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Holiday Rentals in Chester County

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Our top choices for Chester County holiday rentals

A living room with a flat-screen TV, a wooden cabinet, a round ottoman, a ceiling fan, and a dining area in the background.

1. Little Green Cottage in Henderson

Little Green Cottage in Henderson
Henderson
9.0 out of 10, Wonderful, (4 reviews)
"This is a cute house with a great kitchen and convenient location!"
United States
Holly M.
The price is €220
includes taxes & fees
16 Nov - 17 Nov
Little Green Cottage in Henderson
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with white chairs and a wooden table.

2. 3 bedroom 2 bath home a few blocks away from FHU.

3 bedroom 2 bath home a few blocks away from FHU.
Henderson
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place. Loved our stay."
United States
julie
The price is €183
includes taxes & fees
17 Nov - 18 Nov
3 bedroom 2 bath home a few blocks away from FHU.
A large, single-story building with a metal roof and wooden siding, featuring a garage and a covered porch area.

3. Kid friendly vacation home with pool and garage bonus area with a pool table!

Kid friendly vacation home with pool and garage bonus area with a pool table!
Henderson
9.8 out of 10, Exceptional, (8 reviews)
"The house was so beautiful and had everything we needed. Our stay was perfect and the pool is fabulous! Will be staying there again next time we're in Tennessee!"
United States
James C.
The price is €638
includes taxes & fees
24 Nov - 25 Nov
Kid friendly vacation home with pool and garage bonus area with a pool table!
An outdoor seating area with chairs and potted plants, a glass wall, and a view of the interior.

4. StudioRes by Marriott Jackson, TN

StudioRes by Marriott Jackson, TN
3.0 star property
Jackson
8.6 out of 10, Excellent, (53 reviews)
"We really enjoyed our stay! It had almost every thing we needed. The bed was very comfortable, and living area had plenty of room. You will need to bring your own shampoo, conditioner, soap and hair dryer. The staff were very friendly and helpful."
United States
David
The price is €95
includes taxes & fees
16 Nov - 17 Nov
StudioRes by Marriott Jackson, TN
Private kitchen

5. stayAPT Suites Jackson

stayAPT Suites Jackson
3.5 star property
Jackson
8.4 out of 10, Very good, (225 reviews)
"This place is tremendous! Love everything about it!"
United States
Joyce
The price is €98
includes taxes & fees
26 Nov - 27 Nov
stayAPT Suites Jackson
A cozy cabin interior with a gray sofa, wooden shelves with various decorations, and a rustic ceiling.

6. Peaceful Getaway In Charming Tiny House

Peaceful Getaway In Charming Tiny House
Hornsby
10.0 out of 10, Exceptional, (33 reviews)
"Great spot for what I needed. I enjoyed my stay! The host was wonderful and even provided the coolest welcome basket. "
United States
Taylor B.
The price is €97
includes taxes & fees
15 Nov - 16 Nov
Peaceful Getaway In Charming Tiny House
A cozy cabin interior with a wooden interior, a sofa, a chair, and a kitchen area with a stove and microwave.

7. 2-Bedroom Tiny Home with full kitchen, laundry, wifi, and beautiful pond views

2-Bedroom Tiny Home with full kitchen, laundry, wifi, and beautiful pond views
Adamsville
10.0 out of 10, Exceptional, (34 reviews)
"Very nice cabin to have some downtime during a busy weekend."
United States
Melissa
The price is €167
includes taxes & fees
15 Nov - 16 Nov
2-Bedroom Tiny Home with full kitchen, laundry, wifi, and beautiful pond views
A brick wall with a hanging pendant light, a door, and a brick fireplace with a painting.

8. La Banque Stylish and comfy stay

La Banque Stylish and comfy stay
Finger
10.0 out of 10, Exceptional, (37 reviews)
"The place was too notch. We loved our short time there and will definitely be back if ever in the area again."
United States
Tiffany B.
The price is €166
includes taxes & fees
18 Nov - 19 Nov
La Banque Stylish and comfy stay
A cozy cabin interior with a living room, a sofa, a patterned armchair, a kitchen area with a refrigerator, stove, and window with curtains.

9. Country Cabin in the Woods

Country Cabin in the Woods
Lexington
10.0 out of 10, Exceptional, (69 reviews)
"Wonderful place, clean & cozy Everything was perfect, would stay here again"
United States
Angela K.
The price is €136
includes taxes & fees
25 Nov - 26 Nov
Country Cabin in the Woods
A modern living room with a sofa, chairs, a coffee table, and a view of the outside.

10. Cozy, Clean, 2-bedroom 1 bathroom home in Lexington, TN

Cozy, Clean, 2-bedroom 1 bathroom home in Lexington, TN
Lexington
The price is €275
includes taxes & fees
15 Nov - 16 Nov
Cozy, Clean, 2-bedroom 1 bathroom home in Lexington, TN
A cozy wooden room with a bed, a grey ottoman, and two armchairs.

11. Tiny home cabin by the pond

Tiny home cabin by the pond
Adamsville
9.8 out of 10, Exceptional, (64 reviews)
"It was clean and clean comfortable for us and our dogs. Very quiet and peaceful with nice surroundings!"
United States
Warren
The price is €142
includes taxes & fees
1 Dec - 2 Dec
Tiny home cabin by the pond
A wooden interior with a dining table, chairs, a kitchen area, and a living space.

12. Grannies house sits on 300 acre farm built in 1959

Grannies house sits on 300 acre farm built in 1959
Finger
9.8 out of 10, Exceptional, (18 reviews)
"Very clean , comfortable beds , cozy place and peaceful."
United States
Kevin R.
The price is €286
includes taxes & fees
15 Nov - 16 Nov
Grannies house sits on 300 acre farm built in 1959
A living room with a sofa, striped armchairs, a fireplace, and a decorative rug.

13. Charming 1-bedroom Pearl Cottage with WiFi in the historic Casey Jones Village

Charming 1-bedroom Pearl Cottage with WiFi in the historic Casey Jones Village
Jackson
9.8 out of 10, Exceptional, (13 reviews)
"Very pretty decor...spacious room and bathroom. Wrap around porch and a walk to the old country store which is full of all kinds of souvenirs. Great place for a couple to enjoy a time away."
United States
Lindi
The price is €215
includes taxes & fees
15 Nov - 16 Nov
Charming 1-bedroom Pearl Cottage with WiFi in the historic Casey Jones Village
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a built-in oven. There are three wooden stools with cushioned seats.

14. 2-Bedroom Sweet Retreat in Lexington

2-Bedroom Sweet Retreat in Lexington
Lexington
10.0 out of 10, Exceptional, (40 reviews)
"Nice property"
United States
Scott S.
The price is €194
includes taxes & fees
16 Nov - 17 Nov
2-Bedroom Sweet Retreat in Lexington
An outdoor deck with a wooden table and chairs, string lights, and a covered area with a view of the backyard.

15. Vacation rental home Lexington

Vacation rental home Lexington
Lexington
9.8 out of 10, Exceptional, (16 reviews)
"Nice house in a good location, very friendly and helpful host"
United States
Stan S.
The price is €238
includes taxes & fees
16 Nov - 17 Nov
Vacation rental home Lexington
A porch with red wooden columns, a swing chair, and a rocking chair.

16. Old Tennessee Homeplace between Jackson and Lexington, TN, 12 minutes from I-40

Old Tennessee Homeplace between Jackson and Lexington, TN, 12 minutes from I-40
Lexington
8.8 out of 10, Excellent, (3 reviews)
"Cute house nice area could use some better cooking pans, knives, and utensils we don’t like to eat out a lot and would rather cook so was a little disappointed in the kitchen accessories other than that a beautiful place "
United States
Jennifer B.
The price is €267
includes taxes & fees
16 Nov - 17 Nov
Old Tennessee Homeplace between Jackson and Lexington, TN, 12 minutes from I-40
A wooden cabin with a balcony, surrounded by a forest.

17. Cozy Cabin Hidden in Amish Country

Cozy Cabin Hidden in Amish Country
Stantonville
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful well stock cabin we love everything about itI will rent again next time we visit our family in the area "
United States
Jackie I.
The price is €301
includes taxes & fees
15 Nov - 16 Nov
Cozy Cabin Hidden in Amish Country
A two-story house with a stone facade, a front porch, and a garage.

18. Urban Oasis

Urban Oasis
Jackson
10.0 out of 10, Exceptional, (2 reviews)
"Perfect home"
United States
Jeff V.
Urban Oasis
A living room with a brick fireplace, leather sofas, a flat-screen TV, and a large window with blinds.

19. Cozy 2-bedroom cabin in charming Lexington with WiFi, AC

Cozy 2-bedroom cabin in charming Lexington with WiFi, AC
Lexington
10.0 out of 10, Exceptional, (15 reviews)
"Awesome property. House was very comfortable. Will definitely stay again."
United States
Kay P.
The price is €266
includes taxes & fees
13 Dec - 14 Dec
Cozy 2-bedroom cabin in charming Lexington with WiFi, AC
A modern kitchen with a stainless steel refrigerator, a microwave, and a gas stove.

20. Stylish Home with Infrared Sauna, 1 M from I-40, near Rockabilly Ball Stadium

Stylish Home with Infrared Sauna, 1 M from I-40, near Rockabilly Ball Stadium
Jackson
10.0 out of 10, Exceptional, (1 review)
"If you choose to stay here, make sure to leave it as you found it; otherwise, don’t stay. This home is akin to a five-star hotel—absolutely beautiful."
United States
Samira F.
The price is €393
includes taxes & fees
15 Nov - 16 Nov
Stylish Home with Infrared Sauna, 1 M from I-40, near Rockabilly Ball Stadium
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 Chester County Hotel Reviews

Best Western Plus Executive Residency Jackson Northeast

Best Western Plus Executive Residency Jackson Northeast

10/10 Excellent
"Very clean, staff friendly, and the best breakfast at any hotel I’ve stayed at with the most food options."
Bethanne 1-night trip
Posted less than an hour ago
Best Western Plus Executive Residency Jackson Northeast

Find out more about Chester County

Holiday Homes in Chester County

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