Pleasantville Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
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In four months
Mar 27 - Mar 29

Vacation Rentals in Pleasantville

Exterior
Cozy & private 2-bedroom home in Hohenwald, TN only 4miles to the Natchez Trace

Cozy & private 2-bedroom home in Hohenwald, TN only 4miles to the Natchez Trace

2.0 star property
Hohenwald
9.0 out of 10, Wonderful, (2)
"Spent a nice thanksgiving with family at this cozy house. Great location to where we need to be. The house is clean and tidy; got everything we needed. Would come back again! "
United States
rosette v.
The price is ￥11,045
￥25,958 total
includes taxes & fees
Dec 7 - Dec 8
Cozy & private 2-bedroom home in Hohenwald, TN only 4miles to the Natchez Trace
Lake
Peaceful Hills Retreat’s cottage is clean and cozy with a creek on 97 acres

Peaceful Hills Retreat’s cottage is clean and cozy with a creek on 97 acres

Centerville
10.0 out of 10, Exceptional, (91)
"We had a great time at the Cottage. It was a beautiful remote location and a very clean home. Kitchen was well stocked. Jennifer made sure we had everything we needed. Great stay!"
United States
Tammie H.
The price is ￥14,939
￥38,513 total
includes taxes & fees
Dec 8 - Dec 9
Peaceful Hills Retreat’s cottage is clean and cozy with a creek on 97 acres
Interior
Peaceful Hills Retreat Lodge with a Great View, a Pond, a Fireplace, Sleeps 10.

Peaceful Hills Retreat Lodge with a Great View, a Pond, a Fireplace, Sleeps 10.

Centerville
10.0 out of 10, Exceptional, (117)
"Check-in was great and had a wonderful kitchen! "
United States
Samuel W.
The price is ￥17,871
￥46,522 total
includes taxes & fees
Dec 8 - Dec 9
Peaceful Hills Retreat Lodge with a Great View, a Pond, a Fireplace, Sleeps 10.
Fridge, microwave, oven, stovetop
Guest house in Hurricane Mills

Guest house in Hurricane Mills

Hurricane Mills
10.0 out of 10, Exceptional, (4)
"Fit our needs perfectly. We were in town for work & best spot to relax after long days on our feet. We found everything very clean and such a quiet peaceful area. "
United States
Karen L.
The price is ￥15,358
￥30,913 total
includes taxes & fees
Dec 7 - Dec 8
Guest house in Hurricane Mills
Smart TV, fireplace, stereo
Cozy Cabin Getaway on Buffalo River with HUGE Patio

Cozy Cabin Getaway on Buffalo River with HUGE Patio

Lobelville
10.0 out of 10, Exceptional, (11)
"Quite small town. Loved our stay."
United States
James B.
The price is ￥15,358
￥43,275 total
includes taxes & fees
Dec 15 - Dec 16
Cozy Cabin Getaway on Buffalo River with HUGE Patio
Fridge, microwave, oven, stovetop
River Run Cottage at Horseshoe Bend Farm

River Run Cottage at Horseshoe Bend Farm

Centerville
10.0 out of 10, Exceptional, (7)
"If you’re looking for a clean, tastefully decorated and remote experience this is the place for you! We enjoyed the secluded location with fantastic views and open starry skies. The listing is spot on. Perfect for a couple."
United States
Lorraine D.
The price is ￥23,270
￥40,102 total
includes taxes & fees
Dec 7 - Dec 8
River Run Cottage at Horseshoe Bend Farm
Exterior
Spectalur Bez Valley Farm

Spectalur Bez Valley Farm

Nunnelly
9.6 out of 10, Exceptional, (94)
"Beautiful property with great owners!"
United States
Michael P.
The price is ￥32,577
￥68,125 total
includes taxes & fees
Dec 7 - Dec 8
Spectalur Bez Valley Farm
Outdoor dining
Great Hunting, Fishing and Family Vacation Getaway

Great Hunting, Fishing and Family Vacation Getaway

Linden
9.4 out of 10, Exceptional, (43)
"Beautiful quiet area. Home had everything you need for your stay. The beds were comfortable and appreciated the use of the boats. Taya had great communication. "
United States
J&M F.
The price is ￥20,167
￥36,006 total
includes taxes & fees
Dec 8 - Dec 9
Great Hunting, Fishing and Family Vacation Getaway
Pool
Getaway to the Red House

Getaway to the Red House

2.0 star property
Waynesboro
7.0 out of 10, Good, (2)
"Great little cabin with beautiful scenery."
United States
Amy W.
The price is ￥20,165
￥29,802 total
includes taxes & fees
Dec 7 - Dec 8
Getaway to the Red House
Exterior
Colorful & Cozy River Retreat with a View

Colorful & Cozy River Retreat with a View

Lobelville
9.0 out of 10, Wonderful, (14)
"We wished we could take the swings on the porch home with us. My sister and I were here for a week, and it was super comfortable. We play a lot of board games, for which the turret was perfect. Also, the natural light is great. A box fan helps with air circulation in the closet bedroom. As others have noted, beds are firm and could use some padding for those of us who are older. Road is very close and road noise will be heard at night. Earplugs help. Shower is just perfect and does have some...
United States
Janet H.
The price is ￥15,358
￥47,006 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Colorful & Cozy River Retreat with a View
Exterior
Cute Little Cabin

Cute Little Cabin

Centerville
10.0 out of 10, Exceptional, (5)
"I will say the pictures make it look as if the home is in a secluded setting, which it isn't. That being said the neighborhood it is in is quiet and charming and is pure small town. Perfect place for a couple as it is small and cozy as described. Jennifer the owner was quick to respond to any concerns and went the extra mile to make sure we had the check in info when VRBO's system glitched. Would book this again in an instant!"
United States
David G.
The price is ￥23,270
￥44,552 total
includes taxes & fees
Dec 7 - Dec 8
Cute Little Cabin
TV, fireplace
Cozy lake front hide away

Cozy lake front hide away

2.0 star property
Linden
The price is ￥18,616
￥43,600 total
includes taxes & fees
Dec 21 - Dec 22
Cozy lake front hide away
Pool
Frank's Retreat Cherokee Rd

Frank's Retreat Cherokee Rd

Waynesboro
The price is ￥31,026
￥39,636 total
includes taxes & fees
Dec 14 - Dec 15
Frank's Retreat Cherokee Rd
Pool
Getaway at Springer's Catch!

Getaway at Springer's Catch!

2.0 star property
Waynesboro
The price is ￥20,191
￥29,840 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Getaway at Springer's Catch!
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

Cozy & private 2-bedroom home in Hohenwald, TN only 4miles to the Natchez Trace

Cozy & private 2-bedroom home in Hohenwald, TN only 4miles to the Natchez Trace

10/10 Excellent
"Spent a nice thanksgiving with family at this cozy house. Great location to where we need to be. The house is clean and tidy; got everything we needed. Would come back again! "
rosette v. 3-night trip
Posted 6 days ago
Cozy & private 2-bedroom home in Hohenwald, TN only 4miles to the Natchez Trace

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

Are there vacation rentals in Pleasantville?

Yes, we give you a choice of vacation rentals close to the most popular attractions in Pleasantville, or you can choose a secluded option if you're looking for a relaxing stay.

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

Fisherman's River Hideaway with private dock: This vacation home rental outside of Pleasantville is located on a river and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Pleasantville?

Explore the area and family-friendly sights such as C.A. Thompson Park, or get out into nature at a spot like Lewis State Forest. In the larger area, you’ll find Buffalo River Country Club and Grinder's Switch Winery.

What’s a vacation rental in Pleasantville like?

Vacation rentals are private properties you can stay in for a couple of days or more in Pleasantville. Vacation rentals provide amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.