Default HTG hotel image

Pleasantville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Pleasantville vacation rentals

A wooden door with a decorative knocker and a lantern above it.

1. Pleasant Grove Farm LLC

Pleasant Grove Farm LLC
3.0 star property
Lyons
9.4 out of 10, Exceptional, (105 reviews)
"This is our favorite place to stay every Labor Day weekend. It’s home away from home!"
United States
Craig
$140 nightly
The price is $157
Oct 19 - Oct 20
Total with taxes and fees
Pleasant Grove Farm LLC
A two-story brick house with a white front door, a small window, and a chimney.

2. Cozy and relaxing

Cozy and relaxing
Linton
9.6 out of 10, Exceptional, (13 reviews)
"The property was very clean and as advertised. We had a wonderful stay!"
United States
Jason L.
$206 nightly
The price is $231
Oct 25 - Oct 26
Total with taxes and fees
Cozy and relaxing
A wooden deck with a view of a lake and grassy fields.

3. Unique cozy 14x40 Cabin with a nice deck by the water .

Unique cozy 14x40 Cabin with a nice deck by the water .
Jasonville
9.8 out of 10, Exceptional, (33 reviews)
"Very clean and view was great and a very quiet place to relaxHost was fantastic "
United States
Glen C.
$174 nightly
The price is $195
Oct 19 - Oct 20
Total with taxes and fees
Unique cozy 14x40 Cabin with a nice deck by the water .
Private kitchen

4. Modern Tiny Home w/ Hot Tub Retreat

Modern Tiny Home w/ Hot Tub Retreat
Jasonville
9.6 out of 10, Exceptional, (18 reviews)
"Great little cozy place."
United States
DeWayne
$363 nightly
The price is $407
Oct 19 - Oct 20
Total with taxes and fees
Modern Tiny Home w/ Hot Tub Retreat
A room with two beds, a small table, a wooden sign on the wall, and a window with blinds.

5. Cozy 1-Bedroom Cabin Near Greene-Sullivan State Forest with AC

Cozy 1-Bedroom Cabin Near Greene-Sullivan State Forest with AC
Linton
$133 nightly
The price is $148
Oct 28 - Oct 29
Total with taxes and fees
Cozy 1-Bedroom Cabin Near Greene-Sullivan State Forest with AC
A covered outdoor area with a gravel path leading to a building with stone accents and a wooden pergola.

6. Modern Retreat w/ Private Hot Tub & Bunk Room

Modern Retreat w/ Private Hot Tub & Bunk Room
Jasonville
9.0 out of 10, Wonderful, (2 reviews)
"One of the best rentals we’ve been to! Highly recommend! Thanks so much for the cake, what a pleasant surprise!"
United States
Lisa P.
$584 nightly
The price is $654
Oct 19 - Oct 20
Total with taxes and fees
Modern Retreat w/ Private Hot Tub & Bunk Room
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pleasantville Hotel Reviews

Eagles Nest Camping Bee Hunter Cabin

Eagles Nest Camping Bee Hunter Cabin

10/10 Excellent
"Cozy little cabin! Perfect weekend getaway!"
Ashley M. 2-night trip
Posted 2 hours ago
Eagles Nest Camping Bee Hunter Cabin

Find out more about Pleasantville

Everything you need to know about Pleasantville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasantville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasantville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasantville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasantville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pleasantville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pleasantville rentals

At Expedia, we put the best Pleasantville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasantville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasantville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasantville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Pleasantville?

Yes, there are vacation rentals close to the most popular sights in Pleasantville, or you can choose a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Pleasantville?

Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio: Visitors like this Pleasantville vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What’s there to see and do in Pleasantville?

While you're exploring the area, Sullivan County Park and Shakamak State Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Elks Country Club and Sullivan City Park.

What’s a vacation rental in Pleasantville like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Pleasantville. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.