
Pet-friendly vacation rentals in Sheffield
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Top-rated pet-friendly home rentals in Sheffield
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Vacation rentals for every style
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Popular amenities for Sheffield pet-friendly home rentals
Pet-friendly house rentals

Entire lake house to yourself. Great for groups
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!

Eclectic one-bedroom house
It’s a really quirky place, perfectly situated for town and for trails. The kitchen is really well equipped, it feels like staying in someone else’s house, but they aren’t there! We really loved having the lights left on for us when we arrived. That made for a warm welcome.

Welcome to The Boathouse! Waterfront/Boats/Hot tub
We stayed here right after our wedding in Westchester county as a "mini-moon" for a couple of days and absolutely loved it! It was the perfect place to relax especially on the patio overlooking the water and the hot tub was an added bonus. This is one of the few Airbnbs we have stayed in that we would go back to in a heartbeat. Beautiful!!! Highly recommend :)

Cozy Kingston home on 1 acre! Kid & Pet Friendly
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!

Bluff House
AMAZING HOME!! Concept design home, very well furnished. We loved all the personal elements it had! The location is great and the hike down to the water was perfect. Highly recommend booking this escape!

Beautiful Fall cabin, North Catskills/Greenville
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! :)

Rabbit Run in the heart of Stockbridge Village
Our family had a great time staying in Anneke’s house in Stockbridge; it had everything we needed and was very comfortable! The fenced yard was also great for our dog. Anneke checked in with us several times during the trip and was very responsive. Highly recommended!

Upland Meadow Retreat - 3 bedrooms/2 baths
Madeline was easily accessible and the well-stocked house was snug, warm, and comfortable during our stay in very wintry weather. The setting is quiet, but very close to town and all amenities. We had a thoroughly enjoyable stay.
Pet-friendly home rentals with a pool

Private lakefront home, hot tub & resort amenities
This property was fantastic. The lake is beautiful, the kayaks and canoe offered by Vincent were in great condition and easy to use to explore the lake. And the house is well decorated, comfortable, and fits a large group easily. I would highly recommend a stay. Vincent is a great communicator and made the whole process easy — zero hassle whatsoever along the way.

Tranquil Cottage in the Country
Pictures don’t do justice! Craig’s place was lovely, from the amazing kitchen to the spacious living room and the outdoor patio. For a group getaway this is the perfect place. Would stay here again in a heartbeat!

Enchanting Upstate Cabin w Pool, Firepit
Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.

Charming apartment with breathtaking view!
Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.

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

Eco Cottage in the Woods
Upon entry, my architect husband said "Cute Cottage; Susan you did it again." Plenty of room for a couple in their mid-seventies, and a Millennial daughter. The cottage is very well insulated such that I didn't have to run the heat except for fifteen minutes at bedtime in mid-October, yet there is a big south-facing sliding door in each of the rooms where the sun and moon shines through. Beautiful woodland falls away from the cottage and small patio beyond the sliding doors, and moonlight is magic on all the leaves. If we had more time we would have investigated the many books in the shelving. We will find excuses for coming back to the area and will stay here again.

Modern Upstate Cabin, near Rhinebeck NY
Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.

Country Getaway Tiny House in Woods w/Pool/Sauna.
House was very clean and comfortable. Loved the decor and bed was super comfortable and cosy. Everything was there in the house- kitchen, bathroom, hot water. Well styled decor. Spotless. Felt very private and peaceful. Location was not as picturesque as I prefer, but fairly close to sight seeing.
Private, pet-friendly home rentals

Mountain Ridge Retreat Getaway
Our stay at Stephen's home was truly amazing. We thoroughly enjoyed the beautiful property and the excellent amenities provided. The home was very spacious, and my family particularly loved the open concept living room and kitchen, which allowed us to easily connect and enjoy each other's company. I would highly recommend your home to anyone seeking a peaceful getaway with a serene outdoor space. Thank you for a wonderful experience.

Chic, ground floor spacious , townhouse hideaway
Stayed at Val's place for 4 months. We were very happy here, it's extremely spacious and the furniture is very comfortable. Plus, it has everything you will ever need during your stay from a screw driver to cheese grater which is often hard to find in rentals and you end up having to buy extra supplies if staying for an extended period of time like we were. The Location is perfect, a few minutes walk to Warren Street and 5 min drive to Fairview Ave. Host is so helpful and responsive. Five + stars. Thank you Val!

Mountaintop Skyloft
The loft was lovely: fireplace, large balcony, view down the mountain, TV with airplay support, kitchen, etc. the surrounding was quiet and peaceful. The host was responsive and very friendly. Would recommend to others.

Lilac House- It's for the Birds
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.

Modern 3BR w/Game Room minutes to HITS, Hunter
We had a great stay, very open and spacious. Everything was clean and the large open kitchen was really nice! Also the yard w deck and fire pit were great!!!! Would definitely recommend, short drive to Woodstock and many trailheads.

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill
This was a very private and peaceful place to stay. Sourabh was a great host who was attentive and made the process smooth and easy. The dome house allowed for amazing views of the stars and the woods. If you want a peaceful and quiet getaway from the city, definitely come here.

2 bedroom / Office - HEPA Air Purifier
Orna was so welcoming and easy to communicate with. The apartment is cozy and well appointed. We were visiting our daughter and family for Thanksgiving. They recently moved to Kingston . Great location! This would not affect most people, but my 90 year “young” dad was with us, so the old fashioned tub/shower was a bit of a hazard for him. Really a gem of a place if you are traveling through or visiting loved ones in Kingston.

Historic farmhouse escape on 14 scenic acres
We really enjoyed our stay at this lovely house!! So many cozy nooks and Miles and Ruth were very responsive and helpful hosts! Would definitely stay again :)
Quick stats about vacation rentals that are pet-friendly in Sheffield
Total rentals
30 properties
Nightly prices starting at
$138 CAD before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Hunter Mountain
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Six Flags New England
- Albany Center Gallery
- Berkshire East Mountain Resort
- TPC River Highlands
- Taconic State Park
- Thunder Ridge Ski Area
- Walkway Over the Hudson State Historic Park
- Bushnell Park
- Zoom Flume
- Mount Greylock Ski Club
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Beartown State Forest
- Naumkeag