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Featured Cottages in Pleasant Valley

Mountain View escape

10.0 out of 10, Exceptional, (43)
"Charming. Peaceful. Beautiful. Well-designed. Well-stocked. I cannot recommend this place enough. It is the ideal getaway for an individual or couple. Hope to have a reason to return soon! "
Mountain View escape

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (31)
"Beautiful place about a 15 minute drive out of Rhinebeck. Great views, well equipped kitchen and spacious living quarters. Bed is a king and super comfy. The hosts were so kind and accommodating with lots of great suggestions for what to do and where to eat. You’ll love it!"
Reset and Relax in Luxury Cottage

Dreamy Hudson Valley Cottage w/ State Park Views

9.8 out of 10, Exceptional, (11)
"Absolutely gorgeous house! Great location and a beautiful view from the porch. Would highly recommend to anyone. "
Dreamy Hudson Valley Cottage w/ State Park Views

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

9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

Candlewood Lake Retreat with year round views

10.0 out of 10, Exceptional, (10)
"Liked outdoor area and fire place "
Candlewood Lake Retreat with year round views

LAKE FRONT COTTAGE - YEAR ROUND HOT TUB

9.4 out of 10, Exceptional, (40)
"came here with my partner to celebrate my birthday. it was the perfect place to relax & wind down from living in the city. i would love to come back during warmer months!"
LAKE FRONT COTTAGE - YEAR ROUND HOT TUB

Whimsical Woodland Cottage in Stone Ridge NY

9.8 out of 10, Exceptional, (7)
"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"
Whimsical Woodland Cottage in Stone Ridge NY

Country Cottage Retreat, Fido stays for free

10.0 out of 10, Exceptional, (12)
"perfect in every way. Friendly host couldn't be more helpful. With all the hiking one could hope for right out the door, our dog had a a great time too.We look forward to a return visit soon."
Country Cottage Retreat, Fido stays for free

Two Bedroom Cottage Close To Town

9.4 out of 10, Exceptional, (19)
"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

Charming Cottage with Expansive Hudson River Views

10.0 out of 10, Exceptional, (11)
"It was a wonderful and magical place. The interior design was lovely - so clean and luxurious. The beds were very very comfortable and the owner was very easily accessible at all times."
Charming Cottage with Expansive Hudson River Views

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (66)
"Lovely property in great location. Easy to explore Catskills and Hudson Valley. Amenities close by. "
Leggett Cottage, High Falls, NY.

Hilltop House: Charming 1980's Kingston Farmhouse

9.8 out of 10, Exceptional, (11)
"I love old homes and their quirky aspects like squeaky floors and doors also the peaceful surroundings. The house was very convenient to Kingston and amenities. Loved the house and neighborhood, I would definitely stay there again!"
Hilltop House: Charming 1980's Kingston Farmhouse

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (12)
"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

Dreamy Hudson Valley Cottage w/ State Park Views

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views

Esopus Creek Cottage

Esopus Creek Cottage

The Schoolhouse, Rhinebeck Perfection

10.0 out of 10, Exceptional, (5)
"Our second stay at the Schoolhouse. Perfect layout and setup for us. Light and airy greatroom, Bedrooms on opposite sides of the house offer privacy for us and our guest. As the weather gets cooler, would be nice to have a working fireplace, otherwise a terrific stay. Pictures on the website do it justice. A little off the beaten path, but only 5 minutes to town. We'll be back next year!"
The price is AU$811
includes taxes & fees
10 Dec - 11 Dec
The Schoolhouse, Rhinebeck Perfection

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

10.0 out of 10, Exceptional, (5)
"Lovely little cottage right on the arm of the lake. Nicely appointed and updated, quiet and great for a couple. Nearby towns are adorable."
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

Kingston Home < 2 Mi to Bluestone Wild Forest

3.0 star property
6.0 out of 10, (1)
"No lighted house numbers, so an evening check in was difficult. Attempted to get more blankets, and our texts were unanswered for a 3 night stay. "
Kingston Home < 2 Mi to Bluestone Wild Forest

Modern Hudson Valley Creekside Retreat + Hot Tub!

10.0 out of 10, Exceptional, (9)
"The house is hosted by someone who is very thoughtful. Every detail that a guest may need was considered. For example, there were small toiletries like toothpaste there. The entire place was immaculate and totally renovated. The kitchen had everything. Well stocked with all the appliances and tools you might need. Its 15 min from Rhinebeck. Very convenient location. We highly recommend. "
Modern Hudson Valley Creekside Retreat + Hot Tub!

Creekside Cottage The Fitz House Red Hook NY

10.0 out of 10, Exceptional, (3)
"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
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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Other property types in Pleasant Valley

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

9.2 out of 10, Wonderful, (35)
"I loved the location surrounded by mostly woods and the quiet atmosphere. The hosts are very nice and were very helpful. Everything I needed was inside. I may be back!"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (74)
"The house is as advertised. Good amount of room. The host was pretty communicative. No complaints from the property. Just wish they had a bigger table for group dinners"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (11)
"This was a extended work visit, and the property was perfect for us and the host was very accommodating whenever needed. I can see a wedding, reunion or a quiet getaway for a large family at this location."
The Scenic Mansion With Breathtaking View
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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.