Holiday rentals in Berkshire

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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 elevated treehouse is illuminated by soft lighting along the wrap-around deck, surrounded by trees in a nighttime setting. A gentle slope leads up to the entrance, providing accessibility. The structure features warm wood tones that complement the natural surroundings.
Treehouse in Horseheads
5 out of 5 average rating, 256 reviews

A Treehouse Secluded in Private Forest

A Treehouse. Reconnect with nature at this unforgettable escape. Nestled in 28 acres of woods with hiking trails. This unique newly constructed all electric 525 sq foot elevated structure offers a wrap around deck for an ever changing view. King size bed & new technology foam offers complete comfort in separate climate controlled bedroom. Heated bathroom floor is a “warm” surprise. Optional seasonal outdoor shower for the adventurous. Kitchen lacks nothing tucked conveniently in the great room.

Top guest favourite
Tiny home in Burdett
4.99 out of 5 average rating, 163 reviews

FLX 3- Lake View Wine Country Tiny Cabin

Nestled up on a hill overlooking Seneca Lake, watch the sunset while laying in bed or from your own patio with a fire crackling. We are local hosts and will make sure you have an unforgettable stay! Everything you could want to do in the Finger Lakes will be at your fingertips. Wineries galore, two even just next door, multiple breweries nearby, minutes to the lake, 15 minutes to downtown Watkins Glen, 10 minutes to hiking trails at the national forest, or stay in, relax, and enjoy the view!!

Top guest favourite
A modern studio loft is nestled within a lush green forest, surrounded by tall trees and foliage. The structure features large windows and a spacious deck, providing an inviting connection to the natural landscape. The serene, wooded environment offers a sense of seclusion.
Loft in Burdett
4.97 out of 5 average rating, 138 reviews

Fox Den Studio, Lake View, Location, location!

Fox Den is a fully furnished 600 sq ft studio loft apartment with all the amenities that you could need. Eat out or cook in our kitchenette. The view from your 2nd floor deck is stunning with sunsets that dreams are made of. The loft has high, open ceilings that give you a cottage feel that immediately brings relaxing vibes. Hike our 10 acres of trails next door on our glamping grounds, including a fishing pond Your secluded spot is right in the middle of wine country and state Forest trails

Top guest favourite
A charming white house is nestled among tall trees in a lush green setting. The home features a garage and a front porch with seating, while an American flag gently waves. A gravel driveway leads to the entrance, enhancing the serene, country atmosphere.
Home in Newfield
4.97 out of 5 average rating, 104 reviews

Thee Old Stro House -Newfield

Relax with the whole family, including your four legged friends at this peaceful place to stay. Secluded two bedroom house just minutes away from Ithaca or Watkins Glen. Our house is the perfect place for those wanting a peaceful, private and quiet country experience while still being only 10 miles from Cornell or IC or 15 miles from Watkins Glen. Enjoy Finger Lakes wine tours, hiking trails, gorges, state parks and much more right at your fingertips. Come see what country living is all about.

Guest favourite
A well-appointed bedroom features a spacious bed with soft linens and a decorative blanket. Warm yellow lamps provide light on either side of the bed, and a chandelier enhances the ambiance. A soft area rug lays beneath the bed, adding comfort to the wooden flooring.
Cottage in Whitney Point
4.83 out of 5 average rating, 158 reviews

King size master, high spd internet on the water

Located between Ithaca, Binghamton and Cortland great for college visits, tours of wine/breweries and skiing. The house is set up for sound, enjoy tunes on the deck, back porch and inside. It's clean, comfortable and close to so many things! Kid/dog friendly too. (NO cats) Walk to restaurants, ice cream, grocery, liquor store, playgrounds, BC fairground and village amenities. Close to Dorchester Park, close to kayak/canoe launch and quick highway access. Wired/ethernet speed 300 down 10 up!

Top guest favourite
A gravel driveway leads to a secluded cabin nestled among tall pine trees. Sunlight filters through the branches, casting a warm glow on the landscape. The natural surroundings feature a blend of greenery and autumn foliage, creating a tranquil setting.
Cabin in Lisle
4.95 out of 5 average rating, 308 reviews

Private Cabin and Pond Property

Enjoy our secluded cabin, pond, and picnic area with many acres to roam. Rest comes easy with the privacy and peaceful woodlands that is the setting of our family's newly refurbished vacation space. Up to two Cots available upon request (must bring your own bedding.) Comfortable space for up to 4 guests. Our cozy cabin is the perfect chance to unplug from the busyness of life, equipped with WiFi but very sparse cell reception. WiFi calling feature can be used for important connections.

Guest favourite
A rustic cabin with a red metal roof is situated near a tranquil pond surrounded by green foliage. A large wooden deck extends from the front, offering views of the natural landscape. Stone steps lead from the pond's edge to the cabin, enhancing the serene atmosphere.
Cabin in Vestal
4.84 out of 5 average rating, 297 reviews

324 Knight Road, Vestal, NY

This cabin is a rustic getaway with all the comforts of home. Nestled in the woods, the cabin has an abundance of hiking trails with a covered bridge, and small farm that guests are welcome to visit. From APPROXIMATELY December 1 - March 1, the property is home to a full size sheet of ice. The rink and farm are featured in the 2022 Bauer Hockey holiday catalog. Be sure to bring your skates! A travelling massage therapist may be available for private bookings with a few days notice.

Top guest favourite
The exterior of a rustic cottage is framed by a large tree and vibrant blooming rhododendrons. The building features a sloped roof and multiple windows, blending harmoniously with the surrounding nature.
Cottage in Brooktondale
4.98 out of 5 average rating, 127 reviews

Canaan Country Cottage

This is a private, rustic and cozy vacation camp that has been partially modernized with an addition containing two bedrooms. The original part of the building still has that Adirondack camp feel; woodsy and camp-like, but very private. Secluded and also close to Hammond Hill State Forest with many miles of trails for mountain biking, hiking and xc-skiing. The cottage sleeps 4 to 6. We recently upgraded the internet with a fiber connection, and added a propane grill on the back deck.

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, 154 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 + HBO, and has satellite wifi (30+ MBPS).

Top guest favourite
A rustic cabin features a screened porch and circular turret adorned with large windows. Two red adirondack chairs are positioned on the grassy area in front of the cabin, inviting relaxation amidst the surrounding autumn foliage.
Cabin in Van Etten
4.95 out of 5 average rating, 129 reviews

Gorgeous Hilltop Paradise with epic views and pond

A beautiful slice of nature and unique cabin on 30 acres of land with modern ammenities. Enjoy distant views of hills through huge windows overlooking a swimming pond. It's a retreat for every season, featuring beautiful fall folliage, hiking, cross-country skiing and a lush and picturesque spring and summer. The house features a round kitchen and bedroom with a vaulted ceiling. Enjoy a giant view of the sky, fire pit by the pond, the sound of frogs, meditate, relax, or … work!

Top 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, 321 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
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, 133 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.

Popular amenities for Berkshire holiday rentals

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