Holiday Rentals in Pleasantville

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Our top choices for Pleasantville holiday rentals

10.0 out of 10, Exceptional, (2)
"Host was very accommodating. Would definitely book again. "
United States
Beth V.
The price is €162
includes taxes & fees
17 Dec - 18 Dec
Pine Oaks Cabin includes Guest Pole Barn. Modern comfort meets county living.

Cottage in Jasonville

No Wake Zone
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
8.8 out of 10, Excellent, (21)
"Perfect for our weekend getaway needs. Very clean, beds were comfortable. Appliances could be upgraded, but were functional. "
United States
Kent W.
Peaceful Cabin By The Lake
9.8 out of 10, Exceptional, (39)
"Great location to stay for hunting "
United States
Devin W.
Eagles Nest Camping Bee Hunter Cabin

Cabin in Jasonville

Lake View Cabin
9.8 out of 10, Exceptional, (84)
"we enjoyed our stay, the cabin is well appointed and comfortable."
United States
Dave S.
Lake View Cabin

Holiday Home in Jasonville

Hillenbrand Hideaway
9.0 out of 10, Wonderful, (10)
"We had fun at the property. The hot tub was the best part. The cabin was cozy."
United States
Janet B.
Hillenbrand Hideaway

Holiday Home in Linton

Cozy and relaxing
9.4 out of 10, Exceptional, (9)
"The property was very clean and as advertised. We had a wonderful stay!"
United States
Jason L.
The price is €202
includes taxes & fees
17 Dec - 18 Dec
Cozy and relaxing
10.0 out of 10, Exceptional, (56)
"A great place to go and get away from the hustle and bustle and relax. Wonderful hosts and very clean property."
United States
Rebecca K.
Beach Comber Lake Side canvas Cottage Tent

Cottage in Linton

Pleasant Grove Farm LLC
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 €124
includes taxes & fees
15 Jan - 16 Jan 2026
Pleasant Grove Farm LLC
10.0 out of 10, Exceptional, (86)
"Relaxing little vacation, definitely going back!"
United States
Kristin A.
BEACH STYLE LAKESIDE MINI COTTAGE
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
10.0 out of 10, Exceptional, (16)
"Great place to stay, clean and comfortable "
United States
Ann G.
The price is €180
includes taxes & fees
17 Dec - 18 Dec
Cozy cottage 4 minutes from Lake Sullivan!
10.0 out of 10, Exceptional, (13)
"Very clean"
United States
Angie W.
3-bedroom house in adorable Odon with WiFi and AC
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
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
2.0 star property
Jasonville Cabin - Walk to Shakamak State Park!
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
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 .
9.8 out of 10, Exceptional, (20)
"Lovely cabin ,nice setting ,easy parking ,great hosts !😀"
United States
Kathleen
Eagles Nest Camping Black Creek Cabin
10.0 out of 10, Exceptional, (18)
"Clean cabin and very peaceful "
United States
ryan p.
Eagles Nest Camping Brewer 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

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, apart-hotels, 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 €124 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?

Cozy and relaxing: This holiday home rental outside of Pleasantville offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

What’s there to see and do in Pleasantville?

While you're exploring the area, Shakamak State Park and Sullivan City 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 County 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.