
Berkshire vacation rentals
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Top-rated vacation rentals in Berkshire
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Berkshire vacation rentals
Other great vacation rentals in Berkshire
Guest favorite

Cottage in Smyrna
4.96 out of 5 average rating, 69 reviewsHidden LakeFront Retreat
CourtneyRating, 5 stars1 month ago
The house was perfect! Seems to be an all season location. Fantastic access to Hamilton and Colgate. Also great location for discovering restaurants and activities beyond Hamilton. Can’t wait to visit again!
Guest favorite

Townhouse in Cortland
4.96 out of 5 average rating, 113 reviewsPerfect for a quick getaway. Sleeps 10.
AnnaRating, 5 stars2 weeks ago
House is located in a quiet area with beautiful views & parking for 2 cars or more if you need it. Kitchen is well equipped. 2 bathrooms is so great for a bigger group of ppl. Washer & dryer always comes handy. There’s planty of towels & linens in case you need extras . There’s a cozy fireplace ( we didn’t use it since weather was in 70’s) Great place for a longer stay. Ours was short & not enough time to enjoy the views & area.
Guest favorite

Farm stay in Meshoppen
4.93 out of 5 average rating, 147 reviewsCozy country farmhouse with HOT TUB!!
DORARating, 5 stars2 weeks ago
Overall, we really enjoyed our stay! The house was as described. Alicia was super responsive and easily available to answer our questions. The house was spacious, cozy, and it was clean, although there were areas that weren't exceptionally clean, it didn't bother us. steep stairs, were a bit of concern as we had a senior relative in our party. It was a beautiful area, sadly we weren't able to take full advantage of all the amenities, as we were in Binghamton for graduation ceremonies—which was quite a drive —so we only got to enjoy the house a little. Definitely a nice place to enjoy being together as family to celebrate a major milestone in our lives. Thanks Alicia and Lenny!
Guest favorite

Home in Sayre
4.96 out of 5 average rating, 181 reviewsBeemans home on the hill.
WilliamRating, 5 stars4 days ago
We loved this place! Our family (6 of us) were in town for a family wedding. The house was perfect. Room for all of us, beautiful house. large and spacious, big bedrooms with comfortable bed, fully equipped kitchen (with plenty of coffee). Everything was clean and pristine. The house is very remote in a beautiful spot. We could not have asked for more.
Guest favorite

Tiny home in Burdett
4.91 out of 5 average rating, 246 reviewsVineyard Villa C
ShannonRating, 5 stars3 months ago
We loved our stay at Enrico’s tiny home! It was the perfect size for us with great views! The area had lots to do, even during the winter (technically off season). The place was very cozy, perfectly clean, and inviting. Thanks again!
Guest favorite

Cottage in Penn Yan
4.91 out of 5 average rating, 134 reviewsHeart of the Fingerlakes Wine Country
ChristaRating, 5 stars6 months ago
Thank you for letting us stay at your lovely house! We had the best time. The location is perfect, the house was so clean and the view was stunning. We highly recommend this lovely lake house!
Top guest favorite

Home in Unadilla
5 out of 5 average rating, 32 reviewsEscape the City
J LRating, 5 stars1 week ago
The home was very comfortable and good for large groups. We were in town for the General Clinton Canoe Regatta. There were multiple seating areas and nooks to hang out in so everyone could have their own space or gather for a big family meal. Garden space and fire pit lovely and well maintained. We had rain, so the covered porch was much appreciated! Comfortable beds. Hot tub. Kitchen large enough for prepping big meals and well equipped. Driveway fit all 6 of our cars without issue. Thoughtful touches like plenty of coffee, ice packs in freezer, plenty of easy to find cleaning supplies and laundry room, and local recommendations. Super responsive host and very accommodating. All in all a really great house.
Top guest favorite

Home in Burdett
4.97 out of 5 average rating, 416 reviewsBurdett Home with a View. Perfect location.
NancyRating, 5 stars1 week ago
I had an amazing stay at this property. One of the highlights was the sunsets. Every evening felt like a private show, with breathtaking views that made it hard to put the camera down. The space itself was spotless and well-equipped with everything I needed. You can tell the host put a lot of care into making sure guests feel at home. If you are looking for a comfortable,convenient, and scenic getaway, this place checks all the boxes. I would absolutely stay here again!
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