Pleasantville Holiday Rentals

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Holiday Rentals in Pleasantville

Private, cozy cabin on 13 acres with two ponds
TV, fireplace, DVD player, video library

Private, cozy cabin on 13 acres with two ponds

10.0 out of 10, Exceptional, (35)
"Quaint rustic cabin with all the comforts of home including a gas fireplace for chilly October evenings! We thoroughly enjoyed the property and ponds and had a blast fishing for bluegill. Our group of 9 made good use of the HUGE kitchen island where we shared meals and chatted and played card games. Close to Redbird Offroad Rec Area which was the reason for our visit! The big trailer could access the driveway from only one direction and parking was a bit tight but we made it work! "
Private, cozy cabin on 13 acres with two ponds
Pleasant Grove Farm LLC
Cottage, Ensuite (Quail Run Cottage) | Exterior

Pleasant Grove Farm LLC

3.0 star property
9.2 out of 10, Wonderful, (96)
"We can’t wait to come back!"
The price is AU$225
includes taxes & fees
1 Dec - 2 Dec
Pleasant Grove Farm LLC
Cozy and relaxing
Fridge, microwave, oven, stovetop

Cozy and relaxing

10.0 out of 10, Exceptional, (6)
"We were in town for a family funeral. This home was perfect for our family. Such a great home. Comfortable, cozy and very nice. The Host was very easy communicate with and was very accommodating. Highly recommend!"
The price is AU$392
includes taxes & fees
1 Dec - 2 Dec
Cozy and relaxing
Lake View Cabin
Exterior

Lake View Cabin

9.8 out of 10, Exceptional, (69)
"Wonderful stay, beautiful cabin and scenery"
Lake View Cabin
Eagles Nest Camping Bee Hunter Cabin
Outdoor dining

Eagles Nest Camping Bee Hunter Cabin

9.8 out of 10, Exceptional, (31)
"Clean and had everything we needed"
Eagles Nest Camping Bee Hunter Cabin
BEACH STYLE LAKESIDE MINI COTTAGE
Aerial view

BEACH STYLE LAKESIDE MINI COTTAGE

10.0 out of 10, Exceptional, (81)
"The place is Amazing and Richard the owner greeted us with such great hospitality and kindness. It’s a hidden gem from the moment you arrive you are in Aweeee with the lake setting and the wildlife that surrounds you. It’s the perfect place to get away and have time alone with your spouse or Family . I would highly recommend this property. "
BEACH STYLE LAKESIDE MINI COTTAGE
Hillenbrand Hideaway- perfectly located!
Interior

Hillenbrand Hideaway- perfectly located!

10.0 out of 10, Exceptional, (11)
"Very relaxing after a long day in the woods"
Hillenbrand Hideaway- perfectly located!
Beach Comber Lake Side canvas Cottage Tent
Aerial view

Beach Comber Lake Side canvas Cottage Tent

10.0 out of 10, Exceptional, (54)
"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
Castaway lake side canvas cottage scene
Exterior

Castaway lake side canvas cottage scene

10.0 out of 10, Exceptional, (54)
"We visit every year. Sometimes twice. Great place to get away and relax, fish, swim, kayak, cookout etc. truly a hidden gem"
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, (10)
"Loved staying on the property. Bathroom, beds, AC, etc worked as expected. Kayaks and Jon boat usage was smooth. My entire family loved it and want to come back every summer"
Three Lakeside Canvas Cottages group campsite at Parakeet Cove
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, (14)
"Beautiful, quaint, quiet and perfect place to get away from too busy hotels! We loved it and Gloria was fabulous! 5 stars on every thing. Can't wait to go back and stay longer!"
Unique cozy 14x40 Cabin with a nice deck by the water .
Eagles Nest Camping Black Creek Cabin
Aerial view

Eagles Nest Camping Black Creek Cabin

9.8 out of 10, Exceptional, (18)
"Property as described in listing.. Small campground in a remote area but still close to town! We had everything we needed for our short getaway weekend. We enjoyed our stay here!! Thank you to the hosts!"
Eagles Nest Camping Black Creek Cabin
No Wake Zone
Aerial view

No Wake Zone

10.0 out of 10, Exceptional, (50)
"What a great place. I just hope it doesn’t get too popular from all of the raving reviews!! "
No Wake Zone
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, (2)
"Super cute, great location, would definitely stay here again "
LakeWay II- 4 min from US-41 and Lake Sullivan
Eagles Nest Camping Brewer Cabin
Aerial view

Eagles Nest Camping Brewer Cabin

10.0 out of 10, Exceptional, (15)
"New condition, well appointed, good stay"
Eagles Nest Camping Brewer Cabin
Peaceful Cabin By The Lake
Lake

Peaceful Cabin By The Lake

9.0 out of 10, Wonderful, (13)
"Cabin was perfect. The only let down was the pond which was overgrown with moss and was unable to catch any big fish. "
Peaceful Cabin By The Lake
Jasonville Cabin - Walk to Shakamak State Park!
Fridge, microwave, stovetop, dishwasher

Jasonville Cabin - Walk to Shakamak State Park!

9.6 out of 10, Exceptional, (22)
"Very peaceful and relaxing stay"
Jasonville Cabin - Walk to Shakamak State Park!
Cozy cottage 4 minutes from Lake Sullivan!
Interior detail

Cozy cottage 4 minutes from Lake Sullivan!

10.0 out of 10, Exceptional, (11)
"The place was great and the host was great, I don’t think it was obvious that it is connected to a bait shop (shares a wall) and basically in the parking lot of a Dairy Queen. So it’s loud traffic until midnight"
Cozy cottage 4 minutes from Lake Sullivan!
Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio
Living area

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

10.0 out of 10, Exceptional, (4)
"Nice clean place. Owners very easy to communicate with. If in the area definitely stay here!"
Couples' Hideaway - Relaxing barndominium with hammock, firepit, & covered patio
Beautiful Suite with separate bedroom, great room, bathroom.
Interior

Beautiful Suite with separate bedroom, great room, bathroom.

Beautiful Suite with separate bedroom, great room, bathroom.
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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Other types of properties in Pleasantville you may be interested in

Days Inn by Wyndham Sullivan
Desk, blackout curtains, iron/ironing board, free cots/infant beds

Days Inn by Wyndham Sullivan

2.0 star property
7.6 out of 10, Good, (340)
"nice clean rooms "
The price is AU$148
includes taxes & fees
2 Dec - 3 Dec
Days Inn by Wyndham Sullivan
Private, cozy cabin on 13 acres with two ponds
TV, fireplace, DVD player, video library

Private, cozy cabin on 13 acres with two ponds

10.0 out of 10, Exceptional, (35)
"Quaint rustic cabin with all the comforts of home including a gas fireplace for chilly October evenings! We thoroughly enjoyed the property and ponds and had a blast fishing for bluegill. Our group of 9 made good use of the HUGE kitchen island where we shared meals and chatted and played card games. Close to Redbird Offroad Rec Area which was the reason for our visit! The big trailer could access the driveway from only one direction and parking was a bit tight but we made it work! "
Private, cozy cabin on 13 acres with two ponds
Eagles Nest Camping Bee Hunter Cabin
Outdoor dining

Eagles Nest Camping Bee Hunter Cabin

9.8 out of 10, Exceptional, (31)
"Clean and had everything we needed"
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.
Beautiful view of the beach with palm trees

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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, 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 Sullivan County Courthouse 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.