A bridge over a river with a sunset sky.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Chester vacation rentals

Free daily continental breakfast

1. Philadelphia Suites-Extended Stay

Philadelphia Suites-Extended Stay
4.0 star property
Southwest Philadelphia
7.4 out of 10, Good, (1,615 reviews)
"I like the price for what we got, perfect for a family of five."
United States
Christine
The price is ￥15,170
￥17,653 total
includes taxes & fees
Aug 17 - Aug 18
Philadelphia Suites-Extended Stay
House (2 Bedrooms) | Front of property

2. Walkable Neighborhood: Updated Morton Home!

Walkable Neighborhood: Updated Morton Home!
3.0 star property
Morton
10.0 out of 10, Exceptional, (1 review)
"Homey, quiet and perfectly located property. Easy to communicate with John. Will definitely be back!"
United States
KEREN
The price is ￥27,869
￥43,909 total
includes taxes & fees
Aug 13 - Aug 14
Walkable Neighborhood: Updated Morton Home!
Reception

3. 4211 Suites

4211 Suites
4.5 star property
West Philadelphia
9.0 out of 10, Wonderful, (856 reviews)
"Very nice for families"
United States
Maynor
The price is ￥19,520
￥22,715 total
includes taxes & fees
Aug 23 - Aug 24
4211 Suites
A river with a stone embankment and trees, a stone building with windows and a chimney, and a bridge in the background.

4. 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, (211 reviews)
"Just perfect !"
United States
Cloudi
The price is ￥23,091
￥33,845 total
includes taxes & fees
Sep 5 - Sep 6
Private Suite w/sitting room in the heart of Brandywine Valley
Smart TV, fireplace, books

5. Quaint 3rd Floor Loft

Quaint 3rd Floor Loft
Upper Darby
9.4 out of 10, Exceptional, (28 reviews)
"This property was unique, clean, and friendly service."
United States
Lori
The price is ￥18,276
￥27,200 total
includes taxes & fees
Aug 13 - Aug 14
Quaint 3rd Floor Loft
2 bedrooms, desk, iron/ironing board, WiFi

6. New 2/2 Across from Fairmount Park | 10 mins to DT

New 2/2 Across from Fairmount Park | 10 mins to DT
North Philadelphia
9.4 out of 10, Exceptional, (17 reviews)
"My family and I enjoyed our stay and area."
United States
Anthony T.
The price is ￥12,264
￥32,111 total
includes taxes & fees
Aug 13 - Aug 14
New 2/2 Across from Fairmount Park | 10 mins to DT
Interior

7. La Pequeña 1BR apartment in trendy Fishtown with AC, W/D, PrivateDeck, fast WiFi

La Pequeña 1BR apartment in trendy Fishtown with AC, W/D, PrivateDeck, fast WiFi
North Philadelphia
9.4 out of 10, Exceptional, (35 reviews)
"Great location. Functional space. Furniture set up was different than showed and a little wonky. "
United States
Sarah E.
The price is ￥15,768
￥34,995 total
includes taxes & fees
Aug 30 - Aug 31
La Pequeña 1BR apartment in trendy Fishtown with AC, W/D, PrivateDeck, fast WiFi
Property grounds

8. Historic Cottage in West Chester PA - Two miles from town.

Historic Cottage in West Chester PA - Two miles from town.
West Chester
10.0 out of 10, Exceptional, (107 reviews)
"Really nice and friendly host. Very beautiful site."
United States
Rebecca Z.
The price is ￥25,483
￥49,222 total
includes taxes & fees
Aug 16 - Aug 17
Historic Cottage in West Chester PA - Two miles from town.
Exterior detail

9. 2mins DT/Patio+Parking/50” Roku TV/400 Mbps

2mins DT/Patio+Parking/50” Roku TV/400 Mbps
Bryn Mawr
9.8 out of 10, Exceptional, (16 reviews)
"Stay was great "
United States
Melissa M.
The price is ￥26,980
￥52,334 total
includes taxes & fees
Aug 27 - Aug 28
2mins DT/Patio+Parking/50” Roku TV/400 Mbps
Lobby sitting area

10. Sosuite at The Queen - Queen Village

Sosuite at The Queen - Queen Village
2.0 star property
South Philadelphia
7.8 out of 10, Good, (76 reviews)
"Perfect area to explore Philly"
United States
Nathan
The price is ￥10,846
￥12,528 total
includes taxes & fees
Aug 26 - Aug 27
Sosuite at The Queen - Queen Village
Rooftop terrace

11. Sosuite at The Onyx - Museum District

Sosuite at The Onyx - Museum District
4.0 star property
Center City
8.4 out of 10, Very Good, (90 reviews)
"This property was convenient and the customer service was so responsive. Definitely appreciated the proximity to all that we wanted to see. Will stay here again💯"
United States
Llewella
The price is ￥16,915
￥19,537 total
includes taxes & fees
Aug 30 - Aug 31
Sosuite at The Onyx - Museum District
Interior

12. Walk to Stadium Events |Kid Friendly | Game Room

Walk to Stadium Events |Kid Friendly | Game Room
South Philadelphia
10.0 out of 10, Exceptional, (47 reviews)
"Everything perfect, as always!"
United States
Benjamin H.
The price is ￥19,598
￥63,246 total
includes taxes & fees
Aug 25 - Aug 26
Walk to Stadium Events |Kid Friendly | Game Room
Outdoor dining

13. Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
9.8 out of 10, Exceptional, (86 reviews)
"We enjoyed Cozy Cottage and would come back again!"
United States
ken s.
The price is ￥31,854
￥56,254 total
includes taxes & fees
Aug 23 - Aug 24
Cozy Spring House in Gorgeous Chadds Ford!
A room with a brick wall and a large poster of a man holding a guitar. The text "RITTENHOUSE MODERN" is visible on the wall.

14. Rittenhouse Modern

Rittenhouse Modern
Center City
8.6 out of 10, Excellent, (17 reviews)
"Always a comfy place to stay when I am in the city!"
United States
Monica Q.
The price is ￥10,751
￥25,025 total
includes taxes & fees
Aug 23 - Aug 24
Rittenhouse Modern
2 bedrooms, desk, iron/ironing board, WiFi (free)

15. Cozy 2 bdrm Unit/Big Kitchen-2 TV- University City

Cozy 2 bdrm Unit/Big Kitchen-2 TV- University City
West Philadelphia
10.0 out of 10, Exceptional, (33 reviews)
"Our place was clean and bright. The host was very responsive! Loved staying here- great location!"
United States
Margaret T.
The price is ￥20,785
￥46,569 total
includes taxes & fees
Aug 16 - Aug 17
Cozy 2 bdrm Unit/Big Kitchen-2 TV- University City
Coffee/tea maker, fridge, microwave, oven

16. 1BR by Drexel, Zoo, Museums, CHOP, UPenn, Rocky

1BR by Drexel, Zoo, Museums, CHOP, UPenn, Rocky
West Philadelphia
9.8 out of 10, Exceptional, (9 reviews)
"Place was exactly as described and pictured. Felt safe and comfortable throughout our stay. Had everything we needed. "
United States
Jennifer
The price is ￥34,249
￥59,778 total
includes taxes & fees
Aug 15 - Aug 16
1BR by Drexel, Zoo, Museums, CHOP, UPenn, Rocky
Coffee/tea maker, microwave, oven, stovetop

17. 1BR by UPenn, Museums, Zoo, CHOP, Drexel, Rocky

1BR by UPenn, Museums, Zoo, CHOP, Drexel, Rocky
West Philadelphia
10.0 out of 10, Exceptional, (4 reviews)
"The apartment was fantastic! Location was so close to everything. The host was wonderful! At first I thought it was rather expensive but after staying there, I’d probably pay more than I did. Will definitely be staying when visiting Philly again!"
Canada
Angad
The price is ￥12,844
￥34,624 total
includes taxes & fees
Aug 13 - Aug 14
1BR by UPenn, Museums, Zoo, CHOP, Drexel, Rocky
Suite, 2 Queen Beds, Balcony | Living area | Smart TV, streaming services

18. Sosuite at The Loxley - Old City

Sosuite at The Loxley - Old City
4.0 star property
Center City
9.2 out of 10, Wonderful, (110 reviews)
"Great location walkable to many key locations and easy bus access to farther points."
United States
Sierra
The price is ￥17,345
￥20,032 total
includes taxes & fees
Aug 17 - Aug 18
Sosuite at The Loxley - Old City
2 bedrooms, desk, iron/ironing board, WiFi (free)

19. Modern/Luxury 2 bdrm- KING Bed- University City

Modern/Luxury 2 bdrm- KING Bed- University City
West Philadelphia
10.0 out of 10, Exceptional, (41 reviews)
"The place is very clean and comfortable. The property is in a residential area and felt safe. It is a 3rd floor apartment with a lot of steps take that into consideration if mobility is an issue. We wish it would have had some living room space which would have been an issue if staying longer or spending more time in the unit but wasnt an issue for our stay this time. Bedrooms were very clean, nicely decorated and comfortable. A nice touch with coffee and a Keurig available. Thank you for a...
United States
Kristen R.
The price is ￥21,071
￥46,898 total
includes taxes & fees
Aug 17 - Aug 18
Modern/Luxury 2 bdrm- KING Bed- University City
Private kitchen

20. NEW 2B Duplex near Sport Complex & Airport Unit-A

NEW 2B Duplex near Sport Complex & Airport Unit-A
South Philadelphia
2.0 out of 10, (1 review)
"Property is listed as new, its anything but that. Everything is from scratch and dent places,bedding was so nasty and contacted host, who told me to contact vrbo. That was a disaster, they gave us back 65 cleaning fee. Wasn't even a place to wash the bed sheets at. Save your money and book a nicer place. Don't even get me started on the parking situation in this area, drive around for an hour before we could find a spot to park. Bedroom doors dont shut or lock, my kids put a chair and broom up...
United States
Adam C.
The price is ￥14,333
￥32,260 total
includes taxes & fees
Sep 10 - Sep 11
NEW 2B Duplex near Sport Complex & Airport Unit-A
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 Hotel Reviews

The Windsor Suites

The Windsor Suites

10/10 Excellent
"Very clean facility with helpful staff. WiFi is the only downside."
Timothy 3-night trip
Posted 1 hour ago
The Windsor Suites

Find out more about Chester

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

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

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

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, we offer vacation rentals in Chester close to Camp Upland, or you can choose a secluded option if you'd like a relaxing place to stay. Our travelers say Chester has a good selection of restaurants. Make sure you have time to check out the soccer matches and university setting during your trip.

What's the top vacation rental that Chester has to offer?

South Philly Terrace: This vacation home near Chester is located near the airport and offers a rooftop terrace, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Chester?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Chester stay.

What can I see and do in Chester?

Ethel Waters Park and Crozier Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Camp Upland. In the larger area, you’ll find popular places like Xfinity Mobile Arena and Lincoln Financial Field.

What are vacation rentals like in Chester?

Vacation rentals are private properties you can reserve for several days or longer in Chester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family getaway.