Holiday Homes in Chester Springs

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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Chester Springs holiday homes

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$231
includes taxes & fees
29 Nov - 30 Nov
Spacious 1-bedroom suite surrounded by nature in charming Downingtown.
A wooden staircase leading to a white door with a 'HELLO' mat.

2. 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$402
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom house Phoenixville
A street with outdoor seating at a restaurant named "Sterling Brewery."

3. Modern & Cozy 4 bd/3 ba WC convenience!

Modern & Cozy 4 bd/3 ba WC convenience!
West Chester
9.0 out of 10, Wonderful, (24 reviews)
"Lovely house in West Chester, we used it for a long weekend with family doing touristy things in Philadelphia, it was nice to be able to get out of the city in the evenings."
United States
Kevin M.
The price is AU$780
includes taxes & fees
16 Nov - 17 Nov
Modern & Cozy 4 bd/3 ba WC convenience!
A hallway with wooden flooring, a desk with a chair, and two doors leading to other rooms.

4. Cute 1-Bedroom in Heart of Berwyn

Cute 1-Bedroom in Heart of Berwyn
Berwyn
The price is AU$363
includes taxes & fees
7 Dec - 8 Dec
Cute 1-Bedroom in Heart of Berwyn
A hallway with a carpeted floor leading to a staircase with stone steps and white walls.

5. Comfort, Fun & Retro Retreat

Comfort, Fun & Retro Retreat
Royersford
8.0 out of 10, Very good, (1 review)
The price is AU$675
includes taxes & fees
23 Nov - 24 Nov
Comfort, Fun & Retro Retreat
A red Adirondack chair by a pond surrounded by dense trees.

6. Riverfront Retreat - Convenience + Kayaks - 3 bed 2 ba

Riverfront Retreat - Convenience + Kayaks - 3 bed 2 ba
Downingtown
10.0 out of 10, Exceptional, (4 reviews)
"The stay was great. Perfect location for our needs. Would definitely stay again"
United States
Shaun H.
The price is AU$812
includes taxes & fees
17 Nov - 18 Nov
Riverfront Retreat - Convenience + Kayaks - 3 bed 2 ba
A hotel room with a large bed, a TV on a stand, a desk with a chair, and two doors.

7. Cozy 3-Bedroom in Philly Suburbs Paoli

Cozy 3-Bedroom in Philly Suburbs Paoli
Paoli
10.0 out of 10, Exceptional, (12 reviews)
"Property was great! "
United States
Leevon S.
The price is AU$772
includes taxes & fees
16 Nov - 17 Nov
Cozy 3-Bedroom in Philly Suburbs Paoli
A stone frog sculpture in a garden setting with a gravel path, a wooden fence, and houses in the background.

8. 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$615
includes taxes & fees
16 Nov - 17 Nov
Historic Farmhouse in Chester County
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island.

9. Heritage Haven - West Chester Borough

Heritage Haven - West Chester Borough
West Chester
9.4 out of 10, Exceptional, (13 reviews)
"Very clean, and bright. Modern kitchen and bathrooms. Well equipped. Excellent location, Walkable"
United States
joseph k.
The price is AU$795
includes taxes & fees
16 Nov - 17 Nov
Heritage Haven - West Chester Borough
A rustic barn interior with wooden beams, a large window, and string lights.

10. 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$445
includes taxes & fees
16 Nov - 17 Nov
Underground Railroad Barn
A patio with a grill, outdoor table and chairs, and a stone wall.

11. Cozy 2-bedroom house in tranquil Schwenksville with AC

Cozy 2-bedroom house in tranquil Schwenksville with AC
Schwenksville
The price is AU$368
includes taxes & fees
17 Nov - 18 Nov
Cozy 2-bedroom house in tranquil Schwenksville with AC
A covered porch with stone walls, two wicker chairs, and string lights.

12. 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$445
includes taxes & fees
17 Nov - 18 Nov
Homestead Guesthouse
A rustic barn interior with wooden beams, a large arched window, and string lights.

13. 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$490
includes taxes & fees
16 Nov - 17 Nov
Underground Railroad 4 Bedroom Farmhouse
A hallway with a blue wall covered in foliage and a neon sign that reads "Don't Worry Be Happy."

14. Comfort, Fun, & charming! - 5BR oasis w/ Pool

Comfort, Fun, & charming! - 5BR oasis w/ Pool
Coatesville
8.0 out of 10, Very good, (9 reviews)
"This is a fantastic property in a gorgeous area. Room for a big crowd yet it feels quite cozy. The host David attended to our every need and request. He was really responsive and treated us like royalty. The pool is absolutely divine. We will definitely stay here again."
United States
Jennifer W.
The price is AU$937
includes taxes & fees
18 Nov - 19 Nov
Comfort, Fun, & charming! - 5BR oasis w/ Pool
A stable with a horse, surrounded by trees and a wooden fence.

15. 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$311
includes taxes & fees
30 Nov - 1 Dec
Country Outback Cozy Home *W/Camp Fire Pit*
A garden with tall blue flowers, red foliage, and a glass structure in the background.

16. Private Suite w/sitting room in the heart of Brandywine Valley

Private Suite w/sitting room in the heart of Brandywine Valley
Wilmington
10.0 out of 10, Exceptional, (215 reviews)
"An outstanding rental, we stayed six nights and loved the location. Had a lovely pond next door with walking/running path."
United States
Melissa
The price is AU$312
includes taxes & fees
15 Nov - 16 Nov
Private Suite w/sitting room in the heart of Brandywine Valley
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

17. Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.6 out of 10, Excellent, (28 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$632
includes taxes & fees
17 Nov - 18 Nov
Kennett Square, Near Longwood Gardens & Downtown
A modern kitchen with white cabinetry, a central island with a sink, and stainless steel appliances.

18. Charming 5 Bedroom Fully Renovated Historic Home

Charming 5 Bedroom Fully Renovated Historic Home
Reading
10.0 out of 10, Exceptional, (11 reviews)
"Nicely renovated, great stay"
United States
Bill H.
The price is AU$418
includes taxes & fees
17 Nov - 18 Nov
Charming 5 Bedroom Fully Renovated Historic Home
A dining area with a white table, wicker chairs, a ceiling fan, and wall-mounted light fixtures.

19. 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, (9 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$633
includes taxes & fees
2 Dec - 3 Dec
SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome
An outdoor seating area with wooden tables and chairs, a central bar area, and a pergola structure.

20. Convenience, Space, and Charm!

Convenience, Space, and Charm!
Conshohocken
8.8 out of 10, Excellent, (23 reviews)
"Very close to the main street of Conshohoken so you can easily walk to a restaurant for coffee, lunch or dinner."
United States
Debra G.
The price is AU$717
includes taxes & fees
23 Nov - 24 Nov
Convenience, Space, and Charm!
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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Learn more about Chester Springs

Historic farmhouses and rolling hills define this charming town where you can explore the Yellow Springs village ruins. Visit Marsh Creek State Park for boating and fishing, or catch a performance at the People's Light theatre in nearby Malvern.

See all hotels in Chester Springs
A covered bridge with a sign indicating a 10-foot clearance.

Top reviews in Chester Springs

A hotel lobby with a sofa, two patterned armchairs, a coffee table, a kitchen area, and a framed artwork on the wall.
Hampton Inn Downingtown/Exton

Hampton Inn Downingtown/Exton

Hampton Inn Downingtown/Exton
Exton

8/10 Good

The room was very clean.Staff was vey friendly.
Australia
Kenneth
Reviewed September 3, 2026
Hampton Inn Downingtown/Exton