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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Two Bedroom Cottage Close To Town
Surrounded by mature trees, this single-story house offers a serene environment and a covered outdoor area.

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
Pet-friendly Cottage at Historic Millbrook Farm Estate
Stroll through the charming garden, surrounded by lush greenery and trees, to this traditional two-story house with a gabled roof.

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.4 out of 10, Exceptional, (8)
"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
Be in Nature at this Gorgeous Riverfront Cabin
Steps lead to a front door flanked by large windows, set amidst a beautifully manicured lawn and lush greenery.

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
Waterfall, Back Yard, Fire pit, and Grill!
Exterior

Waterfall, Back Yard, Fire pit, and Grill!

The price is HK$2,341
HK$3,483 total
includes taxes & fees
11 Aug - 12 Aug
Waterfall, Back Yard, Fire pit, and Grill!
Reset and Relax in Luxury Cottage
Guests can enjoy a serene forest view from this deck with a sturdy railing.

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.
Stylish single-story home with a gabled roof and inviting front porch.

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
Cozy cabin surrounded by trees, featuring a small porch with two chairs and a table.

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
Enjoy a serene outdoor space with a swimming pool, deck, and well-maintained lawn.

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!!"
18th Century Rosendale Cottage w/pool
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
The price is HK$3,061
HK$4,955 total
includes taxes & fees
9 Aug - 10 Aug
Magnificent Lake View
Luxe Family Home on Orange Lake w/ Private Dock!
Interior

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
Interior

Charming Gardiner Home w/ Yard & Sunroom

3.0 star property
10.0 out of 10, Exceptional, (1)
Charming Gardiner Home w/ Yard & Sunroom
Mountain View escape
Guests can enjoy a cabin-style retreat surrounded by a wooded area and a common deck.

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
Situated in a serene rural setting, this charming barn offers a peaceful retreat.

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
Pet-friendly Hopewell Junction Home w/ Pool
Enjoy a meal or relax on the deck with a table and six chairs, surrounded by a grassy area with trees.

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
Charming Victorian Retreat w/ Hudson River Views
Interior

Charming Victorian Retreat w/ Hudson River Views

3.0 star property
Charming Victorian Retreat w/ Hudson River Views
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Surrounded by lush greenery, this single-story house offers a serene and setting with a cozy porch and seating area.

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
Whimsical Woodland Cottage in Stone Ridge NY
Charming house with a front porch and barbecue grill, set amidst lush green surroundings.

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 HK$954
HK$2,721 total
includes taxes & fees
5 Aug - 6 Aug
Whimsical Woodland Cottage in Stone Ridge NY
Serene Holmes Cottage Near Lakes & Trails!
Front of property

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
Relax in a serene garden setting with Adirondack chairs surrounding a cozy fire pit.

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
Peaceful Hurley Retreat ~ 1 Mi to Main Street
Interior

Peaceful Hurley Retreat ~ 1 Mi to Main Street

3.0 star property
Peaceful Hurley Retreat ~ 1 Mi to Main Street
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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Top Pleasant Valley Hotel Reviews

Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

10/10 Excellent
"Great location. Nearby food options. Comfortable hotel. Friendly service"
Jane 1-night trip
Posted 1 day ago
Wingate by Wyndham Fishkill

Frequently asked questions

Why book your cottage in Pleasant Valley with Expedia?
Expedia has some great cottages in Pleasant Valley, so start packing for a memorable stay on nature's doorstep. If you're on a budget, choose how much you'd like to spend and your preferred property star rating. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the perfect fit whatever your getaway looks like.
How can I find cheap cottages in Pleasant Valley?
Expedia is here to help you track down cheap cottages in Pleasant Valley. To book a fantastic stay in just a few keystrokes, try out the filter tool to refine your search by budget, star rating and amenities.
What is there to do in Pleasant Valley near my cottage?
After you've settled into your hotel, venture out and discover the awesome things Pleasant Valley has on offer. Innisfree Garden is a great attraction to add to your itinerary.