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Holiday houses in Berkshire

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Berkshire

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of the uniquely designed guesthouse features a combination of dark siding and large windows, highlighted by colorful fall foliage. A spacious deck with seating is visible, surrounded by potted plants, creating a peaceful outdoor space.
Cabin in Erin
4.99 out of 5 average rating, 316 reviews

Unique Country GuestHouse

Unique country GuestHouse artistically renovated from a repurposed insulated tractor trailer. Private, quiet woodland setting under starry night skies. Brilliantly designed to maximize space for a bedroom- queen bed, desk area. Full bathroom, fully equipped kitchen, eating and lounging area, comfy loft with a sleeper sofa. The spacious sunny deck, shady patio, & fire pit bring your experience more outside. 1.6mi woodland trail. Turkeys, chickens, herb farm. Wifi. 10% discount for repeat guests.

Top Guest favourite
A serene waterfall cascades between moss-covered rock formations, surrounded by lush green trees. The sunlight filters through the foliage, creating a tranquil ambiance. The water flows gently, creating a soft sound that complements the natural setting.
Cabin in Trumansburg
5.0 out of 5 average rating, 110 reviews

Waterfall retreat

Sleep to the sound of your private waterfall in this cabin made for two. 12 miles from Ithaca and central to all that the Fingerlakes has to offer, less than one mile from the only National Forest in New York State, a 15 minute drive to either Seneca or Cayuga lakes, Waterfalls and of course the renowned wine trails. This cabin is equipped with high-speed wifi, climate control with AC, hot/cold water, flush toilet. Fold-out couch in the living room for a third guest (fee). Grown-ups only

Top Guest favourite
A riverside retreat is depicted, featuring a charming blue exterior with the house number displayed prominently. A gravel pathway leads to the entrance, surrounded by green grass and mature trees, with the Susquehanna River visible in the background.
Home in Owego
4.99 out of 5 average rating, 106 reviews

Riverfront Cottage in Owego, New York

Welcome to our charming 2-bedroom, 1-bathroom riverside retreat in Owego, NY! This home is a haven of comfort with an open-concept kitchen, dining, and living room. Step through sliding glass doors onto a large deck, where the Susquehanna River's beauty unfolds before you. Enjoy Owego's revitalized downtown shops and restaurants, or explore the nearby attractions of the Finger lake wineries, the nature trails/waterfalls of Ithaca and Watkins Glen, or the artistry of the Corning Glassworks

Guest favourite
The entrance to 'The Hobbit House' is framed by lush greenery and features a distinctive wooden door in deep red. The charming exterior showcases a combination of shingled textures, with a shaded porch adorned by a wooden pergola and decorative string lights.
Farm stay in Brooktondale
4.92 out of 5 average rating, 121 reviews

Farmstay Scottland Yard-Hobbit House dogs welcome!

Scottland Yard farm stay, 'The Hobbit House' Come enjoy our little piece of paradise. We are located 10 easy miles from Ithaca NY in the beautiful Finger lakes region! we are less than 1/2 day trips from NYC, NJ, PA, Rochester and Buffalo. We have consistently been Airbnb super host for 6 years! We have seasonal glamps and cabins, but are now offering our favorite little hideaway year round! Enjoy the gentle peaceful flow of life just breathing the sweet air here at Scottland Yard Farm.

Top Guest favourite
A charming wooden cabin features a large screened-in porch and multiple windows. A stone fire pit is surrounded by rustic stools, creating a cozy outdoor gathering space. Lush greenery and trees provide a natural backdrop, evoking a serene atmosphere for relaxation.
Cabin in Freeville
4.95 out of 5 average rating, 172 reviews

Hot tub under the stars at cozy cabin in the FLX

Nestled in a grove of Norway spruce, your peaceful cabin getaway rests in the heart of the Finger Lakes. Built by a local carpenter (with help from his dog Indiana), the cabin has enough coziness and charm to make any stay special. Hike down to Mill Creek (on the property), grill up some burgers on the gas grill, or lounge in a hot tub beneath the stars. The cabin is 15 minutes to Ithaca / Cornell, has a living room with a Switch + BluRay + Netflix, and has satellite wifi (30+ MBPS).

Guest favourite
A serene landscape features a calm pond reflecting a colorful sunset sky. A small guest house is visible on the opposite shore, surrounded by lush greenery and trees. The tranquil scene captures the natural beauty of the area.
Home in Newark Valley
4.96 out of 5 average rating, 331 reviews

Private Scenic Retreat

The entire place is yours to enjoy! Our guest house is located on a dead-end road five minutes from the town of Newark Valley and only 30 minutes from Binghamton, Cortland, and Ithaca Included is a kitchen with open common area, two bedrooms, full bath and washer/dryer within living area. A farm setting is viewable from the common area and attached deck. There is a 2 acre pond and miles of scenic trails spread over 250+ acres, with sights as far as Pennsylvania!

Top Guest favourite
Cabin in Hancock
5.0 out of 5 average rating, 59 reviews

Lakefront A-Frame | Hot Tub, Sauna, Fire Pit

Escape to Hancock A-Frame, a romantic lakefront hideaway tucked into the woods of Hancock, New York. Designed for couples, this serene retreat offers direct lake access just steps from the back deck—perfect for swimming, paddleboarding, or launching the canoe right into the water. Relax on the deck with a hot tub, lakeside sauna, grill, and intimate outdoor dining overlooking the lake. Very cozy and surrounded by nature, it’s a perfect year-round escape for two.

Top Guest favourite
A spacious living area features a leather couch with decorative pillows and a wooden coffee table centered on a plush area rug. Large windows provide natural light and views of the surrounding trees. A dining table is visible to the right, enhancing the inviting atmosphere.
Cottage in Freeville
4.99 out of 5 average rating, 140 reviews

Country retreat near Ithaca

Your own comfy, private, immaculately clean 2-story cottage with A/C, full kitchen, dishwasher, full bath, wifi, TV+Roku, washer/dryer, deck, couch, desk, fire pit, grill, and free EV charging. Ideal for relaxing, remote work, or as base to explore the area's restaurants, trails, wineries, and more. Nestled against a wooded hillside, surrounded by trees, meadows, and marshes. Tons of birds and animals. 20-mins east of the Ithaca Commons and college campuses.

Top Guest favourite
The cabin is positioned on a grassy area, with a serene pond visible nearby. The structure features a sloped roof and wooden siding, surrounded by lush green hills. A clear sky at dusk displays the moon, creating a peaceful ambiance.
Cabin in Newark Valley
4.96 out of 5 average rating, 25 reviews

Cozy cabin with pictureous views

Relax at this unique and tranquil getaway. Sit on the deck and watch the Scottish Highlander cows graze (or even feed them by the fence) to watching the Koi fish by the pond u will enjoy the peacefulness of the country. The position of the cabin is ideal for Sunrises and Sunsets that brighten the sky. State Game Lands 1/2 mile away. Also wine trails and waterfalls around an hour away. 20 minutes to Binghamton area, 30 minutes to a casino, 45 minutes to Ithaca

Top Guest favourite
Cabin in Binghamton
4.93 out of 5 average rating, 431 reviews

Cozy/Chic Cabin Binghamton NY

Retreat, isolated get-away but nearby town. This cozy cabin is rustic with some chic flair, decor & recent updates. Privately set on 2 wooded acres & near town. 2 stone fireplaces, indoor Jacuzzi tub, 2 1/2 BA, 3-4 BR & 7 person outdoor hot tub. Excellent WIFI, kitchen & dining. Picnic, grill & fire pit. Great fall foliage, near skiing, near hiking, boat launch. Fully outfitted, just bring yourself!! Willing to accommodate guests—ask!!

Top Guest favourite
A rustic entrance features smooth stone steps leading to double glass doors. Decorative pumpkins and vibrant chrysanthemums in terracotta pots add seasonal color. Wooden Adirondack chairs provide a relaxing spot under a covered porch illuminated by hanging lights.
Cabin in Burdett
4.99 out of 5 average rating, 225 reviews

Fall in Love with this Cabin! Watkins Glen

Enjoy a romantic getaway in this beautiful 1 King bedroom cabin, located in the heart of the Seneca Lake Wine Trail. This newly updated cabin provides all the modern amenities with a rustic country feel. It is set in a meadow with adjacent forest, has a charming fireplace perfect for warming up after a day of exploring, and offers breathtaking night-sky views around the campfire. Located just 2 miles off the Seneca Lake Wine Trail!

Top Guest favourite
Guesthouse in Owego
5.0 out of 5 average rating, 107 reviews

Waterfront guesthouse with beautiful view

Private guesthouse with 1 king bed and no cleaning fee, in the woods overlooking a 3 acre pond on a 30 acre property with trails and nature all around. Constructed in 2023 with sustainability and views to nature in mind. Conveniently located between Binghamton and Ithaca, and a quick 5-minute drive to historic Owego. A quiet getaway to immerse yourself in nature.

Popular amenities for Berkshire holiday rentals