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Holiday rentals in Sheffield

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Popular amenities for Sheffield holiday rentals

Other great holiday rentals in Sheffield

Top guest favourite
Guest house in Greensboro
4.98 out of 5 average rating, 49 reviews

Cozy retreat in Northeast kingdom Greensboro VT

MadelaineRating, 5 stars2 weeks ago
We had a wonderful stay, the views are amazing and it’s close to mountains and the lake. We were staying in the area for a wedding and enjoyed a peaceful cozy retreat here. We loved the decorations and little details inside and outside. We’re looking forward to coming back and bringing our own pup to meet friendly fluffy Sunny!
Top guest favourite
Home in Craftsbury
4.97 out of 5 average rating, 77 reviews

Relaxing Craftsbury Retreat

BrianRating, 5 stars1 month ago
We have stayed at Neal’s place multiple times in the spring and fall, and have always found it to be convenient and cozy. This time, unexpected snow and a town-wide power-outage made the propane fireplace, battery-powered lantern, and handheld flashlight more than just ambiance-enhancers! They were peace-of-mind enhancers! Thank heavens we had received our Chicken Confidential sandwiches at Black Bird Bistro (a MUST every time we’re in town!) five minutes before the outage. Vacation saved!
Superhost
Guest suite in Burke
4.79 out of 5 average rating, 70 reviews

Convenient Burke 1-bedroom guest suite

SophieRating, 5 stars1 month ago
Lovely spot convenient to the Kingdom Trails network
Guest favourite
Tiny home in Wolcott
4.96 out of 5 average rating, 100 reviews

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit

NatalieRating, 5 stars2 weeks ago
We loved staying at the caterpillar house! We only stayed one night as it was our first stop on a 2 week road trip of the east coast. The home was absolutely adorable, incredibly well designed, and spotless! Check in was a breeze, even tho we got there late at night. Definitely would return and would recommend this tiny home to anyone traveling in the area!
Top guest favourite
Guest house in Walden
5 out of 5 average rating, 18 reviews

Michaud’s Homestead Stay

KaylaRating, 5 stars3 weeks ago
We had a great time staying here! The house was very spacious with lots of light and the view of the farm was so beautiful. It was fun looking out and seeing the cows. Michael was a wonderful host and we would love to return. While in the area we stopped at Hill Farmstead, The Cork & Fork, and the Village Restaurant.
Guest favourite
Cabin in Caledonia County
4.96 out of 5 average rating, 55 reviews

Picturesque Cabin Retreat in the Northeast Kingdom

AubreyRating, 5 stars3 weeks ago
Tina and Stephanie are extraordinary hosts who’ve infused every detail of their stunning Vermont cabin with thoughtful care and creativity. From the moment you step inside, you’ll find yourself drawn to the artful décor, the curated reading nooks, and the countless little discoveries tucked into each corner. Set against a backdrop of serene woodlands, every piece of furniture invites you to sink in with a good book—or drift off to a blissful nap—while the gentle breeze and bird song work their magic. We arrived for a mountain-biking getaway but found ourselves lured back to the cabin’s cozy comforts time and again. If you’re looking for a peaceful, character-filled retreat—or simply a place to unplug and recharge—this is it. And as an unexpected delight, Tina and Stephanie’s warm hospitality and engaging conversation make the experience truly unforgettable. Highly recommended!
Top guest favourite
Guest house in Burke
4.96 out of 5 average rating, 97 reviews

Farm Stay in Burke at Firefly Farm

BeccaRating, 5 stars4 days ago
We had a wonderful stay at Ben’s place. Everything was exactly as advertised and very cozy. The location was close to everything we wanted to do while in the NEK. We hope to be back soon! Becca N
Guest favourite
Home in Sutton
4.92 out of 5 average rating, 49 reviews

Kingdom Carriage House Est. 1842

DinaRating, 5 stars2 months ago
My family had a fabulous time at Israel’s place. The getaway was just what we needed to bond and recharge. Using the hot tub under the stars with snow on the ground was a truly magical experience. We spent our lazy days sitting by the fire, playing board games and cooking as a family. We did take a trip to Lake Willoughby for a hike. It was amazing. It reminded me of a Norwegian fjord. Five stars all around. I would definitely recommend and would rent again in the future from Israel.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Caledonia County
  5. Sheffield