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Downingtown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Downingtown vacation 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
"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 ￥14,155
￥26,030 total
includes taxes & fees
Sep 29 - Sep 30
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 ￥29,097
￥61,113 total
includes taxes & fees
Sep 29 - Sep 30
Historic Farmhouse in Chester County
A dock with colorful kayaks and a sailboat, a sign indicating 'Lifeguards on Duty', and a calm lake with a forested shoreline.

3. Quiet Cottage In The Woods with Hot Tub

Quiet Cottage In The Woods with Hot Tub
Glenmoore
9.6 out of 10, Exceptional, (15 reviews)
"This was a great stay and Dave was super responsive as we added an extra night. Would highly recommend! "
United States
Nicole L.
The price is ￥37,197
￥65,737 total
includes taxes & fees
Sep 29 - Sep 30
Quiet Cottage In The Woods with Hot Tub
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 ￥41,758
￥94,793 total
includes taxes & fees
Oct 18 - Oct 19
Comfort, Fun, & charming! - 5BR oasis w/ Pool
A street with outdoor seating at a restaurant named "Sterling Brewery."

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 ￥34,149
￥72,087 total
includes taxes & fees
Oct 6 - Oct 7
Modern & Cozy 4 bd/3 ba WC convenience!
A modern kitchen with a central island, bar stools, wooden cabinets, and a large window.

6. 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 ￥15,571
￥43,639 total
includes taxes & fees
Sep 29 - Sep 30
Underground Railroad 4 Bedroom Farmhouse
A room with a large framed coastal landscape painting, a woven basket with a plant, and a framed certificate on a black console table.

7. 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 ￥17,144
￥34,758 total
includes taxes & fees
Oct 4 - Oct 5
The Travelers Havens
A rustic barn interior with wooden beams, a large window, and string lights.

8. Underground Railroad Barn

Underground Railroad Barn
Kennett Square
10.0 out of 10, Exceptional, (42 reviews)
"Very cool place! "
United States
Scott M.
The price is ￥19,660
￥48,279 total
includes taxes & fees
Oct 21 - Oct 22
Underground Railroad Barn
A covered deck with outdoor furniture, a white fence, and a view of a green landscape.

9. 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, (198 reviews)
"Great place to stay in a great location! It was clean and very comfortable."
United States
Mark C.
The price is ￥18,402
￥36,854 total
includes taxes & fees
Sep 29 - Sep 30
Black Horse - FarmGuest House A Travelers Rest and a Vacationers Haven
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)
"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 ￥20,572
￥37,179 total
includes taxes & fees
Sep 29 - Sep 30
Cottage by the Pines
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

11. 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 ￥19,188
￥68,945 total
includes taxes & fees
Sep 29 - Sep 30
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.

12. 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, (103 reviews)
"Apartment had everything we needed for our stay. Very welcoming and beautiful home. Close enough to everything, yet secluded enough to enjoy the quiet. The eggs, milk, bread and jelly were amazing. Cant wait to come back. "
United States
Patrick W.
The price is ￥25,951
￥45,932 total
includes taxes & fees
Sep 29 - Sep 30
Solid Rock Homestead Guest House. On the Farm. Enjoy the Animals!
A modern living room with two grey sofas, a small side table, a fireplace, and a view of the outdoors.

13. King Bed, Cozy Patio Fire-Pit Area

King Bed, Cozy Patio Fire-Pit Area
Parkesburg
9.8 out of 10, Exceptional, (27 reviews)
"It was just as beautiful as the pictures show. We loved our stay and would stay there again!"
United States
Laura Q.
The price is ￥13,576
￥31,498 total
includes taxes & fees
Sep 30 - Oct 1
King Bed, Cozy Patio Fire-Pit Area
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, (9 reviews)
"It was everything we hoped it would be"
United States
Carla H.
The price is ￥27,653
￥50,614 total
includes taxes & fees
Sep 29 - Sep 30
Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens
A spacious kitchen with a central island, large windows, and a dining area with a view of the street.

15. 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.
The price is ￥46,280
￥86,051 total
includes taxes & fees
Sep 29 - Sep 30
Heritage Haven - West Chester Borough
A wooden pathway leading to a house with a deck.

16. Peaceful, country setting on Fountain Hill Farm

Peaceful, country setting on Fountain Hill Farm
Gap
10.0 out of 10, Exceptional, (261 reviews)
"Absolutely charming, relaxing and the owners are so sweet. They had absolutely every comfort of home, even toys for my daughter and milk in the fridge. This has been my favorite stay and I hope to come back with my husband for a longer stay one day !"
United States
Krystyn M.
The price is ￥15,571
￥25,856 total
includes taxes & fees
Sep 30 - Oct 1
Peaceful, country setting on Fountain Hill Farm
A covered porch with stone walls, two wicker chairs, and string lights.

17. 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 ￥25,102
￥52,148 total
includes taxes & fees
Sep 29 - Sep 30
Homestead Guesthouse
A modern kitchen with a central island, bar stools, and a refrigerator.

18. 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 ￥19,345
￥33,689 total
includes taxes & fees
Oct 5 - Oct 6
Country Outback Cozy Home *W/Camp Fire Pit*
A river with a stone embankment and trees, a stone building with windows and a chimney, and a bridge in the background.

19. 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 ￥22,806
￥33,270 total
includes taxes & fees
Oct 1 - Oct 2
Private Suite w/sitting room in the heart of Brandywine Valley
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, (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 ￥26,046
￥68,162 total
includes taxes & fees
Oct 11 - Oct 12
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 Downingtown Hotel Reviews

Best Western Plus Revere Inn & Suites

Best Western Plus Revere Inn & Suites

10/10 Excellent
"We had a great stay. We stay every year for the Sight and Sound show."
Tara 2-night trip
Posted 1 hour ago
Best Western Plus Revere Inn & Suites

Find out more about Downingtown

Search for holiday rentals in Downingtown on Expedia! You can easily find your home rentals, villas, holiday apartments in Downingtown using one of the methods below:

  • View our selection of featured holiday rentals in Downingtown
  • Use the map to find apartments and other holiday homes in the Downingtown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Downingtown while they last

Look no further and take a look at our great range of rental properties in Downingtown!

Frequently asked questions

Can I find a vacation rental in Downingtown?

Yes, we have vacation rentals in Downingtown close to United Sports, or you can go with a more secluded option if you'd like a relaxing place to stay. Downingtown is known for its basketball games and forests.

What are some of the best vacation home rentals that Downingtown has to offer?

Hilltop Haven |Slower Pace, Timeless Views: This vacation home near Downingtown is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Downingtown?

Choose from 6 Expedia vacation rentals in Downingtown for a memorable vacation.

What can I see and do in Downingtown?

Family-friendly attractions include Lloyd Park, whereas Struble Trail Norwood Road Trailhead is a spot to enjoy the outdoors. Other places in town to visit include Victory Brewing Company and Dowington Country Club.

What are vacation rentals like in Downingtown?

Vacation rentals are private properties you can book for a couple days or more in Downingtown. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family gatherings.