

Summer Chalet w/ Pool + Private Hiking Trails

DelmarRating, 5 stars4 months ago
Stayed here with three others for work. The house was clean and well updated. We had no issues and will look to stay here again.

Weekly house rentals

Guest favourite
Home in Copake
4.97 out of 5 average rating, 36 reviews

TREE FARM Hilltop Getaway: Majestic Mountain Views

KatherineRating, 5 stars4 months ago
We had a wonderful, restful stay in this beautiful home. The ambience is so peaceful and the home is spotless, with many thoughtful touches for guests. We'd definitely stay again!
Top guest favourite
Home in Hillsdale
5 out of 5 average rating, 51 reviews

Cambridge Hill Farmhouse - Sauna - Swimming Pond

janetRating, 5 stars5 days ago
This was a perfect vacation home for our family trip. Spacious house with beautiful indoor and outdoor spaces, a well equipped kitchen, luxurious and extremely comfortable furnishings and a location that makes visits to surrounding charming towns so easy.
Top guest favourite
Home in Salisbury
4.99 out of 5 average rating, 68 reviews

Curated Contemporary for lakes, forest & ski hills

QuirineRating, 5 stars2 weeks ago
We were in the area for our son’s graduation. It was the perfect place to stay as a family for a few days. Highly recommend!
Superhost
Home in Great Barrington
4.76 out of 5 average rating, 92 reviews

Cozy Berkshire Getaway

TashaRating, 5 stars1 month ago
We were happy with this AirBNB and would stay here again. It was nice and quiet but a very short drive into Great Barrington. Close to lots of hiking. Updates have been made since some of the previous reviews. There are two couches in the living room and some of the stock items in the kitchen for convenience.
Guest favourite
Home in Hillsdale
4.94 out of 5 average rating, 84 reviews

Sun-drenched cottage surrounded by farmland.

MadiRating, 5 stars3 weeks ago
Our stay here was fantastic! The house was beautiful and had everything you could need to feel right at home. Including a kitchen stocked with essentials, lots of fire wood and games. The location of perfect right between Hudson and Great Barrington and it felt super private. Would definitely stay here again.
Guest favourite
Home in Salisbury
4.93 out of 5 average rating, 15 reviews

Stylish getaway in the Berkshires

NedRating, 5 stars2 weeks ago
Bright, light good layout inside and short walk to Salisbury and very short drive to Lakeville. Would definitely stay here again
Top guest favourite
Home in East Jewett
4.98 out of 5 average rating, 40 reviews

Creekside Couple's Retreat w/Hot tub, Sauna & More

IzabelaRating, 5 stars2 days ago
My husband and I were blown away by the beauty and thought that was put into this private destination. The moment you step on property, the freshness of the air and sounds of the creek are immediately calming. Diana was incredibly nice and very communicative before and during the entire stay. Activities: The sauna, creek, hot tub, pizza oven, grill, fire place/pits, hammocks- the amenities are amazing and unlike any other Airbnb I have ever been in before. So much that besides a quick dinner out one night (12 min away) and a nice walk around the Mountain Top Arboretum with our dog, we wanted to spend our time at the property. We called it our personal sanctuary spa!! The home: The home style is minimalistic but homey and every single item is top notch quality. There are no shortcuts- the entire place is a work of art. The bedroom and bathroom inspired me to reanalyze my own bedroom style. Thank you for upping the Airbnb game!! Can’t wait to come back to this magical spot! ✨
Guest favourite
Home in Salisbury
4.95 out of 5 average rating, 38 reviews

Serene & Modern 3BDRM Farmhouse - EV Charger

GwenRating, 5 stars5 months ago
Stayed with my best friends from Hotchkiss as a little sweet reunion—adorable house, super clean, and fantastic location. The sweet Williams pastries for breakfast were the sweetest touch! Really a wonderful place to stay.

Private house rentals

Guest favourite
Home in Salisbury
4.96 out of 5 average rating, 25 reviews

Peace at Last

GraceRating, 5 stars2 weeks ago
This was my family's second time staying at Jennifer's home, and we will be back again soon! The moment you step you, you feel you're in a serene getaway in a lovely cottage. Our host met every need and went above and beyond on flexibility. This is such a gem in Salisbury!
Guest favourite
Home in Pleasant Valley
5 out of 5 average rating, 27 reviews

The Wildflower House

MatthewRating, 5 stars1 month ago
Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!
Guest favourite
Home in Sheffield
4.83 out of 5 average rating, 12 reviews

Deck, River Views, Mini Gym, Sleeps 8

JosephRating, 5 stars8 months ago
The home was exactly the way it is in the photos, only better! Everything was clean and spotless. Plenty of kitchen and laundry supplies to use. The home is in a very secluded and in a quiet neighborhood. You will never see another person unless you drive out of the very long driveway and into town. The backyard was scenic and perfect for the fall season. Overlooking the river, especially in the fall is very scenic and was perfect for what we were hoping for. Communication with the Rental property was kind, courteous and professional. The even offered us a late check out as long as they did not rent the property that day. Me and my 5 family members were very comfortable and enjoyed our stay. I highly recommend this property for all seasons. Will definitely return.
Guest favourite
Home in Egremont
4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars3 weeks ago
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!
Top guest favourite
Home in Canaan
5 out of 5 average rating, 21 reviews

Fickle Fox Farm. Spring in the air, Summer is soon

BradRating, 5 stars5 months ago
Staying at Amanda and Andrew’s place in Canaan, CT is an exceptional airbnb experience. The home and property are in excellent condition, exactly as pictured in the airbnb profile . And, Amanda and Andrew are quintessential hosts, friendly and responsive. We cannot recommend staying here highly enough. Thank you Amanda & Andrew !
Guest favourite
Home in Port Ewen
4.93 out of 5 average rating, 27 reviews

Hudson Riverfront Mid-Century Modern Home

KevinRating, 5 stars3 weeks ago
A beautiful, comfortable house right on the Hudson with stunning views. We loved watching all the life on the river, herons and loons and ducks, as well as boats from tiny crafts to massive barges. There are great hikes just a short distance away. It is a perfect place to rest, write, draw, and make music.
Top guest favourite
Home in Sharon
5 out of 5 average rating, 28 reviews

Nature lover’s retreat in NWCT, breathtaking views

ScottRating, 5 stars5 months ago
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!
Guest favourite
Home in Litchfield County
4.94 out of 5 average rating, 17 reviews

70’s Retro House

TristanRating, 5 stars4 months ago
Had an awesome stay while visiting family for the week! Daryl made it very easy to choose the place. Everything was very detailed and just as described! The fireplace was very comforting during my chilly stay. Will definitely be booking the place again in the future!

Quick stats about house rentals in Sheffield

  • Total rentals

    50 properties

  • Nightly prices starting at

    ₹7,789 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