Vacation rentals in Berkshire

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Top-rated vacation rentals in Berkshire

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

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Top guest favorite
A cozy sleeping area features a spacious bed adorned with soft linens and a warm throw. A large window showcases expansive views of Seneca Lake under a blue sky, while a flat-screen TV is mounted on the wooden wall, complementing the cabin's rustic charm.
Tiny home in Burdett
4.99 out of 5 average rating, 136 reviews

FLX 2-Lake View 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 favorite
A cozy living area features a plush sofa, warmly illuminated by nearby lamps. A stone fireplace is centrally positioned beneath a mounted television. Natural elements are introduced with hanging plants, and a wooden coffee table is placed atop a vibrant area rug.
Chalet in Ithaca
4.97 out of 5 average rating, 476 reviews

Naturalists' Retreat

Retreat to paradise at this cozy cottage in the heart of the Finger Lakes. Charming custom woodwork offers a unique, rustic aesthetic while modern amenities provide the comfort of home. Minutes from famous naturalist attractions in all directions. Enjoy the entire peaceful cottage and surrounding yard with outdoor seating, fire pit, and hot tub to yourself. Three acres of adjoining trails and creek shared with neighboring host family, who are fun-loving and approachable but respect your privacy.

Top guest favorite
A spacious living room features two comfortable gray sofas and a decorative coffee table, positioned around a large screen TV. Natural light filters in, enhancing the warm tones of the walls. A small side table with a lamp adds to the cozy ambiance.
Apartment in Greene
4.98 out of 5 average rating, 185 reviews

New Downtown Greene Apartment *no cleaning fee!*

This spacious one bedroom apartment overlooks peaceful downtown Greene. A quaint little village known for its unique shops and chic restaurants. This apartment gives you 1000+ sqft of a home away from home, equipped with all the amenities: washer/dryer, full kitchen, living room, bedroom, & off-street parking. This beautifully designed, modern apartment is perfect for the business traveler or family staying for recreational purposes. One bedroom with a pullout couch & air mattress, sleeps 6.

Top guest favorite
A simple exterior view of the tiny house is captured, featuring a metal roof and a garage door. A small lawn area with green grass and two outdoor chairs is present, along with a black barbecue grill. Trees are visible in the background.
Tiny home in Cayuta
4.96 out of 5 average rating, 169 reviews

House on the Hill

A tiny house with the comforts of home. Single Bedroom stair free in-law suite with amazing sunsets and the feeling of being in the middle of the woods while still being close enough to enjoy a reasonable drive to some of the Finger Lakes best hiking trails, food, wineries and other destination locations. If you come in the winter you will want an all wheel drive vehicle if there is snow on the roads, but half a mile down the hill and you are on the state highway to the finger lakes region.

Guest favorite
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, 295 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 favorite
The exterior of a charming yellow bungalow is presented, featuring green trim and red shutters. A welcoming front door is surrounded by greenery, with a small potted plant nearby. A red bench adds a cozy touch to the outdoor space, situated along a stone pathway.
Bungalow in South Hill
4.95 out of 5 average rating, 312 reviews

Ithaca Bungalow/Tiny Home, Quiet Escape in City

Unique, cute, bungalow in quiet spot. Walk to Commons, restaurants, shops, entertainment. Near Ithaca College (.8 miles) and Cornell (1.1). Includes livingroom, bedroom, bathroom, kitchen (full stove, refrigerator, microwave), sunroom, clothes washer/dryer. Queen bed, dresser, closet. Deck and patio in the back. Recreation trail (20 miles of paths, creek and falls), entrance from our street. Bus stop on corner. Driveway in front of bungalow is yours! No through traffic, peaceful.

Top guest favorite
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, 128 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 favorite
The exterior of a newly constructed cabin is showcased, featuring a welcoming entrance beneath a wide porch. A landscaped yard is adorned with mulch and a unique ornamental tree made of twinkling lights. Comfortable seating is positioned on the porch, inviting relaxation.
Cabin in Hector
4.98 out of 5 average rating, 126 reviews

Wine trail Cabin with a view Cabin 3

Keep it simple at this peaceful and centrally-located place on 50 acres. New construction Located between the Seneca and Cayuga lake wine trail. 15 minutes from Watkins Glen and 30 minutes from Ithaca. 17 wineries and 5 breweries within 5 miles of the cabin. Relax on the patio with your wine and watch the sunset over the lake. Bald eagles frequently fly over so Keep your eye on the sky. There’s a back up generator if there’s a power outage. It will kick in automatically

Guest favorite
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, 320 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 favorite
The exterior of a modern tiny house is depicted, featuring a blend of wood and metal materials. Large windows provide natural light, while a spacious deck extends from the front. Surrounding greenery enhances the rural setting, emphasizing a connection to nature.
Tiny home in Ithaca
4.97 out of 5 average rating, 309 reviews

Not-So-Tiny House: Country Charm, Modern Feel

Find your oasis in this stylish tiny house on the outskirts of Ithaca. Explore the outdoors with 85 acres of woods, pastures and ponds with wide trails great for hiking and cross country skiing! Fire up the grill and dine al fresco on one of three decks, then warm up by the fire pit. Enjoy the quiet of the natural surroundings while remaining a stone's throw away from Ithaca's many attractions including state parks, dining, universities, wine trails and more.

Top guest favorite
The entrance to a timber frame cottage is framed by tall trees, featuring a wooden door with a simple black handle. Cozy seating is provided on the porch, adorned with colorful decorative bunting and string lights for a cheerful touch.
Cottage in Candor
4.97 out of 5 average rating, 288 reviews

Tiny, romantic, timber frame

Unplugged (no WiFi) and peaceful. We provide breakfast foods. Unfortunately we cannot provide fresh breakfasts at this time, to keep our prices the same, with inflation. We hope to again in the future, if the current costs go down. A family built, tiny, timber frame. We are in a farming community, and several Amish farms dot our road. Please drive slow for children and animals. Please book both weekend nights during weekend stays, May-Oct. Thank you!

Guest favorite
A handcrafted wooden yurt is nestled among trees, featuring a welcoming door and steps leading to its entrance. Two red Adirondack chairs are positioned nearby, providing a tranquil seating area amidst the surrounding greenery and wildflowers.
Tiny home in Interlaken
4.99 out of 5 average rating, 336 reviews

Walnut Grove Yurt at Finger Lakes Cider House!

Welcome to The Walnut Grove Yurt! Our original yurt at Finger Lakes Cider House. This handcrafted yurt is an all-season, round, wooden cabin nestled creek -side in our walnut grove. Every detail is custom built by our Cider House crew. This little hobbit house sits on our 70 acre property of regenerative pasture, forest, and apple orchards— shared with our grass-fed flocks and herds of turkey, chicken, pigs, sheep, and white angus.

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