Photo by louann ohora

Search Cottages in Pleasant Valley

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 79 Cottages in Pleasant Valley with updated reviews, rates, and availability.

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

Pet-friendly Cottage at Historic Millbrook Farm Estate

10.0 out of 10, Exceptional, (1)
"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

Charming Cottage with Expansive Hudson River Views

10.0 out of 10, Exceptional, (14)
"Quaint, scenic, and quiet. A beautiful stay. "
Charming Cottage with Expansive Hudson River Views

Mountain View escape

10.0 out of 10, Exceptional, (54)
"This was such a lovely place to stay! Great location and beautiful setting. "
Mountain View escape

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

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

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

LAKE FRONT COTTAGE - YEAR ROUND HOT TUB

9.6 out of 10, Exceptional, (41)
"Great amenities, relaxing and extra touches were lovely"
LAKE FRONT COTTAGE - YEAR ROUND HOT TUB

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

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

9.4 out of 10, Exceptional, (90)
"Well appointed cabin was perfect for a quick weekend up to visit friends. Would love to come back in warm weather to take advantage of the proximity to the beautiful lake. Thanks!"
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

Whimsical Woodland Cottage in Stone Ridge NY

9.4 out of 10, Exceptional, (9)
"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 AEDĀ 705
AEDĀ 1,571 total
includes taxes & fees
10 Jun - 11 Jun
Whimsical Woodland Cottage in Stone Ridge NY

Charming Victorian Retreat w/ Hudson River Views

3.0 star property
Charming Victorian Retreat w/ Hudson River Views

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (72)
"Very comfortable, relaxing and clean. Great space. Will be back Thank you very much - Patricia"
Leggett Cottage, High Falls, NY.

Magnificent Lake View

2.0 star property
Magnificent Lake View

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

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (16)
"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

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (21)
"Wonderful time..beautiful location. "
Two Bedroom Cottage Close To Town

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

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

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

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
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.
Save an average of 15% on thousands of hotels when you're signed in

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.