Berkshire Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Berkshire vacation rentals

A log cabin interior with a wood-burning stove, a dining table, and a large window.

1. Round Top Retreat, Rustic Cabin

Round Top Retreat, Rustic Cabin
Richford
10.0 out of 10, Exceptional, (1 review)
"Great time!"
United States
Robert P.
The price is AED 364
AED 424 total
includes taxes & fees
15 Nov - 16 Nov
Round Top Retreat, Rustic Cabin
A living room with a patterned rug, wooden flooring, a dining table with chairs, a kitchen with wooden cabinets, a refrigerator, and a wall-mounted plant.

2. Charming 2-bedroom apartment in fabulous Willseyville with AC, WiFi

Charming 2-bedroom apartment in fabulous Willseyville with AC, WiFi
Willseyville
10.0 out of 10, Exceptional, (2 reviews)
"This two bedroom was comfortable, inviting, and well stocked. It was in a great location close to everything we needed. We will definitely be staying here again in the future. Highly recommend!!"
United States
Sherrie W.
The price is AED 334
AED 588 total
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom apartment in fabulous Willseyville with AC, WiFi
A rustic wooden cabin with a porch and a door, surrounded by lush greenery.

3. 600 Sq. ft Cabin with King Size Bed - Quiet Location, Close to Skiing

600 Sq. ft Cabin with King Size Bed - Quiet Location, Close to Skiing
Cortland
10.0 out of 10, Exceptional, (61 reviews)
"Impeccably clean, well stocked, beautiful area, perfect getaway. "
United States
Farhan I.
The price is AED 551
AED 710 total
includes taxes & fees
15 Nov - 16 Nov
600 Sq. ft Cabin with King Size Bed - Quiet Location, Close to Skiing
A wooden deck with a door and a utility box.

4. Cozy little house in Johnson City

Cozy little house in Johnson City
Johnson City
8.0 out of 10, Very good, (18 reviews)
"Second time staying here, everything was great!"
United States
Chad A.
The price is AED 298
AED 386 total
includes taxes & fees
16 Nov - 17 Nov
Cozy little house in Johnson City
A modern living room with a sofa, coffee table, and chairs. There is a dining area with a table and chairs. Large windows provide natural light and a view of the outdoors.

5. Charming 2BR condo at Greek Peak near Finger Lakes, Gutchess Sports complex

Charming 2BR condo at Greek Peak near Finger Lakes, Gutchess Sports complex
Cortland
9.8 out of 10, Exceptional, (15 reviews)
"Place was great. "
United States
Brian P.
The price is AED 661
AED 1,673 total
includes taxes & fees
19 Nov - 20 Nov
Charming 2BR condo at Greek Peak near Finger Lakes, Gutchess Sports complex
A compact living space with a sofa, a dining table, a kitchen area, and a bed with a sliding door.

6. BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY

BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
Greene
10.0 out of 10, Exceptional, (15 reviews)
"Property was beautiful would t change anything. Will definitely book again when we are in town."
United States
Lori
BRAND NEW! 1-bedroom apartment in the beautiful historic village of Greene, NY
A modern kitchen with stainless steel appliances, a dining area with a wooden table, and a balcony with a red railing and a yellow umbrella.

7. Family-Friendly Retreat near Cornell & Downtown

Family-Friendly Retreat near Cornell & Downtown
South Hill
9.6 out of 10, Exceptional, (18 reviews)
"Great family placeSuper comfortable and convenient to downtown"
United States
Karen W.
The price is AED 290
AED 1,258 total
includes taxes & fees
16 Nov - 17 Nov
Family-Friendly Retreat near Cornell & Downtown
A modern living room with a sofa, a small round table, a TV, and a sliding glass door leading to a patio.

8. Cozy Private Studio | Near Cornell & Downtown

Cozy Private Studio | Near Cornell & Downtown
South Hill
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 162
AED 537 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Private Studio | Near Cornell & Downtown
A modern kitchen with stainless steel appliances, dark cabinets, and a window providing natural light.

9. 1 Bedroom with a country view

1 Bedroom with a country view
Spencer
10.0 out of 10, Exceptional, (59 reviews)
"Quaint and inviting place to stay equipped with all the amenities."
United States
Sarah M.
The price is AED 413
AED 586 total
includes taxes & fees
15 Nov - 16 Nov
1 Bedroom with a country view
A wooden cabin interior with a dining table, chairs, a black refrigerator, wooden cabinets, and a window with blinds.

10. Mountain View Cabin - Best Night's Sleep at Greek Peak!

Mountain View Cabin - Best Night's Sleep at Greek Peak!
Cortland
9.6 out of 10, Exceptional, (14 reviews)
"The cabin was really great, super clean and cozy"
United States
Marissa W.
The price is AED 895
AED 1,725 total
includes taxes & fees
15 Nov - 16 Nov
Mountain View Cabin - Best Night's Sleep at Greek Peak!
A modern kitchen with white cabinets, a black microwave, a kettle, and a coffee maker.

11. Beautiful 2nd story apartment 10 minutes from 2 state parks.

Beautiful 2nd story apartment 10 minutes from 2 state parks.
Newfield
10.0 out of 10, Exceptional, (142 reviews)
"This was one of the best places we have stayed. Our hosts provided everything you could think of in the kitchen and the location was convenient to Ithaca and several state parks. If we are ever back in the area we would stay here in a heartbeat!"
United States
Dennis W.
The price is AED 433
AED 734 total
includes taxes & fees
15 Nov - 16 Nov
Beautiful 2nd story apartment 10 minutes from 2 state parks.
A lakeside cabin with a wooden deck and a stone pathway leading to the entrance.

12. Cozy 2-bedroom cabin in Vestal NY

Cozy 2-bedroom cabin in Vestal NY
Vestal
9.6 out of 10, Exceptional, (23 reviews)
"The view was amazing! Great location"
United States
Luke
The price is AED 496
AED 830 total
includes taxes & fees
7 Dec - 8 Dec
Cozy 2-bedroom cabin in Vestal NY
A porch with a wicker chair, a potted plant, and a door.

13. Spencer Village Colonial 2

Spencer Village Colonial 2
Spencer
10.0 out of 10, Exceptional, (14 reviews)
"Great stay!"
United States
Anand D.
The price is AED 547
AED 1,226 total
includes taxes & fees
15 Nov - 16 Nov
Spencer Village Colonial 2
A well-maintained lawn with a wooden deck, a small pond, and a clear view of the surrounding landscape.

14. *Newly renovated* guesthouse with beautiful views

*Newly renovated* guesthouse with beautiful views
Newfield
9.8 out of 10, Exceptional, (98 reviews)
"Perfect spot for a single or a couple with 2 pets (us). Nicely laid out. Only issue we had was the tough climb up the steps (in our late 60s though) and some sort of insects. (Not gross ones like roaches or anything like that) Would definitely stay again."
United States
Raymond
The price is AED 496
AED 834 total
includes taxes & fees
15 Nov - 16 Nov
*Newly renovated* guesthouse with beautiful views
A cozy cabin with wooden walls, a sofa, a desk with a computer, a refrigerator, and two windows.

15. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
9.8 out of 10, Exceptional, (22 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
The price is AED 413
AED 484 total
includes taxes & fees
15 Nov - 16 Nov
Fireside Cabin at Osborne Creek
A cozy living room with a wooden floor, a sofa, a coffee table, and a TV mounted on the wall.

16. Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly

Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
Greene
10.0 out of 10, Exceptional, (21 reviews)
"Cozy, clean and comfortable."
United States
Lyn J.
The price is AED 459
AED 535 total
includes taxes & fees
15 Nov - 16 Nov
Charming 1-bedroom apartment in Greene for up to 4 guests, family & dog friendly
A kitchen with dark wooden cabinets, a central island with bar stools, a microwave, and a refrigerator.

17. LOCATION, LOCATION, LOCATION!

LOCATION, LOCATION, LOCATION!
Cortland
9.8 out of 10, Exceptional, (6 reviews)
"Very cute place! Great stay overall!"
United States
Liz M.
The price is AED 738
AED 1,133 total
includes taxes & fees
15 Nov - 16 Nov
LOCATION, LOCATION, LOCATION!
A rustic cabin with a stone facade, a wooden balcony, and a stone entrance.

18. Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY

Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
Binghamton
9.8 out of 10, Exceptional, (145 reviews)
"A delightful weekend getaway.Kelly the owner went out of her way to make us comfortableAs soon as you walk in the front door you can smell the cleanliness and the essential oils.We loved the sunken jacuzzi, hot tub, multiple swings and all the twinkle lightsThe free continental breakfast was a bonus "
United States
Dawn N.
The price is AED 529
AED 1,220 total
includes taxes & fees
15 Nov - 16 Nov
Cozy/Chic Cabin ISOLATED RETREAT! Binghamton NY
A hotel lounge with orange patterned sofas, a flat-screen TV, a fireplace, and a small table with a vase of flowers.

19. 2 Full Beds | Non-Smoking, Mini Fridge

2 Full Beds | Non-Smoking, Mini Fridge
Binghamton
8.8 out of 10, Excellent, (3 reviews)
"A calm vibe filled the room with gentle heating that wasn't harsh or chilly, just right. Internet worked steadily during my visit without interruptions or slowdowns."
United States
Anonymous traveler
The price is AED 328
AED 371 total
includes taxes & fees
1 Dec - 2 Dec
2 Full Beds | Non-Smoking, Mini Fridge
A covered patio with a round glass table and four chairs, a beige umbrella, and a decorative lattice with flowers.

20. Your Home away from Home! Conveniently, centrally located, village home

Your Home away from Home! Conveniently, centrally located, village home
Homer
10.0 out of 10, Exceptional, (62 reviews)
"Cute apartment with everything we needed! Hosts provided everything we could think of! Would definitely rent again!"
United States
Ramona
The price is AED 422
AED 668 total
includes taxes & fees
11 Dec - 12 Dec
Your Home away from Home! Conveniently, centrally located, village home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

Top Berkshire Hotel Reviews

A wooden staircase leading to a balcony with bookshelves, a chair, and a table.
Yellow Barn Estate

Yellow Barn Estate

Yellow Barn Estate
Freeville

10/10 Excellent

We have stayed here often, and what we like most is that it's very homey, and we feel at home. It's a beautiful property, and the owners/hosts are always available if there are any issues. It's also very clean, and it has everything we need. We will continue to stay there!
United States
Vicky
Reviewed March 24, 2025
Yellow Barn Estate

Frequently Asked Questions

Can I find vacation rentals in Berkshire?

Yes, we give you a choice of vacation rentals near top points of interest in Berkshire, or you can go with a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Berkshire?

Tiny, A Frame, Loft Bed, LakeHouse: This vacation home rental outside of Berkshire is located on a lake and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Berkshire?

While exploring the area, visit family-friendly sights like Cascades Indoor Waterpark, or get outside and enjoy nature at Cornell Botanic Gardens. In the larger area, you’ll find Greek Peak Mountain Resort and Tompkins Cortland Community College.

What are vacation rentals like in Berkshire?

Vacation rentals are private accommodations you can book for a couple days or more in Berkshire. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.