Photo by louann ohora

Search Cottages in Pleasant Valley

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 65 Cottages in Pleasant Valley with updated reviews, rates, and availability.

Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (46)
"Can’t wait to go back, if I could move this home to Myrtle Beach I would. Fantastic communication with homeowner, great location. Homeowner keeps the home stocked with goodies, extra plus! Very cozy and Quiet it’s a 10 Star "
Mountain View escape
Two Bedroom Cottage Close To Town
Exterior

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
Be in Nature at this Gorgeous Riverfront Cabin
Wappinger Cottage on a Summer Evening

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (14)
"Beautiful house. Really enjoyed the views even. Can only imagine what it round be like in the summer. The host always answered if I had questions and was informative with process. It was a great stay. Thank you!!!"
Be in Nature at this Gorgeous Riverfront Cabin
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Hand-hewn beams & cathedral ceilings

A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley

9.8 out of 10, Exceptional, (52)
"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
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

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

9.4 out of 10, Exceptional, (87)
"The parking situation was a bit tricky because there was no good way to back in. Other than that, location was great - cute area! "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Reset and Relax in Luxury Cottage
Interior

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (32)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
Whimsical Woodland Cottage in Stone Ridge NY
Curl up on this plush, gorgeous leather couch next to a picture perfect fire.

Whimsical Woodland Cottage in Stone Ridge NY

9.8 out of 10, Exceptional, (8)
"Whimsical cottage was just as described. The owner was very responsive with any questions. The location was perfect for our needs. It is definitely meant for a couples weekend away, but was sufficient for the three of us."
The price is AED 496
AED 1,200 total
includes taxes & fees
18 Feb - 19 Feb
Whimsical Woodland Cottage in Stone Ridge NY
Leggett Cottage, High Falls, NY.

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (70)
"Again everything was perfect. Love staying at this location. Perfect Perfect especially for me. Again Thank You and Happy New Year. Hope to be back very soon - Patricia"
Leggett Cottage, High Falls, NY.
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Private Dock

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
Dreamy Hudson Valley Cottage w/ State Park Views
Garrison Vacation Rental | 1BR | 1BA | 650 Sq Ft | Steps Required

Dreamy Hudson Valley Cottage w/ State Park Views

9.8 out of 10, Exceptional, (12)
"We loved our two nights at this perfect, comfortable cottage in the Garrison woods. Communication with Ashley was terrific, very prompt and welcoming. The house was very clean and we had a great view. Thank you for a great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Goose Landing Cottage by the lake with BRAND NEW year-round Hot Tub
Living area

Goose Landing Cottage by the lake with BRAND NEW year-round Hot Tub

9.4 out of 10, Exceptional, (35)
"This was our second time staying at Goose Landing, and it remains the perfect weekend spot. As we have a kid attending nearby Bard College, I anticipate that we will be making many more such trips. "
Goose Landing Cottage by the lake with BRAND NEW year-round Hot Tub
Charming Rhinebeck Cottage, 5 min. from town, King Bed!
Exterior

Charming Rhinebeck Cottage, 5 min. from town, King Bed!

Charming Rhinebeck Cottage, 5 min. from town, King Bed!
LAKE FRONT COTTAGE - YEAR ROUND HOT TUB
Private Hot Tub overlooking Lake

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
Charming Cottage with Expansive Hudson River Views
Swan cottage is perched on a hill with gorgeous river views.

Charming Cottage with Expansive Hudson River Views

10.0 out of 10, Exceptional, (13)
"Lovely"
Charming Cottage with Expansive Hudson River Views
Schoolhouse No. 11 Newly RENOVATED Upstate Hudson Valley - Catskill Getaway
Exterior

Schoolhouse No. 11 Newly RENOVATED Upstate Hudson Valley - Catskill Getaway

10.0 out of 10, Exceptional, (1)
"My husband and I spent a few days at Steven’s beautifully decorated historic schoolhouse with our pup, and had a wonderful time, despite the heatwave! Steven is an incredibly responsive host and had a binder full of helpful recommendations for hiking and local food. We will be back!"
Schoolhouse No. 11 Newly RENOVATED Upstate Hudson Valley - Catskill Getaway
Hilltop House: Charming 1980's Kingston Farmhouse
Welcome to Hilltop House!

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
15% off; private pond; fireplace; 4-min to village
Living room with working fireplace. Relax with friends by a nice fire.

15% off; private pond; fireplace; 4-min to village

9.0 out of 10, Wonderful, (4)
"I was looking to get our adult children and their significant others together for the week without worrying about hotels, trains, or ride sharing. Everyone came out to the house secluded from the big city and it was great. The house was a good size for 6 of us and located near cute little towns of Rhinebeck and Kingston which both offered shopping walking and food. The property was well located in the woods with a cute pond on property. We’re city folks so the fire pit and woods walking was...
15% off; private pond; fireplace; 4-min to village
Kingston Home < 2 Mi to Bluestone Wild Forest
Living area

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
Hudson Valley Horse Farm Retreat in Salt Point
Exterior

Hudson Valley Horse Farm Retreat in Salt Point

3.0 star property
8.0 out of 10, Very Good, (1)
Hudson Valley Horse Farm Retreat in Salt Point
Esopus Creek Cottage

Esopus Creek Cottage

Esopus Creek Cottage
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.
Don't see what you're looking for?
See all available properties in Pleasant Valley
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pleasant Valley

Hamptons on the Hudson in South Saugerties
Pool

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
Hamptons on the Hudson in South Saugerties
The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (65)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
Spacious New Luxurious holiday house in lovely Hudson Valley
Living area

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
The price is AED 2,002
AED 2,997 total
includes taxes & fees
1 Mar - 2 Mar
Spacious New Luxurious holiday house in lovely Hudson Valley
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.

Frequently asked questions

Why book your cottage in Pleasant Valley with Expedia?
Reserving a cottage in Pleasant Valley is as simple as deciding on your travel dates and choosing an ideal place for a getaway in the outdoors. From chic retreats to low-cost properties and cottages that feature perks like a pool, Expedia has something for all styles. As for awesome deals? We’ve got them as well!
How can I find cheap cottages in Pleasant Valley?
Expedia can help you track down cheap cottages in Pleasant Valley. To lock in your dream stay in a few clicks, simply use our convenient filter tool to refine your search results by amenities, star rating and budget.