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Chester County Holiday Rentals

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Our top choices for Chester County holiday rentals

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 NZ$435
includes taxes & fees
16 Nov - 17 Nov
Little Green Cottage in Henderson

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 NZ$360
includes taxes & fees
17 Nov - 18 Nov
3 bedroom 2 bath home a few blocks away from FHU.

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 NZ$1,249
includes taxes & fees
24 Nov - 25 Nov
Kid friendly vacation home with pool and garage bonus area with a pool table!

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 NZ$188
includes taxes & fees
15 Dec - 16 Dec
StudioRes by Marriott Jackson, TN

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 NZ$195
includes taxes & fees
15 Dec - 16 Dec
stayAPT Suites Jackson

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 NZ$206
includes taxes & fees
15 Dec - 16 Dec
Peaceful Getaway In Charming Tiny House

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 NZ$327
includes taxes & fees
15 Nov - 16 Nov
2-Bedroom Tiny Home with full kitchen, laundry, wifi, and beautiful pond views

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 NZ$327
includes taxes & fees
18 Nov - 19 Nov
La Banque Stylish and comfy stay

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 NZ$266
includes taxes & fees
25 Nov - 26 Nov
Country Cabin in the Woods

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 NZ$534
includes taxes & fees
23 Nov - 24 Nov
Cozy, Clean, 2-bedroom 1 bathroom home in Lexington, TN

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 NZ$279
includes taxes & fees
1 Dec - 2 Dec
Tiny home cabin by the pond

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 NZ$559
includes taxes & fees
24 Nov - 25 Nov
Grannies house sits on 300 acre farm built in 1959

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 NZ$413
includes taxes & fees
15 Dec - 16 Dec
Charming 1-bedroom Pearl Cottage with WiFi in the historic Casey Jones Village

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 NZ$377
includes taxes & fees
16 Nov - 17 Nov
2-Bedroom Sweet Retreat in Lexington

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 NZ$480
includes taxes & fees
16 Nov - 17 Nov
Vacation rental home Lexington

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 NZ$520
includes taxes & fees
16 Nov - 17 Nov
Old Tennessee Homeplace between Jackson and Lexington, TN, 12 minutes from I-40

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 NZ$590
includes taxes & fees
16 Nov - 17 Nov
Cozy Cabin Hidden in Amish Country

18. Urban Oasis

Urban Oasis
Jackson
10.0 out of 10, Exceptional, (2 reviews)
"Perfect home"
United States
Jeff V.
The price is NZ$569
includes taxes & fees
16 Nov - 17 Nov
Urban Oasis

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 NZ$517
includes taxes & fees
15 Nov - 16 Nov
Cozy 2-bedroom cabin in charming Lexington with WiFi, AC

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 NZ$763
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

Find out more about Chester County

Everything you need to know about Chester County 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 Chester County 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 Chester County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester County. 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 Chester County 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 Chester County holiday rentals we have selected for you start as low as NZ$114 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester County rentals

At Expedia, we put the best Chester County 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 Chester County 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 Chester County 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 Chester County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.