Holiday Rentals in Chester County

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Featured Holiday Rentals in Chester County

Country Outback Cozy Home *W/Camp Fire Pit*
Terrace/patio

Country Outback Cozy Home *W/Camp Fire Pit*

9.8 out of 10, Exceptional, (32)
"A very quaint, get-away spot pleasantly and cherfully furnished. A real find!"
The price is €176
includes taxes & fees
21 Jul - 22 Jul
Country Outback Cozy Home *W/Camp Fire Pit*
Ushmila's Nest - Private suite with 2 rooms & Bathroom.
Exterior

Ushmila's Nest - Private suite with 2 rooms & Bathroom.

9.8 out of 10, Exceptional, (41)
"Our stay was very nice. Cute little place and it had everything we needed plus some!"
The price is €166
includes taxes & fees
3 Aug - 4 Aug
Ushmila's Nest - Private suite with 2 rooms & Bathroom.
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Interior

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had an excellent stay"
The price is €220
includes taxes & fees
18 Aug - 19 Aug
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Ushmila's Nest- private entrance, bedroom & bathroom
Outdoor dining

Ushmila's Nest- private entrance, bedroom & bathroom

10.0 out of 10, Exceptional, (33)
"The Nest was a lovely place to stay - cute cottage feel, comfortable bed, all the amenities one could ask for, and great location. Right across from a train station and close by downtown Wayne. We would definitely stay again if we are back in town!"
The price is €177
includes taxes & fees
27 Jul - 28 Jul
Ushmila's Nest- private entrance, bedroom & bathroom
Underground Railroad Barn
Interior

Underground Railroad Barn

9.8 out of 10, Exceptional, (15)
"The barn was lovely and great location! The owner was easy to reach with any question I had. "
The price is €276
includes taxes & fees
5 Aug - 6 Aug
Underground Railroad Barn
Historic Farmhouse in Chester County
Terrace/patio

Historic Farmhouse in Chester County

10.0 out of 10, Exceptional, (3)
"This property was historic but maintained so well it felt very comfortable!"
The price is €238
includes taxes & fees
20 Jul - 21 Jul
Historic Farmhouse in Chester County
Modern Mid-Century Family Retreat
Outdoor dining

Modern Mid-Century Family Retreat

2.5 star property
10.0 out of 10, Exceptional, (11)
"Our family recently spent 4 nights in this beautiful home and our trip was incredible. The house is on a lovely and quiet street, and upon entering we could not get over how clean and orderly everything was! Our hosts were helpful and responsive. We will stay here on all of our future trips to PA!"
The price is €656
includes taxes & fees
22 Jul - 23 Jul
Modern Mid-Century Family Retreat
Homey Retreat in Historic Kennett Square!!
Fridge, microwave, oven, stovetop

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (78)
"So convenient and easy to walk to shops and food! The house is adorable and clean. Looking forward to staying again. "
The price is €343
includes taxes & fees
18 Aug - 19 Aug
Homey Retreat in Historic Kennett Square!!
Homestead Guesthouse
Property grounds

Homestead Guesthouse

10.0 out of 10, Exceptional, (19)
"Property was very clean, comfortable and a very quiet neighborhood."
The price is €287
includes taxes & fees
4 Aug - 5 Aug
Homestead Guesthouse
Kennett Square, Near Longwood Gardens & Downtown
Interior

Kennett Square, Near Longwood Gardens & Downtown

7.8 out of 10, Good, (10)
"Great place, very difficult check in process. It was a nice stay overall "
The price is €442
includes taxes & fees
20 Jul - 21 Jul
Kennett Square, Near Longwood Gardens & Downtown
The Historic Walton House by RPG
Fridge, microwave, oven, stovetop

The Historic Walton House by RPG

10.0 out of 10, Exceptional, (33)
"Very convenient location and well-appointed unit. "
The price is €586
includes taxes & fees
22 Jul - 23 Jul
The Historic Walton House by RPG
Underground Railroad 4 Bedroom Farmhouse
Interior

Underground Railroad 4 Bedroom Farmhouse

9.8 out of 10, Exceptional, (19)
"Great property for a girls' weekend. Super clean, helpful and friendly owner, cute property and grounds, well-maintained."
The price is €350
includes taxes & fees
3 Aug - 4 Aug
Underground Railroad 4 Bedroom Farmhouse
Heritage Haven - West Chester Borough
Fridge, microwave, oven, stovetop

Heritage Haven - West Chester Borough

9.4 out of 10, Exceptional, (3)
"Great place and Michael could not have been more hospitable. "
The price is €404
includes taxes & fees
22 Jul - 23 Jul
Heritage Haven - West Chester Borough
Charming 2-bedroom house Phoenixville
Exterior detail

Charming 2-bedroom house Phoenixville

The price is €199
includes taxes & fees
22 Jul - 23 Jul
Charming 2-bedroom house Phoenixville
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens
Interior

Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens

9.8 out of 10, Exceptional, (38)
"Beautiful property for a group weekend!"
The price is €1,502
includes taxes & fees
20 Jul - 21 Jul
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens
Modern & Cozy 4 bd/3 ba WC convenience!
Interior

Modern & Cozy 4 bd/3 ba WC convenience!

9.6 out of 10, Exceptional, (11)
"The house is comfortable and very clean. Enjoyed our stay"
The price is €505
includes taxes & fees
7 Aug - 8 Aug
Modern & Cozy 4 bd/3 ba WC convenience!
Lovely Private Guesthouse with AC & WiFi in Shillington
Exterior

Lovely Private Guesthouse with AC & WiFi in Shillington

9.6 out of 10, Exceptional, (4)
"5/5 nice and cozy home, host was responsive, would definitely book again!"
The price is €137
includes taxes & fees
20 Jul - 21 Jul
Lovely Private Guesthouse with AC & WiFi in Shillington
Charming 3-bedroom house in welcoming Philadelphia with AC, WiFi
Smart TV

Charming 3-bedroom house in welcoming Philadelphia with AC, WiFi

2.0 star property
9.6 out of 10, Exceptional, (4)
"10/10 would recommend staying here!! The place is incredible and would definitely stay here again when visiting Philly "
The price is €339
includes taxes & fees
3 Aug - 4 Aug
Charming 3-bedroom house in welcoming Philadelphia with AC, WiFi
Cozy hideaway on your own corner of our homestead
Smart TV, fireplace, DVD player, books

Cozy hideaway on your own corner of our homestead

9.8 out of 10, Exceptional, (122)
"This is a great little place, very comfortable, clean, and a great price. Wonderful hostess. Will be back!"
The price is €145
includes taxes & fees
4 Aug - 5 Aug
Cozy hideaway on your own corner of our homestead
The Loft at Riverside
Interior

The Loft at Riverside

9.6 out of 10, Exceptional, (24)
"Super clean, quiet, easy parking, feel like home, definitely will be back soon!"
The price is €141
includes taxes & fees
23 Jul - 24 Jul
The Loft at Riverside
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free