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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

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

Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (34)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
Pet-friendly Cottage at Historic Millbrook Farm Estate
Interior

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
Interior

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
Exterior

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

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
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Exterior

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 FRONT COTTAGE - YEAR ROUND HOT TUB
Terrace/patio

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
Exterior

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!
Beach nearby, beach towels

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

9.4 out of 10, Exceptional, (91)
"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
Exterior

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 AED 705
AED 1,571 total
includes taxes & fees
10 Jun - 11 Jun
Whimsical Woodland Cottage in Stone Ridge NY
Magnificent Lake View
Miscellaneous

Magnificent Lake View

2.0 star property
Magnificent Lake View
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
Serene Holmes Cottage Near Lakes & Trails!
Interior

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
Terrace/patio

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
Leggett Cottage, High Falls, NY.

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

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

Charming Rhinebeck Cottage, 5 min. from town, King Bed!
Be in Nature at this Gorgeous Riverfront Cabin
Smart TV, books

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
Fridge, microwave, oven, stovetop

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
House (1 Bedroom) | Interior

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
Dreamy Hudson Valley Cottage w/ State Park Views
Interior

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.
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Frequently asked questions

Why book your cottage in Pleasant Valley with Expedia?
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