A covered bridge with a sign indicating a 10-foot clearance.

Holiday Homes in Chester Springs

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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
"We loved our stay! Such a warm, welcoming retreat in a beautiful setting with lots of special touches included. They thought of everything! Hope we are able return some day."
United States
Joanne O.
The price is AU$239
includes taxes & fees
1 Oct - 2 Oct
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
9.2 out of 10, Wonderful, (25 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$399
includes taxes & fees
11 Oct - 12 Oct
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, (22 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$688
includes taxes & fees
6 Oct - 7 Oct
Modern & Cozy 4 bd/3 ba WC convenience!
A modern living room with a green wall, a purple sofa, and a neon sign.

4. Comfort, Fun & Retro Retreat

Comfort, Fun & Retro Retreat
Royersford
8.0 out of 10, Very good, (1 review)
The price is AU$666
includes taxes & fees
30 Sept - 1 Oct
Comfort, Fun & Retro Retreat
A garden area with various potted plants and flowers in front of a building with a black door and windows.

5. Ushmila's Nest- private entrance, bedroom & bathroom

Ushmila's Nest- private entrance, bedroom & bathroom
Wayne
10.0 out of 10, Exceptional, (63 reviews)
"A wonderful little oasis in the bustle of the Main Line. Fantastic stay!"
United States
Craig J.
The price is AU$321
includes taxes & fees
30 Sept - 1 Oct
Ushmila's Nest- private entrance, bedroom & bathroom
A stone frog sculpture in a garden setting with a gravel path, a wooden fence, and houses in the background.

6. Historic Farmhouse in Chester County

Historic Farmhouse in Chester County
Downingtown
10.0 out of 10, Exceptional, (22 reviews)
"Loved the beer on tap!"
United States
Kellie B.
The price is AU$576
includes taxes & fees
30 Sept - 1 Oct
Historic Farmhouse in Chester County
A covered porch made for lounging — enjoy the outdoors, any weather

7. Hill School Sports - Colebrookdale RR Fall Rides

Hill School Sports - Colebrookdale RR Fall Rides
Pottstown
10.0 out of 10, Exceptional, (9 reviews)
"We had a wonderful stay! The home was obviously well cared for and Missie thought of every detail!"
United States
Erin H.
The price is AU$448
includes taxes & fees
28 Oct - 29 Oct
Hill School Sports - Colebrookdale RR Fall Rides
A hotel room with a large bed, a TV on a stand, a desk with a chair, and two doors.

8. Cozy 3-Bedroom in Philly Suburbs Paoli

Cozy 3-Bedroom in Philly Suburbs Paoli
Paoli
10.0 out of 10, Exceptional, (11 reviews)
"Property was great! "
United States
Leevon S.
The price is AU$797
includes taxes & fees
25 Oct - 26 Oct
Cozy 3-Bedroom in Philly Suburbs Paoli
A modern kitchen with a central island, bar stools, wooden cabinets, and a large window.

9. Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
10.0 out of 10, Exceptional, (34 reviews)
"Comfortable, clean, thoughtfully stocked property. We would definitely stay again!"
United States
Amy Y.
The price is AU$413
includes taxes & fees
30 Sept - 1 Oct
Underground Railroad 4 Bedroom Farmhouse
A spacious kitchen with a central island, large windows, and a dining area with a view of the street.

10. Heritage Haven - West Chester Borough

Heritage Haven - West Chester Borough
West Chester
9.2 out of 10, Wonderful, (10 reviews)
"Very clean, and bright. Modern kitchen and bathrooms. Well equipped. Excellent location, Walkable"
United States
joseph k.
Heritage Haven - West Chester Borough
A modern bathroom with a vanity, a coffee maker, and a sign on the counter.

11. Cottage by the Pines

Cottage by the Pines
Parkesburg
9.0 out of 10, Wonderful, (6 reviews)
"My main concern at our stay was the lack of cleanliness of the house overall, the entrance had outside dirt, dry leaves and cobwebs .The kitchen table and chairs still had dirt on them from the previous guests, the microwave and oven were not cleaned either with small crumbs of old food, and lots of finger prints on the doors. The refrigerator had food in it from the previous guests. The bathroom didn’t seem to be well cleaned either which I have notified the owner. The house was cozy."
United States
Diva C.
The price is AU$346
includes taxes & fees
30 Sept - 1 Oct
Cottage by the Pines
A river with a stone embankment and trees, a stone building with windows and a chimney, and a bridge in the background.

12. 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, (213 reviews)
"Just perfect !"
United States
Cloudi
The price is AU$312
includes taxes & fees
1 Oct - 2 Oct
Private Suite w/sitting room in the heart of Brandywine Valley
A modern kitchen with white cabinets, a black countertop, and three teal bar stools.

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

Comfort, Fun, & charming! - 5BR oasis w/ Pool
Coatesville
8.0 out of 10, Very good, (8 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$889
includes taxes & fees
12 Oct - 13 Oct
Comfort, Fun, & charming! - 5BR oasis w/ Pool
A modern kitchen with a central island, bar stools, and a refrigerator.

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

Country Outback Cozy Home *W/Camp Fire Pit*
Parkesburg
9.8 out of 10, Exceptional, (48 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$318
includes taxes & fees
1 Oct - 2 Oct
Country Outback Cozy Home *W/Camp Fire Pit*
A covered porch with stone walls, two wicker chairs, and string lights.

15. Homestead Guesthouse

Homestead Guesthouse
Honey Brook
10.0 out of 10, Exceptional, (40 reviews)
"Definitely will stay again."
United States
robert k.
The price is AU$505
includes taxes & fees
26 Oct - 27 Oct
Homestead Guesthouse
A room with a large framed coastal landscape painting, a woven basket with a plant, and a framed certificate on a black console table.

16. The Travelers Havens

The Travelers Havens
Parkesburg
8.8 out of 10, Excellent, (10 reviews)
"We had a great stay with our two dogs. The house was clean and comfortable. We would definitely stay here again!"
United States
Jen D.
The price is AU$325
includes taxes & fees
4 Oct - 5 Oct
The Travelers Havens
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, (22 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$654
includes taxes & fees
6 Oct - 7 Oct
Kennett Square, Near Longwood Gardens & Downtown
A dining area with a white table, wicker chairs, a ceiling fan, and wall-mounted light fixtures.

18. 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, (7 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$626
includes taxes & fees
12 Oct - 13 Oct
SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome
A modern kitchen with white cabinetry, a marble countertop, and a black ceiling with recessed lighting.

19. Convenience, Space, and Charm!

Convenience, Space, and Charm!
Conshohocken
8.6 out of 10, Excellent, (23 reviews)
"Property owner was very helpful"
United States
Wayne A.
The price is AU$727
includes taxes & fees
21 Oct - 22 Oct
Convenience, Space, and Charm!
A modern kitchen with a black and white herringbone backsplash, stainless steel appliances, and a window with a view.

20. Homey Retreat in Historic Kennett Square!!

Homey Retreat in Historic Kennett Square!!
Kennett Square
10.0 out of 10, Exceptional, (108 reviews)
"The property was wonderful...outdoor seating was a plus...the house was clean and the host was attentive. Close to restaurants, a true gem in Kennett square."
United States
Melissa K.
The price is AU$516
includes taxes & fees
30 Sept - 1 Oct
Homey Retreat 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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Top Chester Springs Hotel Reviews

Doubletree By Hilton Reading

Doubletree By Hilton Reading

8/10 Good
"."
Christopher 1-night trip
Posted less than an hour ago
Doubletree By Hilton Reading

Find out more about Chester Springs

Chester Springs Holiday Homes information

Number of reviews
608
Accommodation
205 Holiday Homes
Lowest Price
AU$239
Highest Price
AU$889