Holiday houses in Dorset

4.97 out of 5 average rating, 108 reviews

Guesthouse in Salem

Guest House at Hummingbird Hill

Our small above-garage guesthouse on the New York-Vermont border is a retreat from busy life. The open floor plan, airy apartment has windows on all sides & overlooks woods, meadow & animal pastures. The guesthouse is ideal for those looking to get away from electronics and the internet, and hike and bike the area’s trails, and/or paddle the Battenkill River and area lakes. Or just sit on the deck with a book and cup of tea or glass of wine. Pets are welcome (we do charge a small fee for pets)!

4.8 out of 5 average rating, 203 reviews

Guesthouse in Manchester

Glamping Cabin with Private Pond and Mountain View

This little glamping cabin with cozy woodstove is set at the far edge of a field overlooking a wildlife pond, seasonal fountain, and mountain. It is a peaceful place, surrounded by beauty, and special not just for these amenities but because it is improbably located on four private acres right in Manchester Center. The property abuts 70 acres of preserved land, but is steps from Main Street and all the shopping, dining, and outdoor options that this lovely year-round tourist town has to offer.

4.99 out of 5 average rating, 188 reviews

Apartment in Dorset

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 4 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

4.9 out of 5 average rating, 907 reviews

Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

4.99 out of 5 average rating, 257 reviews

Apartment in Manchester

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio, but you can enjoy the outside seating set in front of the house.

Guest suite in Manchester

4.91 out of 5 average rating, 144 reviews

Bright Manchester Studio with Sleeping Loft

Our studio apartment with sleeping loft is great for two adults or a couple with children. Located on a quiet country road great for taking long walks. There is a queen bed in the loft and a pull out queen sofa in the living area. Bright with high ceilings and all new furnishings. We are less than three miles from town, 20 minutes to Bromley and 25 minutes to Stratton. Close to hiking, biking, fishing, great restaurants and shopping. Please note;Owners lives on premise in main house.

Guesthouse in Wallingford

4.98 out of 5 average rating, 697 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

4.98 out of 5 average rating, 182 reviews

Cabin in Granville

Quaint log cabin nestled in the woods

Enjoy a break from the daily grind at this lovely tiny log cabin nestled among beech and ash trees. This tiny cabin provides peace and quiet on nearly 4 wooded acres just minutes from the town of Granville, NY. A full kitchen, living room, one bathroom and a loft bedroom complete with stackable washer/dryer provide a place to relax and soak in nature. The spacious front porch grants a protected outdoor space to watch the wildlife and enjoy the fresh air with your family and pup.

4.9 out of 5 average rating, 181 reviews

Guest suite in Dorset

Guest Suite in historic 1804 tavern, w/ Breakfast.

You'll have the whole 3rd floor to yourself with a new private bath, large bedroom with a/c, and a separate sitting room/library. Stay in an historic gem, listed on the National Register of Historic Places. Historically sensitive restoration has been done. You'll have a continental breakfast in the house's original dining room. We're a four a minute drive from the center of historic Dorset village.

4.87 out of 5 average rating, 142 reviews

Bus in Granville

Serene Bus Getaway Among Rolling Farm Land

Tucked off a quiet dirt road, this stationary bus promises to provide you and yours an unforgettable accommodation for your next Upstate NY retreat. Come stay in the Sleepy Tire, and wake up to beautiful views of Vermont’s Green Mountains, an indoor bathroom with flushing toilet and hot shower, and WiFi so you can stay connected to those that matter.

4.99 out of 5 average rating, 112 reviews

Guest suite in Salem

Hilltop Country Views Studio Apartment

Enjoy a relaxing stay in the country. Easy access to Vermont & Saratoga. Eat local produce. Fresh eggs, bread and butter or oatmeal for your first breakfast, coffee and tea provided. Go shop, ski, hike or stay put & enjoy a good book! (After you're confirmed, please let us know if you're vegan, and or glucose or lactose intolerant.)

4.83 out of 5 average rating, 131 reviews

Apartment in Dorset

Peace Street Guest Apartment

2 bedroom 1 bath upstairs apartment with private entrance. Beautiful garden and coy pond with a back drop of Cutler Forest. Hiking trails and trout river walking distance. Close to all amenities: Dorset bakery, golf course, general store, and dining. 10 minutes to Manchester Center shopping.

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Other great holiday rentals in Dorset

4.87 out of 5 average rating, 91 reviews

Apartment in Dorset

Cozy two bedroom near Manchester

KalienaRating, 5 starstoday

The host was helpful and kind. The space was exactly what we needed for a weekend soccer tournament! Clean, quiet, comfortable, and in close proximity to the fields. We had a great stay!

4.93 out of 5 average rating, 40 reviews

Apartment in Manchester

Manchester Cottage

AlessandraRating, 5 stars2 weeks ago

Had a wonderful stay at this charming guest suite. It has great amenities, with a full kitchen, and is very centrally located. It is kept very tidy and clean, and we really appreciated the flexibility with checking in/out. Our host was very responsive and attentive. It was perfect for us, and we'd love to stay here again!

4.97 out of 5 average rating, 31 reviews

Cabin in Cambridge

Pond View Cabin. Off-Grid, Rustic & Dog Friendly.

EmilyRating, 5 stars2 weeks ago

Highly recommend Brian’s off grid cabin! His directions were very helpful and made navigating the generator, camp shower, and other on-site details super easy to understand and execute. His property is beautiful and peaceful. We’re already looking at our calendars for another time to visit. Our dog, Stumpy, very much enjoyed the outdoor access and pond. He didn’t want to leave!

5 out of 5 average rating, 51 reviews

Cabin in Manchester

Private Rustic Modern Loft

Michael & PaulaRating, 5 stars1 month ago

Came to town to see Palmyra and Joseph Terrell play a house show at Billsville. Lucas’ place was right around the corner which was very convenient. The loft was cozy, spacious, well equipped and the bed was very comfortable. Lucas was responsive to our questions. Would definitely stay here again if the opportunity arises.

4.93 out of 5 average rating, 15 reviews

Home in Dorset

Creekside Mid-Century Escape

MadelineRating, 5 stars2 months ago

David’s home was a wonderful getaway! It was incredibly comfortable, with a beautiful setting and the soothing sound of the water right off the deck. The space was clean, spacious, and well-maintained, making our stay even more enjoyable. We truly appreciated the peaceful atmosphere and can't wait to return!

4.99 out of 5 average rating, 79 reviews

Apartment in Manchester

Cozy Apartment on Private Road

GregoryRating, 5 stars3 months ago

Our family had a wonderful weekend at Linda’s apartment. The location was perfect with convenient access to skiing and the town of Manchester. The apartment was immaculate and very comfortable. Linda was extremely hospitable and helpful. I hope we have an opportunity to stay there again. Thank you, Linda, – we really appreciate your kindness and hospitality.

4.91 out of 5 average rating, 67 reviews

Cabin in Winhall

A frame cabin with Hot tub near Stratton, VT

Samantha Rating, 5 stars1 week ago

my 2 best friends stayed the weekend for my 30th and it was amazing, a dream home, so very peaceful. all of us are moms, and this place was so relaxing and we will definitely be back. Christina even left a bottle of bubbles which was just what we needed. she is an amazing host