Holiday rentals in Stockbridge

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Top-rated holiday rentals in Stockbridge

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Top guest favourite
A red barn-style structure features a white metal roof and is surrounded by a green lawn. Large windows are situated on both sides of the central door, offering views of the vibrant autumn landscape in the background.
Place to stay in Chittenango
4.98 out of 5 average rating, 173 reviews

Luxury Barn Apartment with Private Hot Tub

Come and enjoy the quiet of our newly finished country apartment! Relax and unwind in the hot tub on your private deck, overlooking the beautiful hills of Central New York. A seven minute walk will bring you to Chittenango Falls Park with it’s majestic waterfall and lots of trails. The property is backed by the NYS walking trail that follows an old rail line. The historic Village of Cazenovia is four miles away. Hillside has everything you’ll need for a quiet getaway. Good dogs allowed. No cats.

Guest favourite
A well-lit bedroom features golden walls complemented by white wainscoting. A spacious bed is adorned with a green blanket and a floral throw. An antique dresser is positioned against the wall near a window partially covered by gray curtains. A chair and lamp provide additional seating.
Flat in Munnsville
4.93 out of 5 average rating, 351 reviews

4 Bdrm Apt@Colgate Hamilton Morrisville Bouckville

Minutes to Colgate & Morrisville- Spacious 4 Bedroom, Full Bath, Kitchenette & Spectacular Views Apt. Nicely appointed modern conveniences blended with timeless comfy cozy country charm for a relaxing peaceful productive stay. 28X+Superhost, 750+ reviews & hassle-free self-check in & flex cancel. Clean quality lodging for a fair price in the Middle of Everything! Why overpay for a marginal noisy College Hotel/Inn when you can stay with the most reviewed Airbnb Hosts in CNY at Bearpath Lodge.

Top guest favourite
A spacious kitchen is featured with rich wooden cabinetry and dark countertops. Stainless steel appliances, including a refrigerator and stove, are visible. A central island with bar stools provides additional seating. Decorative tiles enhance the backsplash, while a cozy rug adds warmth to the tiled floor.
Flat in Cazenovia
4.94 out of 5 average rating, 157 reviews

Home Away From Home

Home Away From Home is 850 square feet, 2 bedrooms w/ full kitchen, bath, laundry, newly done. We are close to beautiful views, and nice restaurants.Cazenovia Lake has parks, boating and swimming. Close to down hill and cross country skiing, The links walking trails, winery, brewery , distiller. Colleges include Cazenovia, Morrisville, and Colgate, and only 25 miles to Syracuse University. Couples, solo adventurers, business travelers, and even small families will find solace here. Welcome!

Top guest favourite
The kitchen features wooden cabinetry and ample counter space. A dining table is positioned with several wooden chairs. Appliances include a gas stove, microwave, and dishwasher. Natural light enters through a window above the sink, with a door leading to the outside.
Home in Verona
4.93 out of 5 average rating, 146 reviews

House next door - closest Airbnb to the casino

Bring the whole family to this great place with lots of room for fun. This 2 bedroom, 1 1/2 bath ranch has an open layout with the kitchen, dining area, and living room all open to one another. The master bedroom is huge with a newly installed king size bed, desk, and comfortable chair. The master bathroom has a shower with seat, no tub. The master bathroom can be accessed from the hallway as well. The second bedroom has 2 twin beds. The couch in the living room has a pull out bed as well.

Top guest favourite
A retro-style kitchen features black and white checkered flooring and red accents. A compact counter is equipped with two stylish red stools. Wall shelves display vintage Coca-Cola memorabilia, while a small microwave and fridge are included for convenience.
Guest suite in Clinton
4.97 out of 5 average rating, 769 reviews

The Main Street Market- I-90 (Utica/ Rome)

Located in the Hamlet of Clark Mills, Town of Kirkland, we are centrally located between Utica and Rome approximately three miles from the NYS Thruway. Within a ten to fifteen minute drive you can travel to Utica College, Hamilton college, SUNY Poly, and the up and coming Nano Center. This area is unique for many small family restaurants with many options for local shopping. A short drive away are day trip options including the Baseball Hall of Fame, Syracuse, and the Adirondacks.

Top guest favourite
An inviting living area features large windows that allow natural light to fill the space. A neutral-toned sofa and seating chairs are arranged around a central area rug, while a stone fireplace adds a rustic touch. Greenery can be seen through the windows, connecting indoors and outdoors.
Home in Skaneateles
4.99 out of 5 average rating, 187 reviews

Sunset House- Beautiful Home with Gorgeous Vistas

Experience a home full of windows and light that take in breathtaking views from every angle. You feel like you are on top of the world surrounded by beautiful rural landscaping that is only 1.8 miles from the charming Village of Skaneateles! Lovely interior furnishings with your comfort in mind. You are within close reach to the Skaneateles Polo Fields, a free public boat launch, Skaneateles Country Club, wedding venues and a winery. This newer home is fresh, clean and cozy!

Top guest favourite
The exterior of a charming two-story house features a light beige siding and a slanted gray roof. A welcoming porch with decorative white supports is visible, adorned with hanging plants. Well-maintained greenery and flower beds enhance the inviting appearance of the property.
Flat in Vernon
4.98 out of 5 average rating, 220 reviews

Sleep in Comfort II /Price per person rate

This listing is on the second floor so there are about 15 stairs to climb.The Price is set per person. It is located a half mile from Dibbles Inn and 4.7 miles from Turning Stone Casino. This is a full apartment for guests to stay a day or a week. It has a full bath, full kitchen including refrigerator, stove, dishwasher, microwave, toaster, toaster oven, Coffee machine with coffee caddy. There is are two bedrooms with a queen and a full size bed. Both couches recline (4).

Guest favourite
A white farmhouse with classic black accents is set against a backdrop of lush green grass and trees. The two-story building features a welcoming front porch and large windows, while a distant church spire can be seen through the trees.
Farm stay in Cortlandville
4.96 out of 5 average rating, 163 reviews

1820's Quaint Rustic Farmhouse

Beautiful, spacious, two-bedroom private suite. The Farmhouse is located on 50 acres of farmland in our beautiful river valley. We are directly off the Cortland I-81 exit and are 30 minutes to Cornell, Ithaca and Syracuse. We are conveniently located near Greek Peak and other local ski areas. Great location for professors, parents, students, outdoor enthusiast and anyone exploring the Finger lakes! We hope you enjoy your stay and come back again.

Top guest favourite
The exterior of the apartment showcases a charming two-story building with light-colored siding and a welcoming entrance. A stone pathway leads to the steps, surrounded by neatly maintained greenery. Tall trees provide shade, enhancing the peaceful setting, with a grassy area visible in the foreground.
Flat in Oneida
4.93 out of 5 average rating, 120 reviews

Cardinal Garden Retreat- 2BR Apartment

Welcome! We would love to host you in our cozy, inviting apartment. It’s the perfect spot for up to four guests to unwind and feel at home. Enjoy your own private entrance and plenty of space to relax. Whether you’re here for work, a family getaway, a wedding, or just exploring the area, we’re here to make your stay as comfortable and memorable as possible. Feel free to reach out with any questions—we’re always happy to help! ***Newly updated***

Top guest favourite
The entrance to a rustic cabin is framed by logs, featuring a welcome sign and a seasonal wreath on the door. A pair of wooden rocking chairs sits on a spacious porch, accompanied by a decorative pumpkin and a carved wooden stump.
Cabin in Cooperstown
4.98 out of 5 average rating, 133 reviews

An Upstate NY getaway treasure!

Take it easy at this unique and tranquil getaway. For several hundred years our family has been a part of the Cooperstown community and we look forward to sharing it with you! On over 20 acres of land , you can explore the beautiful landscape of water and woods. Just over the hill from Otsego Lake. Only 3.9 miles (8 min) to Cooperstown’s Main Street in the spring, summer and fall and 5.7 miles (10 min) in winter.

Top guest favourite
The exterior of the A-frame glamp is shown, surrounded by lush greenery and tall trees under a blue sky filled with gentle clouds. A large window reflects the natural scenery, enhancing the connection to nature. The interior view captures a distinctive moon-shaped light fixture suspended from the high ceiling, complementing the triangular architecture.
Place to stay in Oneonta
4.99 out of 5 average rating, 287 reviews

Creekside of the Moon A-frame Cabin

Creekside of the moon A-frame glamp. Float, fish and play in the Catskills. Glamp on the Charlotte Creek in a newly built modern tiny a-frame. Sleep under the full moon. A giant moon light hangs over the bed(s) with a stunning reflection in the window at night over the creekview. Perfect for a romantic getaway, fishing trip, or glamping spot in the Catskills. Close to Cooperstown, NY IG @aframe_moon

Top guest favourite
Lush, vibrant trees display autumn colors reflecting on the calm waters of the lake. A serene shoreline is visible, dotted with boats, while two graceful sculptures of herons stand in the foreground, enhancing the tranquil lakeside setting.
Flat in West Edmeston
4.97 out of 5 average rating, 290 reviews

Blue Heron Lake House on Gorton Lake

Come and enjoy the peaceful tranquility and relaxation at the Blue Heron Lake House, 2876 West Lake Road on Gorton Lake, West Edmeston, NY. We offer an open concept efficiency apartment on the first floor with full kitchen, full bathroom, 2 beds (1 King, 1 full), TV and wifi, sitting and dining area, all with direct access to the lake. We have a whole house generator in case of a power outage.

Popular amenities for Stockbridge holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Madison County
  5. Stockbridge