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Vacation rentals in Berkshire

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Berkshire

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

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Top guest favourite
A charming cottage is framed by vibrant pink rhododendron blooms, creating a striking entrance. A pathway of circular stepping stones leads from the grassy area to the front door, surrounded by lush greenery.
Tiny homes in Oxford
4.97 out of 5 average rating, 382 reviews

⭐Wildflower Country Cottage

🏡 Cozy cottage in the countryside. Gardens galore to explore! 🏘 Less than 5 minutes from town 🎟 Many local attractions including: 🦒 Animal Adventure 🏎 Northeast Classic Car Museum 🥾 State Parks, and hiking trails 🚶‍♂️Enjoy an afternoon in the gazebo or take a stroll around any of the many garden paths. 📕 See our guidebook for our favorite local attractions and eateries. ℹ️ Please check out our other listing: Lakeside Reflections https://airbnb.com/h/lakesidereflections

Top guest favourite
Tiny homes in Burdett
4.99 out of 5 average rating, 183 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!!

Guest favourite
Guest suite in Lansing
4.95 out of 5 average rating, 262 reviews

The Lakeview Nook – Midcentury Modern Stay

Enjoy this mid-century modern guest house in a spectacular site, with a lake view, waterfall, and forest all in one place. The house was just fully renovated. This house is just 2 miles from Ithaca downtown and 3 miles from Cornell University. The location is super close to everything Ithaca has to offer—Ithaca falls, downtown, restaurants, the farmer's market, wineries, all within a few minutes drive of your rental. This unit is fully private, with no shared areas/entrance with the other unit.

Top guest favourite
A charming bedroom features a wooden bed topped with a floral-patterned blanket. An antique dresser with a marble top stands adjacent to the bed, accompanied by a vintage mirror and decorative items. Natural light filters through the room, enhancing the rustic ambiance.
Barn in Ithaca
4.88 out of 5 average rating, 101 reviews

Beautiful barn home in Danby

The house is built into a barn. It has rustic charm and modern comforts. It's situated in a beautiful valley with a lovely view. The back porch and yard are nice places for relaxing. There is a basketball hoop in driveway side. Dwelling is 7 miles from Ithaca , which is about a 15 minute drive. There is is no real public transportation, except for a bus that runs to Ithaca at 8am and 5pm on weekdays. To catch it, walk the half mile to the highway and flag it down. Welcome to the country.

Top guest favourite
A charming cabin is positioned on a grassy knoll, showcasing a wraparound porch with wicker chairs and decorative elements. The structure features a combination of stone and wood materials, with a sloped roof and large windows allowing for natural light.
Cottage in Oxford
5 out of 5 average rating, 404 reviews

Beaver Palace Studios and Estates relaxing getaway

Your total getaway from the city and/or hectic life. We offer a very private and personal space for you to unwind and relax Everything on the property is handmade/built by owners. The grounds are very private. There is an abundance of wildlife and 50+ acres of private grounds to explore. Both owners are artists and world travelers. This stay is casual, relaxing and a real get away from it all. Hosts just down the lane for any assistance. Please book accurately # of people and # of pets.

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
4.94 out of 5 average rating, 163 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).

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, 131 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 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, 326 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, 135 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 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, 289 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!

Top guest favourite
Cabin in Binghamton
4.93 out of 5 average rating, 430 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
Tiny homes in Interlaken
4.99 out of 5 average rating, 343 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.

Popular amenities for Berkshire vacation rentals

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  4. Tioga County
  5. Berkshire