Chester County Holiday Rentals

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Top cities in Chester County

A street lined with historic buildings, a sign for Kildogge's Pub, and a banner for West Chester Restaurant Week.
Vacation Rentals

West Chester

West Chester

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chester County holiday rentals

A wooden deck with a railing, surrounded by lush greenery and trees.

1. Spacious 1-bedroom suite surrounded by nature in charming Downingtown.

Spacious 1-bedroom suite surrounded by nature in charming Downingtown.
Downingtown
10.0 out of 10, Exceptional, (2 reviews)
"Great place for 2 just outside the town of West Chester, would definitely stay again!"
United States
Natasha A.
The price is AU$226
includes taxes & fees
12 Nov - 13 Nov
Spacious 1-bedroom suite surrounded by nature in charming Downingtown.
A covered patio area with a wooden bench, a small bar area, and a staircase leading to an upper level.

2. Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (45 reviews)
"A truly lovely place, really so comfortable, and only a few minutes from the heart of Kennett Square. This is a great stay near many wonderful spots to enjoy in the area. Host was very responsive and helpful!"
United States
Susan & Elton F.
The price is AU$435
includes taxes & fees
15 Nov - 16 Nov
Underground Railroad Barn
A covered deck with outdoor furniture, a white fence, and a view of a green landscape.

3. Black Horse - FarmGuest House A Travelers Rest and a Vacationers Haven

Black Horse - FarmGuest House A Travelers Rest and a Vacationers Haven
Parkesburg
10.0 out of 10, Exceptional, (201 reviews)
"A cozy home away from home with a full kitchen, two bedrooms and two bathrooms. It was the perfect size and floor plan for an almost empty nester couple and our youngest adult son."
United States
Craig Z.
The price is AU$346
includes taxes & fees
9 Nov - 10 Nov
Black Horse - FarmGuest House A Travelers Rest and a Vacationers Haven
A modern kitchen with a central island, bar stools, wooden cabinets, and a large window.

4. Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
10.0 out of 10, Exceptional, (35 reviews)
"Comfortable, clean, thoughtfully stocked property. We would definitely stay again!"
United States
Amy Y.
The price is AU$441
includes taxes & fees
8 Nov - 9 Nov
Underground Railroad 4 Bedroom Farmhouse
A living room with a sofa, a television, and shelves with books and decorative items.

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

Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Nottingham
9.6 out of 10, Exceptional, (25 reviews)
"Great rustic setting for a perfect weekend getaway!"
United States
Emily D.
The price is AU$333
includes taxes & fees
12 Nov - 13 Nov
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
A modern interior with a sofa, a coffee table, and a kitchen area with a dining set.

6. Country Outback Cozy Home *W/Camp Fire Pit*

Country Outback Cozy Home *W/Camp Fire Pit*
Parkesburg
9.8 out of 10, Exceptional, (49 reviews)
"Perfect for two couples to take in a show at sight and sound and take in the area "
United States
Gail H.
The price is AU$304
includes taxes & fees
17 Nov - 18 Nov
Country Outback Cozy Home *W/Camp Fire Pit*
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

7. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (2 reviews)
"My girlfriend and I were in town for a wedding and the VRBO was perfect. Great privacy, lovely decor, and comfortable bed. A full use kitchen was great to have. Cheech (the pig!!) was so friendly and the host even dropped off carrots for us to feed him. The host responded to every question in a timely manner and check in and check out were painless."
United States
Zachary Z.
The price is AU$268
includes taxes & fees
8 Nov - 9 Nov
Cozy 1-bedroom apartment in Lincoln University
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

8. Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.6 out of 10, Excellent, (26 reviews)
"Linda's home is perfect for family traveling! Everything you need for cooking, washing, and just enjoying. The back yard and Patio were awesome for Thunderstorm watching. We'll be back !"
United States
Patricia T.
The price is AU$613
includes taxes & fees
9 Nov - 10 Nov
Kennett Square, Near Longwood Gardens & Downtown
A small wooden structure with a sloped roof, surrounded by a well-maintained garden with various plants and flowers.

9. Solid Rock Homestead Guest House. On the Farm. Enjoy the Animals!

Solid Rock Homestead Guest House. On the Farm. Enjoy the Animals!
Honey Brook
10.0 out of 10, Exceptional, (105 reviews)
"Beautiful rooms and property. Maybe a little small for more than two people."
United States
Rebecca S.
The price is AU$421
includes taxes & fees
1 Dec - 2 Dec
Solid Rock Homestead Guest House. On the Farm. Enjoy the Animals!
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a tiled backsplash.

10. Cottage 3BR Near Longwood Gardens

Cottage 3BR Near Longwood Gardens
Avondale
The price is AU$494
includes taxes & fees
7 Nov - 8 Nov
Cottage 3BR Near Longwood Gardens
A living room with a brick fireplace, a beige sofa, and a wooden coffee table.

11. Off The Beaten Path - Choose This Private Gem

Off The Beaten Path - Choose This Private Gem
Devon
9.8 out of 10, Exceptional, (7 reviews)
"An excellent place to stay in the Philly suburbs. -Great communication with the host -Easy check in -Beautiful small apartment The ACs worked very well and they were needed given the hot and humid weather. The train station is a short walk away and this gives you access to the entire region."
United States
Timothy
The price is AU$358
includes taxes & fees
9 Nov - 10 Nov
Off The Beaten Path - Choose This Private Gem
A spacious hotel lobby with a reception desk, a sofa, a coffee table, and a chandelier.

12. 1 Queen Bed|Nsmk,Kitchen,Sofa-Bed

1 Queen Bed|Nsmk,Kitchen,Sofa-Bed
Malvern PA
8.8 out of 10, Excellent, (3 reviews)
"Microwave and fridge were small but helpful details I noticed immediately on arrival."
United States
Anonymous traveller
The price is AU$157
includes taxes & fees
18 Nov - 19 Nov
1 Queen Bed|Nsmk,Kitchen,Sofa-Bed
A dining area with a white table, wicker chairs, a ceiling fan, and wall-mounted light fixtures.

13. SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome

SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome
Kennett Square
10.0 out of 10, Exceptional, (8 reviews)
"The home was very clean and perfectly situated for easy access to downtown and local sites."
United States
Patricia Nora R.
The price is AU$595
includes taxes & fees
12 Nov - 13 Nov
SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome
A modern kitchen with a central island, bar stools, and a view of the dining area.

14. Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens

Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens
Kennett Square
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, peaceful spot perfect for 1-2 guests. The hosts were great at communicating and the price was very reasonable!"
United States
Sarah S.
The price is AU$448
includes taxes & fees
10 Nov - 11 Nov
Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

15. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.0 out of 10, Wonderful, (4 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
The price is AU$277
includes taxes & fees
16 Nov - 17 Nov
Amish Countryside Escape at Forest Edge Farm
A two-story house with a porch, a swing chair, and a garden.

16. Historic Farmhouse in Chester County

Historic Farmhouse in Chester County
Downingtown
10.0 out of 10, Exceptional, (25 reviews)
"Beds were comfy & location was great!"
United States
Marianne W.
The price is AU$601
includes taxes & fees
10 Nov - 11 Nov
Historic Farmhouse in Chester County
A living room with a flat-screen TV, wooden flooring, a ceiling fan, a sofa, and a window with blinds.

17. Cute 1-Bedroom in Heart of Berwyn

Cute 1-Bedroom in Heart of Berwyn
Berwyn
The price is AU$361
includes taxes & fees
7 Dec - 8 Dec
Cute 1-Bedroom in Heart of Berwyn
A covered porch with stone walls, two wicker chairs, and string lights.

18. Homestead Guesthouse

Homestead Guesthouse
Honey Brook
10.0 out of 10, Exceptional, (44 reviews)
"Definitely will stay again."
United States
robert k.
The price is AU$464
includes taxes & fees
9 Nov - 10 Nov
Homestead Guesthouse
A kitchen shelf with a blue pan, a black pot, a red pot, and a metal colander.

19. Charming 2-bedroom house Phoenixville

Charming 2-bedroom house Phoenixville
Phoenixville
9.4 out of 10, Exceptional, (27 reviews)
"Very clean and good location…short walk from Bridge St. Neva was friendly and communicative. Overall, a great stay!"
United States
Caitlin N.
The price is AU$389
includes taxes & fees
8 Nov - 9 Nov
Charming 2-bedroom house Phoenixville
A modern living room with a herringbone wood wall, a staircase, a sofa, a coffee table, and a bookshelf.

20. Newly built Tiny House in Historic Kennett Square

Newly built Tiny House in Historic Kennett Square
Kennett Square
9.0 out of 10, Wonderful, (4 reviews)
"Home away from home"
United States
Debbie M.
The price is AU$428
includes taxes & fees
9 Nov - 10 Nov
Newly built Tiny House in Historic Kennett Square
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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Find holiday rentals that suit your style

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Top Chester County Hotel Reviews

A spacious lobby with a reception desk, large windows, and a mural of workers.
AmishView Inn and Suites

AmishView Inn and Suites

AmishView Inn and Suites
Ronks

10/10 Excellent

Great way to experience the Amish country
Australia
Terry
Reviewed February 9, 2025
AmishView Inn and Suites

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 favourite 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 depend 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 chosen for you start as low as AU$157 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.