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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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, (1 review)
"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 NZ$279
includes taxes & fees
9 Nov - 10 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 NZ$485
includes taxes & fees
7 Nov - 8 Nov
Charming 2-bedroom house Phoenixville
A spacious kitchen with white cabinetry, a black refrigerator, and a wooden floor.

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, (23 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 NZ$770
includes taxes & fees
1 Nov - 2 Nov
Modern & Cozy 4 bd/3 ba WC convenience!
A hotel room with a large bed, a TV on a stand, a desk with a chair, and two doors.

4. 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 NZ$861
includes taxes & fees
3 Nov - 4 Nov
Cozy 3-Bedroom in Philly Suburbs Paoli
A kitchen with a coffee maker, a sign that says "COFFEE TIME", and a heart-shaped decoration on the counter.

5. Comfort, Fun & Retro Retreat

Comfort, Fun & Retro Retreat
Royersford
8.0 out of 10, Very good, (1 review)
The price is NZ$796
includes taxes & fees
1 Nov - 2 Nov
Comfort, Fun & Retro Retreat
A living room with a flat-screen TV, wooden flooring, a ceiling fan, a sofa, and a window with blinds.

6. Cute 1-Bedroom in Heart of Berwyn

Cute 1-Bedroom in Heart of Berwyn
Berwyn
The price is NZ$452
includes taxes & fees
11 Nov - 12 Nov
Cute 1-Bedroom in Heart of Berwyn
A modern living room with two leather armchairs, a glass coffee table, and a dining area with a wooden floor and white walls.

7. 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 NZ$959
includes taxes & fees
24 Nov - 25 Nov
Riverfront Retreat - Convenience + Kayaks - 3 bed 2 ba
A two-story house with a porch, a swing chair, and a garden.

8. Historic Farmhouse in Chester County

Historic Farmhouse in Chester County
Downingtown
10.0 out of 10, Exceptional, (23 reviews)
"Beds were comfy & location was great!"
United States
Marianne W.
The price is NZ$768
includes taxes & fees
1 Nov - 2 Nov
Historic Farmhouse in Chester County
A covered porch made for lounging — enjoy the outdoors, any weather

9. 7 Min to Hill School Squash Tourney | Modern Stay

7 Min to Hill School Squash Tourney | Modern Stay
Pottstown
10.0 out of 10, Exceptional, (10 reviews)
"The bed was comfortable and the backyard was large. We enjoyed sitting on the back patio. It is very clean and has all the amenities needed. We had our dog with us so having the large yard was especially nice. The owner is very nice and friendly."
United States
Donna
The price is NZ$538
includes taxes & fees
4 Nov - 5 Nov
7 Min to Hill School Squash Tourney | Modern Stay
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
9.4 out of 10, Exceptional, (11 reviews)
"Very clean, and bright. Modern kitchen and bathrooms. Well equipped. Excellent location, Walkable"
United States
joseph k.
The price is NZ$979
includes taxes & fees
1 Nov - 2 Nov
Heritage Haven - West Chester Borough
A covered patio area with a wooden bench, a small bar area, and a staircase leading to an upper level.

11. Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (45 reviews)
"Very cool place! "
United States
Scott M.
The price is NZ$545
includes taxes & fees
4 Nov - 5 Nov
Underground Railroad Barn
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, (43 reviews)
"Homestead Vacation Home is a clean, comfortable and spacious house in a peaceful and private setting. With all of the basics, in addition to many extras, this place truly feels like home while being on vacation. The location is ideal as it’s situated in a rural setting yet close to many area attractions. This was our second time staying here and we would love to return again next year!"
United States
Jenny K.
The price is NZ$574
includes taxes & fees
9 Nov - 10 Nov
Homestead Guesthouse
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 NZ$1,082
includes taxes & fees
1 Nov - 2 Nov
Comfort, Fun, & charming! - 5BR oasis w/ Pool
A modern kitchen with a central island, bar stools, wooden cabinets, and a large window.

14. 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 NZ$600
includes taxes & fees
5 Nov - 6 Nov
Underground Railroad 4 Bedroom Farmhouse
A river with a stone embankment and trees, a stone building with windows and a chimney, and a bridge in the background.

15. 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 NZ$362
includes taxes & fees
3 Nov - 4 Nov
Private Suite w/sitting room in the heart of Brandywine Valley
A modern interior with a sofa, a coffee table, and a kitchen area with a dining set.

16. 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 NZ$371
includes taxes & fees
2 Nov - 3 Nov
Country Outback Cozy Home *W/Camp Fire Pit*
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
8.4 out of 10, Very good, (25 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 NZ$773
includes taxes & fees
9 Nov - 10 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 NZ$487
includes taxes & fees
2 Nov - 3 Nov
Charming 5 Bedroom Fully Renovated Historic Home
An aerial view of a property with a pond, dense forest, and a red building with a large window.

19. Cedar Glen Farmhouse • 1800s Stone Retreat

Cedar Glen Farmhouse • 1800s Stone Retreat
Mohnton
10.0 out of 10, Exceptional, (8 reviews)
"Hosts were very friendly and helpful ..house had character and charm and was original with Very thick soundproof walls and yet warm and inviting. Would recommend this home to anyone wanting privacy and seclusion in a safe neighborgood."
United States
sam p.
The price is NZ$771
includes taxes & fees
5 Nov - 6 Nov
Cedar Glen Farmhouse • 1800s Stone Retreat
A dining area with a white table, wicker chairs, a ceiling fan, and wall-mounted light fixtures.

20. 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 NZ$736
includes taxes & fees
9 Nov - 10 Nov
SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome
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

The Golfers Inn

The Golfers Inn

10/10 Excellent
"Good got the job done!"
Mason 1-night trip
Posted 1 hour ago
The Golfers Inn

Find out more about Chester Springs

Chester Springs Holiday Homes information

Number of reviews
535
Accommodation
209 Holiday Homes
Lowest Price
NZ$279
Highest Price
NZ$1,082