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Pleasantville Vacation Rentals

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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
The price is ￥22,123
￥24,778 total
includes taxes & fees
Oct 19 - Oct 20
Pleasant Grove Farm LLC
A wooden door with a window, a white shelf with jars and lanterns, and a white wall with a light switch.

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.
The price is ￥20,906
￥36,512 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is ￥16,497
￥30,866 total
includes taxes & fees
Oct 19 - Oct 20
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
The price is ￥40,847
￥64,330 total
includes taxes & fees
Oct 19 - Oct 20
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
The price is ￥17,777
￥23,451 total
includes taxes & fees
Oct 28 - Oct 29
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.
The price is ￥59,569
￥103,352 total
includes taxes & fees
Oct 19 - Oct 20
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.
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Top Pleasantville Hotel Reviews

Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio

Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio

10/10 Excellent
"Very nice property."
Darius 2-night trip
Posted 3 days ago
Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio

Find out more about Pleasantville

Search for holiday rentals in Pleasantville on Expedia! You can easily find your home rentals, villas, holiday apartments in Pleasantville using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pleasantville!

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.