Holiday rentals in Dorset Hill

4.94 out of 5 average rating, 348 reviews

Cabin in Londonderry

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Guest house in Manchester

4.8 out of 5 average rating, 204 reviews

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

Flat 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

Guest house 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

Flat 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.

4.94 out of 5 average rating, 1,269 reviews

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Guest house 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.

4.99 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

Flat 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 Hill

5 out of 5 average rating, 37 reviews

Barn in Manchester

Bromley Barn

AndrewRating, 5 stars2 months ago

We had the best stay at Frank and Diane’s place. It was so beautiful and clean with everything we needed. We kept saying “we can’t wait to get back to the Airbnb”. It was so cozy and the pool table was the perfect activity after hitting the slopes. You can’t ask for better hosts than Frank and Diane. Between Frank greeting us when we arrived, their sweet dogs Molly and Percey, the delicious blueberry muffins and our shared hometown connection we felt right at home. We can’t wait to visit again next year and will definitely tell our friends about this great find!

4.87 out of 5 average rating, 91 reviews

Flat in Dorset

Cozy two bedroom near Manchester

KalienaRating, 5 stars1 day ago

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!

4.82 out of 5 average rating, 34 reviews

Townhouse in Dorset

Mountain House (VT Summer Horse show/mtn biking)

VladlenaRating, 5 stars7 months ago

We visited Vermont with our two kids for foliage and stayed at Galina's house. Check in was very easy, house is located on the top of the mountain and has beautiful views, at the same time it is very close to all kinds of restaurants and cafes. We loved the area, took a hike straight from the house to the caves, hike from the house to the lake is about 1 hour each way. We explored local restaurants in Manchester and Dorset and even checked out some galleries and Southern Art center. Kitchen had everything we needed, even bread maker. Our kids enjoyed pinball pastime in Manchester with antique arcades machines and local farms withe fresh cow's milk and eggs. Late nights were spend by the fire pit, roasting marshmallows. The whole family enjoyed the stay and the house up in the mountains.

5 out of 5 average rating, 46 reviews

Guest suite in Dorset

Private Retreat Steps from Dorset Village Green

RachelRating, 5 stars5 months ago

I can’t say enough wonderful things about our stay in Dorset at Anne and Neil’s place. We stayed for two nights over New Year’s Eve and had the best start to 2025 in their comfortable, cozy, and thoughtfully designed guest house. We enjoyed the homes’ close proximity to hiking trails/nature and also the quaint historical town of Dorset. Anne and Neil provided local recommendations for restaurants and reservations to get in advance which were wonderful. We slept great in their King sized bed with luxurious bedding. Run, don’t walk to book your stay in Dorset at Anne and Neil’s home!

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.

4.99 out of 5 average rating, 79 reviews

Flat 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, 68 reviews

Cabin in Winhall

A frame cabin with Hot tub near Stratton, VT

MeganRating, 5 stars1 day ago

Had a lovely couples weekend getaway at this airbnb! The place was very cute and cozy with a nice large kitchen - we enjoyed making meals together and there was plenty of space for all of us. It really nice to have a separate bathroom for each couple and the bedrooms were comfy with a really nice bathtub setup upstairs! The location was great - we did some hiking nearby and it was very quick to drive into the town and get groceries. Overall, had a great stay and would highly recommend staying here!