Search Pleasantville Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 38 Cottages in Pleasantville with updated reviews, rates, and availability.

Fridge, microwave, stovetop, coffee/tea maker
Putnam Valley Vacation Rental: Patio & Lake Views!
9.8 out of 10, Exceptional, (7)
"Nuery was attentive and wonderful! Thank you for your thoughtful flowers. The listing could have been more descriptive regarding the separation between the large bedroom and full bath from the rest of the house. Too many air fresheners! The kitchen is dark, needs brighter light bulbs. Those are my suggestions. Otherwise the house is gorgeous and it was a great place to stay!"
Putnam Valley Vacation Rental: Patio & Lake Views!
Interior
Lovely Home Near FDU & Holy Name Hospital!
3.0 star property
8.0 out of 10, Very Good, (1)
Lovely Home Near FDU & Holy Name Hospital!
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is $184
$264 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Smart TV, computer monitors, printers
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
10.0 out of 10, Exceptional, (2)
"John was a fantastic host - his home was the perfect solution for us for a few days while we were in the process of moving to the area and our home wasn't ready yet. Great communication with us prior to check-in, very responsive to our questions and needs at the beginning and throughout our stay. Home is as pictured in the photos with very nice touches throughout. Washer/dryer and dishwasher in great working condition. Location super close to Scotts Corners where there are nice local...
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Fridge, microwave, oven, stovetop
Cozy Rustic Getaway w/ HBO, Porch & Grill Near Lake
9.8 out of 10, Exceptional, (10)
"This property is a serene location in the Hudson Highlands that has convenience and good proximity to stores & multiple communities in the area. This home had everything we were looking for and was very comfortable for us. Our host was great too!"
Cozy Rustic Getaway w/ HBO, Porch & Grill Near Lake
Smart TV, fireplace
Beautiful Cottage in Hudson Valley w/Pool & Views
9.8 out of 10, Exceptional, (8)
"This house is amazing! Has practically every amenity you'd need. Gorgeous, clean, comfortable, and very inviting. Check-in was a breeze. I can't wait to come back!"
The price is $300
$698 total
includes taxes & fees
Jun 2 - Jun 3
Beautiful Cottage in Hudson Valley w/Pool & Views
Fridge, microwave, oven, stovetop
Beach house cottage steps to private beach in the heart of Bayville
10.0 out of 10, Exceptional, (2)
"Comfortable, immaculate, well supplied, wonderful location…close to family members in Bayville. Plenty of delicious nearby restaurants and markets. Lots of historical sites in area. Overall a great positive experience. And the bunny is a wonderful extra!"
Beach house cottage steps to private beach in the heart of Bayville
Fridge, microwave, oven, stovetop
Second floor cottage apartment located in a private community.
10.0 out of 10, Exceptional, (11)
"This was a great property - location was perfect and the hosts were so easy to communicate with. It was exactly as pictured and was a great stay!"
Second floor cottage apartment located in a private community.
Pool
Adirondacks in Westchester
10.0 out of 10, Exceptional, (1)
"This location is gorgeous! I could just sit on the porch all day and look out at the trees, stream, and lake. It was a perfect get away from 2 days."
Adirondacks in Westchester
Interior
South Salem Vacation Rental w/ Furnished Deck!
10.0 out of 10, Exceptional, (1)
"Everything was easy and fine at the space. I had to stay for family reasons - so "location" was the most important factor to me. The worst thing in the unit is that the spiral stair is narrow - and a fat person or person with bad knees is NOT going to be using that stairwell easily. Otherwise, the unit had everything I needed and was perfectly appointed for an easy weekend stay. Enjoy!"
South Salem Vacation Rental w/ Furnished Deck!
Interior
Charming Mamaroneck Home ~ 22 Mi to Manhattan
3.0 star property
6.0 out of 10, (1)
"Great quiet neighborhood, but this is only part of the home (1st floor, basement, and part of the 2nd floor) and the people upstairs are stepping loudly late into the night. The 3rd bathroom is in the basement with no shower curtain and a shower head that must be held during your entire shower. It was the 1 room that was actually dirty and I cleaned it before we used it. Internet info was inaccurate but provided when we requested. TV instructions lacking. Plenty of room for hanging out and...
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Interior
Putnam Valley Vacation Rental: Patio & Lake Views!
3.0 star property
Putnam Valley Vacation Rental: Patio & Lake Views!
Interior
Updated Home w/ Patio Half Mile to West Point
3.0 star property
Updated Home w/ Patio Half Mile to West Point
Living area
Trendy 1 bedroom +loft apartment w/ parking
10.0 out of 10, Exceptional, (1)
"My husband and I are relocating to the East Coast and after a week-long drive across the country, we were happy, tired and grateful to arrive at Leti’s lovely apartment for a 3-week stay. It was exactly what we had hoped for —in fact, better than expected. The unit had parking, a fenced yard (with patio table and grassy area), a washer-dryer (with soap provided!) and a wonderful, well-appointed full kitchen and living space. The apartment was extremely clean with new furnishings and...
Trendy 1 bedroom +loft apartment w/ parking
Exterior
California cozy cottage/studio in the middle of the Greenwich
10.0 out of 10, Exceptional, (1)
"This VRBO was a pleasure! Host Olga was very accommodating. This was my first VRBO experience and I will definitely do this again. So much nicer than a hotel stay. It was a wonderful 5 days! I would highly recommend Olga and her California Cottage. "
California cozy cottage/studio in the middle of the Greenwich
Interior
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
3.0 star property
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Interior
Briarcliff Manor Estate w/ Hudson River Views
3.5 star property
Briarcliff Manor Estate w/ Hudson River Views
Interior
Lakefront New York Abode w/ Deck, Grill & Fire Pit
3.0 star property
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Interior
Glen Cove Home: Walk to Boardwalk + Dining!
3.5 star property
Glen Cove Home: Walk to Boardwalk + Dining!
Fridge, microwave, stovetop, coffee/tea maker
Ridgefield Cottage: Walk to Town & Movie Theater!
Ridgefield Cottage: Walk to Town & Movie Theater!
Don't see what you're looking for?
See all available properties in Pleasantville
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 Pleasantville

Exterior
Stamford Suites
2.5 star property
7.0 out of 10, Good, (710)
"Not a bad stay overall. Nice location opposite the police headquarters and courthouse. Friendly staff. Brianna the hostess was very nice. The suite was very large. The only thing is that the carpet needs changing. The continental breakfast wasn't appetizing but there's food all around the area. But all in all it was an enjoyable stay."
The price is $169
$195 total
includes taxes & fees
May 30 - May 31
Stamford Suites
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (49)
"Beautiful location and old, well-maintained house. Really perfect for our family group of 17"
Waterfront Retreat Center for Health & Wellness
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is $184
$264 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.

Pleasantville Cottages information

Number of reviews
123
Accommodation
38 Cottages
Lowest Price
$184
Highest Price
$300

Frequently asked questions

Why book your cottage in Pleasantville with Expedia?
Expedia has some excellent cottages in Pleasantville, so start planning for an unforgettable vacay on nature’s doorstep. If you’re on a budget, select how much you want to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with a pool or free WiFi. We’ll help you find the perfect pad whatever your bank balance or plans.
How can I find cheap cottages in Pleasantville?
A wonderful way to score cheap cottages in Pleasantville is with Expedia’s user-friendly filter tool. Narrow down your search results by star rating, budget and amenities to take advantage of unbeatable prices in just a few clicks.

Recent reviews of Pleasantville hotels
Expedia verified reviews

Radio Hotel

Radio Hotel

5/5 Excellent
"Good "
A verified traveler from St thomas stayed at Radio Hotel
Posted 1 day ago
Radio Hotel