Holiday rentals 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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Guest favourite

Guest house in Ithaca

4.97 out of 5 average rating, 701 reviews

Secluded Free-Standing Cabin in Bucolic Setting

Cozy, comfortable, brick bungalow nestled in a stand of trees offers convenience & seclusion just off the beaten-path. Knotty pine, radiant heating, cathedral ceiling & loft are warm & inviting. Minutes away from 3 state parks, Cayuga & Seneca lakes, wine trails, Cornell, Ithaca College & the renowned Ithaca Commons. **Sorry, Airbnb prohibits booking for another person including "gift bookings." Booking that are gifts must be done so in the name of the guest who will be staying at the property.

5–12 Nov

$184 SGD per night

Guest favourite

Cabin in Erin

4.99 out of 5 average rating, 208 reviews

Unique Country GuestHouse

A unique country GuestHouse artistically renovated from a repurposed insulated tractor trailer. 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. Private, quiet woodland setting under dark night skies. The spacious sunny deck, shady patio, & firepit bring your experience more outside. Wifi. 1.6mi woodland trail. Turkeys, chickens, herb farm. 10% discount for repeat guests.

1–8 Jan

$218 SGD per night

Guest favourite

Flat in Van Etten

4.97 out of 5 average rating, 166 reviews

Finger Lakes Sunset View near Ithaca and Watkins

Escape to our charming, country-chic space, an ideal retreat for two. This private haven has all the essentials for a perfect getaway. Nestled in the beauty of NY’s Finger Lakes, our location is 30-40 mins from diverse attractions: the lively college town of Ithaca, Cornell University, thrilling NASCAR events in Watkins Glen, renowned wineries, & state parks. For those seeking tranquility, step onto the private deck and enjoy a fire as the sun sets. Welcome to your peaceful escape in upstate NY!

9–16 Oct

$165 SGD per night

Guest favourite

Flat in Hector

4.96 out of 5 average rating, 255 reviews

Private Lakefront on Seneca Wine Trail

You’ll enter a Large, Luxurious, Private studio apartment in beautiful Arts & Crafts style. *Located on a Town Maintained secluded lake-side road on the shores of the east side of Seneca Lake. *Ten-foot Coffered Ceilings *On the Seneca Lake Wine Trail. *We welcome visitors all year round. A wonderful option for couples looking for a private, quiet place to get away. *Many custom-crafted details. *2 additional guests can be accommodated with a fold-out sofa bed (an additional fee. )

24 Feb – 3 Mar

$187 SGD per night

Guest favourite

Cabin in Brooktondale

4.95 out of 5 average rating, 140 reviews

Aframe Retreat, Get away without getting far away

Dreamy A-frame tucked away on 5 acres of woodland. Lots of peace and quiet in tranquil lofted areas for yoga, meditation, reading, and writing. Rustic worldly home features wood stove for coziness. Large deck is perfect for outdoor moments. Hop in the car for a local brew at Brookton Market. Just minutes away from the Shindagin Hollow State Forest, a mountain biking mecca. This retreat is a great launching point for skiing, lake adventures, and wine country. check us on insta: aframe_retreat

$233 SGD per night

Guest favourite

Chalet in Willet

4.96 out of 5 average rating, 117 reviews

Lakefront Home; private, with kayaks and canoe

Welcome to the Sunset Chalet - your serene, lakeside getaway! Gorgeous lakefront with lake access, over an acre of private land, and trails to explore! A private swimming pond & fire pits. Free use of 2 kayaks- 2 adult life jackets; and a canoe (Summer time). Rejuvenate with amazing views and hikes. We are conveniently located near Greek Peak Resort Ski Area, and Labrador Mountain. Not far from wine trails, Ithaca, and great hiking. Lots of open space. Relax, and savor the tranquility!

19–26 Oct

$200 SGD per night

Guest favourite

Home in Spencer

4.96 out of 5 average rating, 179 reviews

Cozy new 2 bedroom house near Ithaca

Looking for value and a nice property? Our updated quiet and cozy house is close to Ithaca, Cornell Univ., Ithaca College, Fingerlakes, Watkins Glen, Wineries and State Forests. You’ll love our place because of it's proximity to many areas and the price is very reasonable & NO cleaning fee. Washer & Dryer, flat SMART TV, WIFI, large yard. Perfect place for your next stay in the Southern Tier/ Fingerlakes of NY. Owners on adjacent property to assist you in making your stay a memorable one.

13–20 Jun

$134 SGD per night

Superhost

Home in Whitney Point

4.83 out of 5 average rating, 132 reviews

River Cottage in Village high-speed internet

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!

15–22 Jul

$166 SGD per night

Guest favourite

Cabin in Lisle

4.94 out of 5 average rating, 251 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.

5–12 Oct

$252 SGD per night

Guest favourite

Home in Warren Center

5.0 out of 5 average rating, 148 reviews

Country Tucked Inn, with pond Sauna woods hunting.

Tucked Inn is a totally remodeled house in a quiet country setting. The pond offers swimming, a dock, pedal boat and fishing. The sunroom has a sauna for 2. The owners are next door and have a 500 acre family farm with beef cattle and a maple syrup operation. Sit on the front porch or grill on the back porch and enjoy the propane fire ring. Kids can run and play. Hunting available a mile away on a State Game Lands 219. Enjoy hiking in the large woods just out your back door.

2–9 Apr

$189 SGD per night

Guest favourite

Home in Newark Valley

4.95 out of 5 average rating, 250 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!

18–25 Dec

$138 SGD per night

Guest favourite

Cottage in Freeville

4.99 out of 5 average rating, 104 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.

10–17 Sep

$211 SGD per night