Berkshire vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Berkshire

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

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Guest favorite

Guesthouse in Ithaca

4.97 out of 5 average rating, 700 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.

Jan 6 – 13

G$26,946 GYD per night

Guest favorite

Home in Newfield

4.98 out of 5 average rating, 127 reviews

Camp S’mores- An A-Frame for the modern traveler

Welcome to Camp S’mores- this revitalized luxury A-frame has all the modern amenities you need for your Finger Lakes adventure. We just brought new life into this house from top to bottom. The home features three bedrooms and a Murphy bed in the game room on the lower level. EV charger. It wouldn't be camp without a pool so our home has a large HEATED in-ground pool is open May 15th - Oct 1st. The house is located outside of town on 2+ private acres. Dog friendly, sorry no cats or other pets

Feb 13 – 20

G$145,829 GYD per night

Guest favorite

Cabin in Brooktondale

4.95 out of 5 average rating, 139 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

Apr 21 – 26

G$40,159 GYD per night

Guest favorite

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!

Oct 30 – Nov 6

G$30,596 GYD per night

Guest favorite

Home in Spencer

4.96 out of 5 average rating, 178 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.

Sep 20 – 27

G$20,469 GYD per night

Superhost

Home in Whitney Point

4.84 out of 5 average rating, 131 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!

Jul 11 – 18

G$25,455 GYD per night

Guest favorite

Cabin in Lisle

4.94 out of 5 average rating, 250 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.

Oct 1 – 8

G$38,632 GYD per night

Guest favorite

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.

Mar 24 – 31

G$29,511 GYD per night

Guest favorite

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!

Dec 25 – Jan 1

G$21,105 GYD per night

Guest favorite

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.

Aug 6 – 13

G$33,965 GYD per night

Guest favorite

Cottage in Candor

4.97 out of 5 average rating, 244 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!

Jun 27 – Jul 4

G$25,517 GYD per night

Guest favorite

Cottage in Tully

4.91 out of 5 average rating, 266 reviews

Lakeside Cottage

Spend a relaxing visit lakeside in our rustic little cottage on beautiful Song Lake. Our quaint little two bedroom cabin comes with all the comforts of home. Enjoy swimming, kayaking, fishing, or just relaxing lakeside. Also great for skiing in the winter, with Song Mountain less than a mile away, and 2 other ski resorts nearby. Just off interstate 81 and a short drive to Syracuse, the Finger Lakes or Ithaca.

Nov 3 – 10

G$23,303 GYD per night