Photo by louann ohora

Book a Pleasant Valley Cottage

    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
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Pleasant Valley

Exterior
Mountain View escape
10.0 out of 10, Exceptional, (24)
"We've stayed in a number of VRBOs and none have been as well-appointed and welcoming as this Mountain View Escape home. Privacy and space, while close to wonderful towns and places to explore. Highly recommend!"
Mountain View escape
TV, fireplace, books
Dreamy Hudson Valley Cottage w/ State Park Views
10.0 out of 10, Exceptional, (2)
"This is a great cozy retreat. Clean. Everything you need, including firewood for the wood stove.Convenient to NY State Parks and not far from the Empire Trail and Hudson Valley Greenway so perfect for us to check off some of our NY State Parks Centennial Challenge tasks and get some hiking and biking in. It was perfect for the 2 of us. Ashley responded promptly to all of our communications and was a great host. Nice little touches like a basket of snacks added to the charm of this cozy cottage."
Dreamy Hudson Valley Cottage w/ State Park Views
Leggett Cottage, High Falls, NY.
10.0 out of 10, Exceptional, (62)
"The house is a well appointed one bedroom with a nicely done kitchen and kitchen equipment. The layout is comfortable and the host's art and the other art in the home makes it a fun place to stay. We enjoyed the stay and would gladly return!"
Leggett Cottage, High Falls, NY.
Save an average of 15% on thousands of hotels when you're signed in
Exterior
Private Guest Cottage @ The Sheeley House in High Falls NY.
10.0 out of 10, Exceptional, (1)
"Very beautiful surroundings. Manager Rob very helpful."
Private Guest Cottage @ The Sheeley House in High Falls NY.
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (6)
"This house was exactly as advertised and very charming. The owners were very easy to work with. We had a beautiful view of the lake from the porch. We would stay here again."
Candlewood Lake Retreat with year round views
Property grounds
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
10.0 out of 10, Exceptional, (2)
"We loved our weekend in Beacon. This small, charming rental was very clean and updated. The outdoor space made it feel bigger and you can’t beat the location. We highly recommend staying here and we woulld definitely come back!"
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
Exterior
Whimsical Woodland Cottage in Stone Ridge NY
10.0 out of 10, Exceptional, (6)
"My husband and adult son stayed here for a Hudson Valley holiday. This place is truly perfect for 2 people for a lovely getaway. Would have loved to be here in warmer weather to enjoy the front porch and firepit. It is decorated adorably. Best highlights: owner quick to respond, very comfy beds and cozy, warm gas fireplace. Just know that it is rustic cabin-like, so if you’re seeking more upscale then recommend other places. No shades except in the bedroom, no closet/dresser/place to hang or...
Whimsical Woodland Cottage in Stone Ridge NY
Interior
Country Cottage Retreat
10.0 out of 10, Exceptional, (9)
"we had a wonderful time! the cottage was very comfortable and really well-appointed. We made the most of the fireplace and our two dogs loved the access to the field and woods nearby. Susanne, the host, gave us great directions and was super friendly and helpful and we really appreciated the scones,chocolate and fresh local eggs left for us. We made the most of the easy access to the Rhinebeck restaurtants and hikes in the area and would love to come back! Thank you"
Country Cottage Retreat
Property grounds
Reset and Relax in Luxury Cottage
10.0 out of 10, Exceptional, (23)
"This is a nice place near the Omega Institute, tucked away with a nice woodsy walk in the neighborhood. The host cares about the quality of your stay. Nice, simple, clean, comfortable, everything you need. I will look to stay again in the future."
Reset and Relax in Luxury Cottage
View from property
Charming Cottage with Expansive Hudson River Views
10.0 out of 10, Exceptional, (7)
"Our stay couldn't have been better! We're two friends who were celebrating our birthdays and were here for a relaxing week of vacation. The cottage itself, the amenities, host, and location were all great. It's tucked away in a quiet neighborhood with lovely views of the river, five minutes away from Kingston (where we saw a concert at the Ulster Performing Arts Center, had a top-notch dinner at The Brickmen, and shopped at the vinyl stores). Maria was a perfect host and we loved seeing her son...
Charming Cottage with Expansive Hudson River Views
Smart TV, books
Be in Nature at this Gorgeous Riverfront Cabin
10.0 out of 10, Exceptional, (6)
"A great place to stay. Clean, stylish, and well appointed with great views and access to a small river. Highly recommend!!"
Be in Nature at this Gorgeous Riverfront Cabin
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
Fridge, microwave, oven, stovetop
Upstate Victorian Cottage in Quiet Village of Esopus
10.0 out of 10, Exceptional, (2)
"Very clean home. We were in the area for a family wedding and the location was great. We were totally satisfied with everything."
Upstate Victorian Cottage in Quiet Village of Esopus
Interior
The Schoolhouse, Rhinebeck Perfection
10.0 out of 10, Exceptional, (3)
"Beautiful, spacious, historic renovated schoolhouse, well appointed furnishings. Giant great room off the back and out to an expansive green which is NOT fenced enough to let your pet run loose, which they say in write up (our dog loved the great room to play in). A few things: If the weather is inclement, the firewood on the property along the fence will be wet. We arrived in rain and had sun the next two days but wood was wet, and could not locate any bagged firewood in Rhinebeck, so could not...
The Schoolhouse, Rhinebeck Perfection
Property grounds
Cozy Lakefront Cottage on Candlewood- Skiing, Hiking, Wineries, 90min from NYC
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the cottage. The location was ideal for visiting family and exploring the area. Sherman is super nice. And the house had everything we needed and charm to spare. It was winter, so we didn't make use of the lake, but when it snowed one morning, the scene was gorgeous. Thanks!"
Cozy Lakefront Cottage on Candlewood- Skiing, Hiking, Wineries, 90min from NYC
Sport court
Creekside Cottage The Fitz House Red Hook NY
10.0 out of 10, Exceptional, (1)
"The Fitz house is decorated like a fancy NYC apartment -- beautiful place. Location is close to lots in the Hudson Valley. My wife thought it would make a fabulous art studio. Would definitely consider coming back."
Creekside Cottage The Fitz House Red Hook NY
Terrace/patio
Writers Retreat/ Cozy Cottage w/ beautiful fire pit and backyard in Tillson, NY
10.0 out of 10, Exceptional, (2)
"The check in/out process was super-simple. The communication from the property manager was nice and cordial. The TV/couch area was a little cramped and the freeway noise was noticeable, but the bed mattress was one of the most comfortable mattresses that I have ever slept on. That bed was probably the highlight for me. We used the place as a sleeping spot as we traveled/explored the area and NYC."
Writers Retreat/ Cozy Cottage w/ beautiful fire pit and backyard in Tillson, NY
Exterior
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
9.8 out of 10, Exceptional, (45)
"The barn and surrounding area was very relaxing and so nice to be in the countryside. For us, visiting relatives just around the corner, it was absolutely perfect. "
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Lakefront cottage with Year round Hot Tub private beach and dock
9.6 out of 10, Exceptional, (73)
"Super fun weekend for us and our pup. Highly suggest this place for a weekend getaway with lake access"
Lakefront cottage with Year round Hot Tub private beach and dock
Don't see what you're looking for?
See all available properties in Pleasant 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.

Other property types in Pleasant Valley

Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
On the beach, sun-loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
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.