Holiday Homes in Chester County

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Chester County

Our top choices for Chester County holiday homes

The Sweet Pea 3BD 2BA Cozy, Stylish Stay Just Minutes from I-40 & Everything
Iron/ironing board, WiFi, bed sheets

The Sweet Pea 3BD 2BA Cozy, Stylish Stay Just Minutes from I-40 & Everything

10.0 out of 10, Exceptional, (1)
"Super cute house! Very comfortable and everything was spotless!!! Very convenient location for day trip to Nashville! Would absolutely stay again! "
The Sweet Pea 3BD 2BA Cozy, Stylish Stay Just Minutes from I-40 & Everything
Charming 3-bedroom house with all the amenities located in the heart of Jackson
Private kitchen

Charming 3-bedroom house with all the amenities located in the heart of Jackson

10.0 out of 10, Exceptional, (13)
"Had a wonderful time "
The price is AU$408
includes taxes & fees
7 Sept - 8 Sept
Charming 3-bedroom house with all the amenities located in the heart of Jackson
Single house 3 bed rooms bath kitchen sitting room
Dining

Single house 3 bed rooms bath kitchen sitting room

9.4 out of 10, Exceptional, (22)
"We had a very nice stay here while visiting Shiloh National Battlefield. Communication with the host was very prompt and accommodating!"
The price is AU$360
includes taxes & fees
25 Aug - 26 Aug
Single house 3 bed rooms bath kitchen sitting room
A Gem on the Beautiful Tennessee River: Perfect for gatherings and Retreats
Fridge, microwave, oven, stovetop

A Gem on the Beautiful Tennessee River: Perfect for gatherings and Retreats

A Gem on the Beautiful Tennessee River: Perfect for gatherings and Retreats
Peaceful Getaway In Charming Tiny House
Interior

Peaceful Getaway In Charming Tiny House

10.0 out of 10, Exceptional, (14)
"Beautifully decorated and we had a very peaceful stay here. Very well designed and has everything you need. Very peaceful setting. "
The price is AU$198
includes taxes & fees
26 Aug - 27 Aug
Peaceful Getaway In Charming Tiny House
3 Br; 2 Br house; Edgewater cove; North Jackson, TN, sleeps 6
Smart TV

3 Br; 2 Br house; Edgewater cove; North Jackson, TN, sleeps 6

9.8 out of 10, Exceptional, (49)
"So nice to have room to spend time with family & friends"
The price is AU$368
includes taxes & fees
27 Aug - 28 Aug
3 Br; 2 Br house; Edgewater cove; North Jackson, TN, sleeps 6
Charming 3-bedroom house located in the heart of Jackson.
Smart TV, books

Charming 3-bedroom house located in the heart of Jackson.

10.0 out of 10, Exceptional, (14)
"Great stay. Great price point. If you need to be in the middle of Jackson, TN, this is the spot!"
The price is AU$359
includes taxes & fees
3 Sept - 4 Sept
Charming 3-bedroom house located in the heart of Jackson.
Vacation rental home Lexington
Outdoor dining

Vacation rental home Lexington

10.0 out of 10, Exceptional, (12)
"Nice house in a good location, very friendly and helpful host"
The price is AU$456
includes taxes & fees
25 Aug - 26 Aug
Vacation rental home Lexington
Remodeled N. Jackson Home w/ Shuffleboard, sleeps 6
Smart TV

Remodeled N. Jackson Home w/ Shuffleboard, sleeps 6

9.8 out of 10, Exceptional, (22)
"Great location. Enjoyed the shuffleboard!"
Remodeled N. Jackson Home w/ Shuffleboard, sleeps 6
La Banque Stylish and comfy stay
Dining

La Banque Stylish and comfy stay

10.0 out of 10, Exceptional, (15)
"This old converted bank was quaint and comfortable. We had a great stay and Mali, the host, was nice and attentive. We would stay there again. "
The price is AU$316
includes taxes & fees
24 Sept - 25 Sept
La Banque Stylish and comfy stay
TNN Cozy home away.
Terrace/patio

TNN Cozy home away.

2.0 star property
10.0 out of 10, Exceptional, (4)
"House was clean, check in and check out was easy."
TNN Cozy home away.
Pickwick- Screened Patio ON Tennessee River 7th Nt FREE- Dogs Allowed
Exterior

Pickwick- Screened Patio ON Tennessee River 7th Nt FREE- Dogs Allowed

7.8 out of 10, Good, (6)
"Nice house. We stayed there while attending a youth convention in Savannah. My only complaint is we had to haul off our own trash. When paying 200 in hosting fees, would be nice if trash removal was included."
Pickwick- Screened Patio ON Tennessee River 7th Nt FREE- Dogs Allowed
2-Bedroom Sweet Retreat in Lexington
Fridge, microwave, oven, stovetop

2-Bedroom Sweet Retreat in Lexington

10.0 out of 10, Exceptional, (21)
"We really enjoyed our time here. Despite a short stay and a little issue with the automated door lock, Heather and co took care of us and the place was immaculately cared for! Thanks for a great stay!"
The price is AU$354
includes taxes & fees
28 Aug - 29 Aug
2-Bedroom Sweet Retreat in Lexington
Escape to Tranquility: Scenic Tennessee River Cabin Retreat
Terrace/patio

Escape to Tranquility: Scenic Tennessee River Cabin Retreat

10.0 out of 10, Exceptional, (6)
"Perfect location"
Escape to Tranquility: Scenic Tennessee River Cabin Retreat
Charming 2-bedroom house in Savannah. Be our guest!
Private kitchen

Charming 2-bedroom house in Savannah. Be our guest!

10.0 out of 10, Exceptional, (2)
"We really enjoyed the property. It had everything we needed."
Charming 2-bedroom house in Savannah. Be our guest!
River View & Retreat
Outdoor dining

River View & Retreat

10.0 out of 10, Exceptional, (3)
"Thank you for sharing your home! We enjoyed the River view! It was directly around historic sites and we easily enjoyed day trips from the house! The Catfish Hotel is a must!!"
River View & Retreat
Cozy 2-bedroom house in Savannah. We welcome you!
Private kitchen

Cozy 2-bedroom house in Savannah. We welcome you!

9.0 out of 10, Wonderful, (2)
"Well decorated, comfortable, clean and an excellent location near grocery stores and restaurants. Would definitely stay here again when returning to the area."
Cozy 2-bedroom house in Savannah. We welcome you!
Charming 3-bedroom house in enchanting Jackson with AC, WiFi, private pool
Microwave, oven, stovetop, dishwasher

Charming 3-bedroom house in enchanting Jackson with AC, WiFi, private pool

10.0 out of 10, Exceptional, (8)
"We looked at a lot of properties in the area on vrbo. This one checked most of our boxes. Kids had a great time. If you have little ones, you may want to bring some toys. We ended up getting some side walk chalk, balls, and a frisbee. Overall, a nice getaway fornthe family."
Charming 3-bedroom house in enchanting Jackson with AC, WiFi, private pool
Peaceful Sears, Roebuck and Co. Mail Order Home.
Fridge, microwave, oven, stovetop

Peaceful Sears, Roebuck and Co. Mail Order Home.

9.8 out of 10, Exceptional, (47)
"Love this little house when visiting Freed! "
The price is AU$391
includes taxes & fees
4 Sept - 5 Sept
Peaceful Sears, Roebuck and Co. Mail Order Home.
Guesthouse Front Suite
Dining

Guesthouse Front Suite

10.0 out of 10, Exceptional, (3)
"Wonderful time at this beautiful place. Plenty of space for our group and lots of things to do."
The price is AU$1,446
includes taxes & fees
25 Aug - 26 Aug
Guesthouse Front Suite
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

Residence Inn Jackson

Residence Inn Jackson

10/10 Excellent
"Right on par with the Residence Inn brand "
Guy M. 1-night trip
Posted 2 days ago
Residence Inn Jackson