Pleasantville Holiday Rentals

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Holiday Rentals in Pleasantville

Cottage in Linton

3.0 star property
9.4 out of 10, Exceptional, (101)
"This is our favorite place to stay every Labor Day weekend. It’s home away from home!"
United States
Craig
The price is NZ$255
includes taxes & fees
4 Dec - 5 Dec
Pleasant Grove Farm LLC

Cottage in Jasonville

10.0 out of 10, Exceptional, (57)
"This is our 3rd time staying here and we love it! The vibes are immaculate, property is impeccable, and the host are great people. "
United States
Courtney G.
No Wake Zone

Holiday Home in Jasonville

9.0 out of 10, Wonderful, (8)
"Loved this!! It was super cute and cozy!! "
United States
Breanna
Hillenbrand Hideaway

Cabin in Linton

9.8 out of 10, Exceptional, (20)
"Lovely cabin ,nice setting ,easy parking ,great hosts !😀"
United States
Kathleen
Eagles Nest Camping Black Creek Cabin

Holiday Home in Linton

9.4 out of 10, Exceptional, (8)
"The property was very clean and as advertised. We had a wonderful stay!"
United States
Jason L.
The price is NZ$409
includes taxes & fees
30 Nov - 1 Dec
Cozy and relaxing

Cottage in Jasonville

10.0 out of 10, Exceptional, (57)
"My friend and I stayed here for 2 nights and we had a great time. The cabins are clean and provide basic necessities. The best part is being right on the water! We spent the whole time out fishing and kayaking. The owners were very friendly, helpful and responsive. We will definitely be coming back to stay again!"
United States
Emerson G.
Castaway lake side canvas cottage scene

Cabin in Linton

9.8 out of 10, Exceptional, (39)
"This is the second time that we’ve stayed here. Both times we’ve really enjoyed it and had a nice peaceful stay."
United States
Shad S.
Eagles Nest Camping Bee Hunter Cabin

Holiday Home in Sullivan

10.0 out of 10, Exceptional, (6)
"Super cute, great location, would definitely stay here again "
United States
Melinda S.
The price is NZ$400
includes taxes & fees
4 Dec - 5 Dec
LakeWay II- 4 min from US-41 and Lake Sullivan

Cabin in Jasonville

9.8 out of 10, Exceptional, (82)
"we enjoyed our stay, the cabin is well appointed and comfortable."
United States
Dave S.
Lake View Cabin

Cottage in Jasonville

10.0 out of 10, Exceptional, (56)
"This was our second time staying here. It was even better than the last time. Fishing, swimming, kayaking, and then relaxing in the ac so we can do it all again. We will be back again"
United States
Shane M.
Beach Comber Lake Side canvas Cottage Tent

Cottage in Jasonville

10.0 out of 10, Exceptional, (86)
"Relaxing little vacation, definitely going back!"
United States
Kristin A.
BEACH STYLE LAKESIDE MINI COTTAGE

Cabin in Bloomfield

10.0 out of 10, Exceptional, (51)
"Aleta and the cabin were very helpful and clean. This was a great spot for a weekend get away."
United States
Charles
Private, cozy cabin on 13 acres with two ponds

Cabin in Linton

8.8 out of 10, Excellent, (20)
"The beds were very comfortable. Loved roasting marshmallows over an open fire. Having a grill was great. I highly recommend this cabin."
United States
Barbara S.
Peaceful Cabin By The Lake

Cabin in Jasonville

10.0 out of 10, Exceptional, (1)
"Very cozy, great place to stay with family or friends. Excellent view of the stars with a fire pit in the yard! "
United States
Bryan H.
Quiet Country Cabin • Near Trails & State Parks

Cottage in Sullivan

10.0 out of 10, Exceptional, (16)
"Great place to stay, clean and comfortable "
United States
Ann G.
The price is NZ$360
includes taxes & fees
3 Dec - 4 Dec
Cozy cottage 4 minutes from Lake Sullivan!

Cottage in Jasonville

2.0 star property
Jasonville Cabin - Walk to Shakamak State Park!

Holiday Home in Odon

10.0 out of 10, Exceptional, (13)
"Very clean"
United States
Angie W.
3-bedroom house in adorable Odon with WiFi and AC

Cabin in Jasonville

9.8 out of 10, Exceptional, (18)
"This has SO much more than what meets the eye. I stayed here with my Dad, Brother and nephew for my dad’s birthday and is 10 minutes from Redbird offroad park. Gloria was very hospitable and more than happy to accommodate in any way possible. We will definitely be back. Thank you again for the hospitality Gloria!!"
United States
Blake R.
Unique cozy 14x40 Cabin with a nice deck by the water .

Cottage in Jasonville

10.0 out of 10, Exceptional, (13)
"This place was awesome!! We would highly recommend! The owners were great! This fishing was outstanding. The only complaint I have is we didn’t stay long enough. We will be back!"
United States
dustin b.
Three Lakeside Canvas Cottages group campsite at Parakeet Cove

Holiday Home in Linton

10.0 out of 10, Exceptional, (11)
"The property was great. It was very quiet and had everything we needed."
United States
Joyce E.
Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio
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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Find out more about Pleasantville

Everything you need to know about Pleasantville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasantville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pleasantville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasantville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasantville holiday rentals we have selected for you start as low as NZ$255 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pleasantville rentals

At Expedia, we put the best Pleasantville holiday 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 holiday.

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 holiday rentals in Pleasantville?

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

What are some of the best holiday rentals that Pleasantville has to offer?

Hillenbrand Hideaway: This holiday home rental outside of Pleasantville offers a patio, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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 wider area, you’ll find Elks Country Club and Sullivan City Park.

What’s a holiday rental in Pleasantville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pleasantville. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.