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Featured Cottages in Pleasant Valley

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (23)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (91)
"Place was big enough for the two of us and a dog. Was very thankful the tiny home was dog friendly. Clean- location was good.Driveway was scary- to pull in and out. "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (18)
"Property was as advertised. Clean and nearby places we wanted to visit while, still being out of the way and quiet."
Be in Nature at this Gorgeous Riverfront Cabin

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.2 out of 10, Wonderful, (7)
"Stayed in this renovated farmhouse for a very snowy weekend. Nicely redone and furnished with spacious living/dining area. Could have fit 2 more adults or 2-3 kids. Hosts were lovely and introduced us to the goats. Too snowy and icy to get outdoors or explore much but local village has shops and kitchen was stocked with pantry staples and bottled water, milk/creamers for coffee so arrival day grocery run was not needed. Bonus large picture window let us enjoy the abundant snow from the warmth of...
Pet-friendly Cottage at Historic Millbrook Farm Estate

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (40)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (76)
"We really enjoyed our stay! The space was very nice & beautiful during the fall!"
Leggett Cottage, High Falls, NY.

Creekside Cottage The Fitz House Red Hook NY

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay. Communication with host was excellent. Highly recommend the location for a couple."
Creekside Cottage The Fitz House Red Hook NY

18th Century Rosendale Cottage w/pool

10.0 out of 10, Exceptional, (2)
"Beautiful place. The house had everything we couldve possibly needed. Can't wait to come back again!!"
The price is AU$1,284
includes taxes & fees
17 Aug - 18 Aug
18th Century Rosendale Cottage w/pool

Magnificent Lake View

2.0 star property
Magnificent Lake View

Whimsical Woodland Cottage in Stone Ridge NY

9.4 out of 10, Exceptional, (10)
"The whimsical cottage was very cute and comfortable. It was clean to the naked eye, however there were cobwebs in the windowsill behind the sofa. I wanted to go sit on the Adirondack chairs behind the house it those have not been wiped down at all. The shower is very small and dark. I realize it is an amenity to have its and pans however they definitely can be updated, it is hard to cook anything on an uneven pan. Overall it was a nice stay"
The price is AU$683
includes taxes & fees
29 July - 30 July
Whimsical Woodland Cottage in Stone Ridge NY

Mountain View escape

10.0 out of 10, Exceptional, (60)
"It’s adorable exactly What’s on the photos and equipped with everything you need for your stay definitely will be visiting it again. "
Mountain View escape

A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley

9.8 out of 10, Exceptional, (53)
"Very beautiful property! Beautiful night sky views and excellent nature, perfect place for a romantic weekend"
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property
Luxe Family Home on Orange Lake w/ Private Dock!

Charming Gardiner Home w/ Yard & Sunroom

3.0 star property
10.0 out of 10, Exceptional, (1)
Charming Gardiner Home w/ Yard & Sunroom

Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia

10.0 out of 10, Exceptional, (1)
"This was the perfect size cottage for 5 of us, with two rooms with queen size beds and one small room with a twin. The setting was very pretty, and the salt water heated pool was a good size and my grandchildren enjoyed swimming in it. We were within walking distance of the small town, and I would recommend staying there."
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia

Charming Victorian Retreat w/ Hudson River Views

3.0 star property
Charming Victorian Retreat w/ Hudson River Views

Serene Holmes Cottage Near Lakes & Trails!

3.0 star property
Serene Holmes Cottage Near Lakes & Trails!

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

10.0 out of 10, Exceptional, (7)
"Loved staying at this spot when dropping our daughter off for school!"
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

Fire Pit + On-site Pond: Hudson Valley Home!

3.0 star property
Fire Pit + On-site Pond: Hudson Valley Home!

Pet-friendly Hopewell Junction Home w/ Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was so incredible. Not only was it in a quiet nice neighborhood the inside was incredible too. Pool table as well as a pool it was perfect for my stay to have fun and enjoy our time. They were very communicative and welcoming to their house. Everything was comfortable and clean. Can’t say any bad things about this place. Definitely going to book again. I already miss it. "
Pet-friendly Hopewell Junction Home w/ Pool
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.
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Frequently asked questions

What is there to do in Pleasant Valley near my cottage?
There are loads of wonderful things that'll fill up your itinerary in Pleasant Valley. Head for renowned attractions like Chance Theatre, Hyde Park Historical Society Museum and James Baird State Park. Clinton Vineyards, Franny Reese State Park and Mid-Hudson Childrens Museum also appeal to many visitors.