Pleasantville Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Pleasantville

Peaceful Cabin By The Lake
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Peaceful Cabin By The Lake

9.0 out of 10, Wonderful, (14)
"Quiet area and nice spot for campfire and BBQ"
Peaceful Cabin By The Lake
Lake View Cabin
Exterior

Lake View Cabin

9.8 out of 10, Exceptional, (79)
"As always, David and Sandy were great hosts and continued to improve on an already great cabin. Fishing was plentiful as was the wildlife. We always enjoy staying here, no neighbors, no noise and complete privacy. We are looking forward to year 6!"
Lake View Cabin
Cozy cottage 4 minutes from Lake Sullivan!
Dining

Cozy cottage 4 minutes from Lake Sullivan!

10.0 out of 10, Exceptional, (15)
"Great place to stay, clean and comfortable "
Cozy cottage 4 minutes from Lake Sullivan!
Pleasant Grove Farm LLC
Cottage, Ensuite (Quail Run Cottage) | Exterior

Pleasant Grove Farm LLC

3.0 star property
9.4 out of 10, Exceptional, (99)
"This is our favorite place to stay every Labor Day weekend. It’s home away from home!"
$130 nightly
The price is $146
Sep 7 - Sep 8
Total with taxes and fees
Pleasant Grove Farm LLC
Unique cozy 14x40 Cabin with a nice deck by the water .
Interior

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

9.8 out of 10, Exceptional, (15)
"Wonderful weekend, beautiful lake. Loved our stay!"
$174 nightly
The price is $195
Sep 4 - Sep 5
Total with taxes and fees
Unique cozy 14x40 Cabin with a nice deck by the water .
Hillenbrand Hideaway
Terrace/patio

Hillenbrand Hideaway

8.0 out of 10, Very Good, (3)
"Loved this!! It was super cute and cozy!! "
Hillenbrand Hideaway
Quiet Country Cabin • Near Trails & State Parks
Dining

Quiet Country Cabin • Near Trails & State Parks

Quiet Country Cabin • Near Trails & State Parks
Private, cozy cabin on 13 acres with two ponds
Smart TV, fireplace, DVD player, video library

Private, cozy cabin on 13 acres with two ponds

10.0 out of 10, Exceptional, (43)
"Spacious clean cabin with every amenity a family would need. We enjoyed our stay."
Private, cozy cabin on 13 acres with two ponds
Beach Comber Lake Side canvas Cottage Tent
Exterior

Beach Comber Lake Side canvas Cottage Tent

10.0 out of 10, Exceptional, (56)
"I absolutely love this property! The hosts Richard and Sherry are so kind and make sure you have everything you need! Highly recommend! "
Beach Comber Lake Side canvas Cottage Tent
LakeWay II- 4 min from US-41 and Lake Sullivan
Fridge, microwave, oven, stovetop

LakeWay II- 4 min from US-41 and Lake Sullivan

10.0 out of 10, Exceptional, (4)
"I was traveling in the area to visit family and needed someplace for two nights. The location was perfect. This property combines an interesting historical past (general store built in 1840) and an efficient, comfortable, well thought out home away from home. I recommend it without hesitation!"
LakeWay II- 4 min from US-41 and Lake Sullivan
Castaway lake side canvas cottage scene
Exterior

Castaway lake side canvas cottage scene

10.0 out of 10, Exceptional, (57)
"We had a nice relaxing girls weekend. This is the 2nd time we've stayed there and it has been great both times!"
Castaway lake side canvas cottage scene
Three Lakeside Canvas Cottages group campsite at Parakeet Cove
Terrace/patio

Three Lakeside Canvas Cottages group campsite at Parakeet Cove

10.0 out of 10, Exceptional, (13)
"My family enjoyed our stay, we went fishing, kayaking, swimming. Wonderful, peaceful environment! Definitely would stay again."
Three Lakeside Canvas Cottages group campsite at Parakeet Cove
BEACH STYLE LAKESIDE MINI COTTAGE
Interior

BEACH STYLE LAKESIDE MINI COTTAGE

10.0 out of 10, Exceptional, (84)
"Everything you need for a quiet, relaxing getaway."
BEACH STYLE LAKESIDE MINI COTTAGE
3-bedroom house in adorable Odon with WiFi and AC
Microwave, oven, stovetop, dishwasher

3-bedroom house in adorable Odon with WiFi and AC

10.0 out of 10, Exceptional, (8)
"Nice place, very accommodating, owners were super nice, very clean, highly recommended!"
3-bedroom house in adorable Odon with WiFi and AC
No Wake Zone
Interior

No Wake Zone

10.0 out of 10, Exceptional, (53)
"The property was very clean and the hosts were amazing!"
No Wake Zone
Cozy and relaxing
Fridge, microwave, oven, stovetop

Cozy and relaxing

10.0 out of 10, Exceptional, (7)
"The property was very clean and as advertised. We had a wonderful stay!"
$196 nightly
The price is $220
Sep 8 - Sep 9
Total with taxes and fees
Cozy and relaxing
Eagles Nest Camping Black Creek Cabin
Fridge, microwave, oven, stovetop

Eagles Nest Camping Black Creek Cabin

9.8 out of 10, Exceptional, (18)
"Lovely cabin ,nice setting ,easy parking ,great hosts !😀"
Eagles Nest Camping Black Creek Cabin
Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio
Smart TV, DVD player

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

9.8 out of 10, Exceptional, (10)
"Our overall stay was very nice, property was very clean, decorated nicely, well stocked, and everwhere we needed to go was an easy drive. "
Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio
Jasonville Cabin - Walk to Shakamak State Park!
House (3 Bedrooms) | Interior

Jasonville Cabin - Walk to Shakamak State Park!

2.0 star property
Jasonville Cabin - Walk to Shakamak State Park!
Eagles Nest Camping Bee Hunter Cabin
Outdoor dining

Eagles Nest Camping Bee Hunter Cabin

9.8 out of 10, Exceptional, (35)
"Came for the fishing in the area. This was a great place to stay."
Eagles Nest Camping Bee Hunter Cabin
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

Find out more about Pleasantville

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 $146 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Hillenbrand Hideaway: Visitors like this Pleasantville vacation home rental. It offers a patio, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

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.