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Holiday Homes in Downingtown

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Downingtown 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 AU$241
includes taxes & fees
6 Oct - 7 Oct
Spacious 1-bedroom suite surrounded by nature in charming Downingtown.
A stone frog sculpture in a garden setting with a gravel path, a wooden fence, and houses in the background.

2. 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$582
includes taxes & fees
6 Oct - 7 Oct
Historic Farmhouse in Chester County
A modern kitchen with a central island, bar stools, wooden cabinets, and a large window.

3. 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$417
includes taxes & fees
7 Oct - 8 Oct
Underground Railroad 4 Bedroom Farmhouse
A modern kitchen with white cabinets, a black countertop, and three teal bar stools.

4. 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$898
includes taxes & fees
12 Oct - 13 Oct
Comfort, Fun, & charming! - 5BR oasis w/ Pool
A modern kitchen with white cabinets, a black stove, and a black dishwasher.

5. 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$662
includes taxes & fees
6 Oct - 7 Oct
Modern & Cozy 4 bd/3 ba WC convenience!
A rustic barn interior with wooden beams, a large window, and string lights.

6. Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (43 reviews)
"Very cool place! "
United States
Scott M.
The price is AU$451
includes taxes & fees
2 Nov - 3 Nov
Underground Railroad Barn
A modern kitchen with a central island, bar stools, and a refrigerator.

7. 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$316
includes taxes & fees
6 Oct - 7 Oct
Country Outback Cozy Home *W/Camp Fire Pit*
A room with a large framed coastal landscape painting, a woven basket with a plant, and a framed certificate on a black console table.

8. The Travelers Havens

The Travelers Havens
Parkesburg
8.8 out of 10, Excellent, (11 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$332
includes taxes & fees
7 Oct - 8 Oct
The Travelers Havens
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

9. 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$652
includes taxes & fees
26 Oct - 27 Oct
Kennett Square, Near Longwood Gardens & Downtown
A modern bathroom with a vanity, a coffee maker, and a sign on the counter.

10. Cottage by the Pines

Cottage by the Pines
Parkesburg
9.0 out of 10, Wonderful, (6 reviews)
"We enjoyed our stay at the cottage. Wawa is 2 min away as is cvs for any needs."
United States
Ron F.
The price is AU$349
includes taxes & fees
6 Oct - 7 Oct
Cottage by the Pines
A covered porch with stone walls, two wicker chairs, and string lights.

11. 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$510
includes taxes & fees
26 Oct - 27 Oct
Homestead Guesthouse
A dining area with a white table, wicker chairs, a ceiling fan, and wall-mounted light fixtures.

12. 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$631
includes taxes & fees
12 Oct - 13 Oct
SquareHaus - At the heart of Kennett Sq - 3-bedroom townhome
A river with a stone embankment and trees, a stone building with windows and a chimney, and a bridge in the background.

13. 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, (214 reviews)
"Just perfect !"
United States
Cloudi
The price is AU$316
includes taxes & fees
6 Oct - 7 Oct
Private Suite w/sitting room in the heart of Brandywine Valley
A wooden staircase leading to a white door with a 'HELLO' mat.

14. Charming 2-bedroom house Phoenixville

Charming 2-bedroom house Phoenixville
Phoenixville
9.4 out of 10, Exceptional, (26 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$404
includes taxes & fees
11 Oct - 12 Oct
Charming 2-bedroom house Phoenixville
A modern kitchen with a black and white herringbone backsplash, stainless steel appliances, and a window with a view.

15. 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$567
includes taxes & fees
14 Oct - 15 Oct
Homey Retreat in Historic Kennett Square!!
A cozy living room with a fireplace, a sofa set, and a coffee table.

16. Cozy hideaway on your own corner of our homestead

Cozy hideaway on your own corner of our homestead
Reinholds
9.8 out of 10, Exceptional, (156 reviews)
"Wonderful stay! "
United States
Adam V.
The price is AU$239
includes taxes & fees
6 Oct - 7 Oct
Cozy hideaway on your own corner of our homestead
A spacious living room with a large bed, seating area, and a fireplace.

17. Spacious 3BR Historic Home | Walk Downtown+Parking

Spacious 3BR Historic Home | Walk Downtown+Parking
Kennett Square
10.0 out of 10, Exceptional, (45 reviews)
"We greatly enjoyed our stay at this beautiful house, in a perfect location. It was close to all the shops and restaurants and had a beautiful peaceful garden. Would happily stay again in the future!"
United States
Marta R.
The price is AU$1,171
includes taxes & fees
6 Oct - 7 Oct
Spacious 3BR Historic Home | Walk Downtown+Parking
A hotel room with a large bed, a TV on a stand, a desk with a chair, and two doors.

18. 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$814
includes taxes & fees
25 Oct - 26 Oct
Cozy 3-Bedroom in Philly Suburbs Paoli
A cozy living room with a rustic brick wall, two armchairs, a tufted ottoman, and a chandelier.

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

Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens
Chadds Ford
9.8 out of 10, Exceptional, (54 reviews)
"Beautiful property for a group weekend!"
United States
Lillian E.
The price is AU$2,420
includes taxes & fees
6 Oct - 7 Oct
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens
A garden with a fountain, surrounded by lush greenery and flowering plants.

20. New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (29 reviews)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is AU$263
includes taxes & fees
19 Oct - 20 Oct
New Construction townhome close to everything downtown w/transparent pricing
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 Downingtown Hotel Reviews

Red Caboose Motel

Red Caboose Motel

10/10 Excellent
"its about 10stars for kids and 3-4 stars for adults. Its amazing for kids. I had grandkids with me agees from 2 to 9. They love it!!! LOVE IT!! Sleep in the train?? can not be any better for them. Everything is small but very cozy( its like in a real train car).they enjoyed every minutes and i was very happy. Very convenient locations to all attraction."Cherry crest farm" basically right around the corner. We spent the entire day there. And around 8:30 pm it was a beautiful firework at the farm and we saw it from our hotel window. Everything is very close. Kids can not stop talking about this weekend."
Irina 2-night trip
Posted less than an hour ago
Red Caboose Motel

Find out more about Downingtown

Downingtown Holiday Homes information

Number of reviews
907
Accommodation
302 Holiday Homes
Lowest Price
AU$239
Highest Price
AU$2,420