
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.

⭐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

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

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.

Quill Creek Aframe
Welcome to our charming A-frame retreat near Elk! At 101 Longacre Rd, Susquehanna, PA! This cozy cabin features 2 bedrooms, 1 bathroom, a spacious deck, back patio, and a fire pit. Perfect for couples, families, or friends, our cabin offers a serene escape with modern comforts. Enjoy the stunning surroundings, unwind by the fire, or explore the beauty of Susquehanna. Ideal for those seeking tranquility and adventure. Book your stay today and create lasting memories at our lovely A-frame cabin!

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.

Rink Side Cabin at The Farm Rink
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.

"Wilma" - Riverfront Cabin
This recently improved riverfront cabin, has a style all its own. Open entertainment space extends on to the 40 ft long deck. The many windows and doors allow nature in, complementing the locally sourced live edge countertops in the kitchen. Beautiful views are seen of the lush landscaping, river and distant mountain, from every room. The kitchen offers all ammenities, such as a dishwasher, large french door style refrigerator, and a ton of storage along with ample countertops.

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!

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!

Howland Farm
The John Howland Farm is an iconic 1840s family farm. We follow strict cleaning protocols and only accept whole house reservations. Your party will be the only guests at the farmhouse. The "Butterfly Suite" includes three bedrooms, sitting room with board games, books, and private bath. The "Garden Suite" is fully ADA accessible with bedroom, bath, and sitting room. The "Pine Cone Suite" is also ADA accessible with bedroom, bath, and adjacent laundry room.

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!

FLX 4-Lake View Wine Country Tiny Cabin
Nestled up on a hill with Seneca Lake peaking through the trees. 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!!
Popular amenities for Berkshire holiday rentals
Other great holiday rentals in Berkshire

Warner Big Blue House: Bdrm 2, Pet & Kid Friendly

Luxury townhouse near downtown!

The Night Owl /Room #1/ private and comfortable

Cricket's Farm, Bantam Room

Private Bedroom/bath in NY Southern Tier

Adventure Awaits A-Frame

Cozy Cabin in Candor

Peaceful Escape
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Boston Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Cornell University
- Watkins Glen State Park
- Greek Peak Mountain Resort
- Taughannock Falls State Park
- Chittenango Falls State Park
- Song Mountain Resort
- Watkins Glen International
- Chenango Valley State Park
- Cascadilla Gorge Trail
- Sciencenter
- Clark Reservation State Park
- Fox Run Vineyards
- Standing Stone Vineyards
- Bet the Farm Winery
- Six Mile Creek Vineyard




