
Places to stay in Pleasant Valley
Book unique places to stay, houses, and more on Airbnb
Top-rated places to stay in Pleasant Valley
Guests agree: these places to stay are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pleasant Valley places to stay
Other great vacation rentals in Pleasant Valley
Top guest favorite

Home in Millerton
4.97 out of 5 average rating, 181 reviewsVacation Home In Millerton
SarahRating, 5 stars1 week ago
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!
Top guest favorite

Home in Great Barrington
5 out of 5 average rating, 6 reviewsSummer & Leaf Season Rental!
AnnieRating, 5 stars3 months ago
What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!
Guest favorite

Home in Hunter Mountain, Hunter
4.96 out of 5 average rating, 104 reviewsPrivate Mountain Lodge, 10mins to Hunter & Windham
PaulRating, 5 stars2 months ago
My family's second visit to this beautiful gem overlooking the mountains and frozen pond. Our hosts are highly communicative and helpful. The description is accurate. Considering our 2nd visit and rebooked for 3rd in 2026 - this speaks volumes -- more than meets our needs, well stocked. We're looking forward to visiting during the summer months to further appreciate the views. Grateful to them for sharing their home with us.
Guest favorite

Guesthouse in Windham
4.97 out of 5 average rating, 100 reviewsLittle Bear’s Cottage Great location, cozy & cute
ChrisRating, 5 stars5 months ago
We had an amazing stay and we will come back 😊
Guest favorite

Home in Woodstock
4.92 out of 5 average rating, 468 reviewsMountain View Cottage - Sauna, Jacuzzi, Fire Place
SeanRating, 5 stars2 weeks ago
Unique space minutes form downtown Woodstock. The home offers peace and quiet to unwind from modern hectic life. Tune into focused intentional living. Records, wood fires, and sauna all help to create a retreat that’s sure to recharge and inspire. Lovely hosts!
Top guest favorite

Home in Greenwood Lake
5 out of 5 average rating, 119 reviewsEscape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC
TatyanaRating, 5 stars1 month ago
We had a staycation here and it was absolutely lovely. We enjoyed the space, especially the view. The hot tub was great in the chilly nights, played in the game room a bit, cooked in the kitchen and enjoyed some meals in the dining room. Easy to find, but felt very private. Thank you for sharing the lovely place.
Guest favorite

Cabin in Shandaken
4.99 out of 5 average rating, 104 reviewsA Place Called Home in The Catskill
KateRating, 5 stars1 month ago
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!
Superhost

Chalet in Fleischmanns
4.73 out of 5 average rating, 158 reviewsSauna equipped Belleayre Cozy Cabin
ChloeRating, 5 stars2 months ago
Perfect for a ski weekend. Sauna is great, and location cannot be beat.
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- Belleayre Mountain Ski Center
- Windham Mountain
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- Minnewaska State Park Preserve
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