A bridge over a river with a sunset sky.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chester vacation rentals

House (2 Bedrooms) | Front of property

1. 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
$248 nightly
The price is $276
Aug 20 - Aug 21
Total with taxes and fees
Walkable Neighborhood: Updated Morton Home!
Free daily continental breakfast

2. Philadelphia Suites-Extended Stay

Philadelphia Suites-Extended Stay
4.0 star property
Southwest Philadelphia
7.4 out of 10, Good, (1,628 reviews)
"The stay was great and the room was clean !"
United States
Askin
$79 nightly
The price is $92
Aug 27 - Aug 28
Total with taxes and fees
Philadelphia Suites-Extended Stay
Exterior

3. Tudor Place

Tudor Place
4.0 star property
Lansdowne
$2,174 nightly
The price is $2,413
Aug 24 - Aug 25
Total with taxes and fees
Tudor Place
Outdoor dining

4. Book Now! Guests' Favorite, King Bed, Sleeps 12

Book Now! Guests' Favorite, King Bed, Sleeps 12
East Lansdowne
9.6 out of 10, Exceptional, (59 reviews)
"This is my second time staying @ this property . The house is beautiful the back yard is amazing. I will definitely be booking again & again. "
United States
Monique M.
$632 nightly
The price is $698
Aug 31 - Sep 1
Total with taxes and fees
Book Now! Guests' Favorite, King Bed, Sleeps 12
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
$155 nightly
The price is $171
Aug 23 - Aug 24
Total with taxes and fees
Quaint 3rd Floor Loft
A river with a stone embankment and trees, a stone building with windows and a chimney, and a bridge in the background.

6. 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
$195 nightly
The price is $200
Sep 1 - Sep 2
Total with taxes and fees
Private Suite w/sitting room in the heart of Brandywine Valley
Dining

7. Spacious & Cozy with luxury furnitures /1 King+2 Queen/-University City

Spacious & Cozy with luxury furnitures /1 King+2 Queen/-University City
West Philadelphia
10.0 out of 10, Exceptional, (25 reviews)
"The location was perfect for visiting family. "
United States
Susan H.
$309 nightly
The price is $354
Aug 20 - Aug 21
Total with taxes and fees
Spacious & Cozy with luxury furnitures /1 King+2 Queen/-University City
2 bedrooms, desk, iron/ironing board, WiFi (free)

8. 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)
"Fabulous property with thoughtful amenities. Would stay here again in a heartbeat."
United States
Rebecca S.
$257 nightly
The price is $294
Aug 23 - Aug 24
Total with taxes and fees
Modern/Luxury 2 bdrm- KING Bed- University City
2 bedrooms, desk, iron/ironing board, WiFi (free)

9. 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.
$256 nightly
The price is $292
Aug 30 - Aug 31
Total with taxes and fees
Cozy 2 bdrm Unit/Big Kitchen-2 TV- University City
Outdoor dining

10. 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.
$320 nightly
The price is $353
Aug 23 - Aug 24
Total with taxes and fees
Cozy Spring House in Gorgeous Chadds Ford!
Interior

11. Luxury 4 Bedroom Apartment in Philadelphia

Luxury 4 Bedroom Apartment in Philadelphia
South Philadelphia
6.8 out of 10, (12 reviews)
"Great setting to lounge around at"
United States
Dewanne F.
$393 nightly
The price is $450
Aug 24 - Aug 25
Total with taxes and fees
Luxury 4 Bedroom Apartment in Philadelphia
Reception

12. 4211 Suites

4211 Suites
4.5 star property
West Philadelphia
9.0 out of 10, Wonderful, (867 reviews)
"Staff was great and the place was clean."
United States
Erica
$120 nightly
The price is $140
Aug 31 - Sep 1
Total with taxes and fees
4211 Suites
Property grounds

13. Hidden Gem Townhome with 2 BRs -University City -near UPenn&Drexel

Hidden Gem Townhome with 2 BRs -University City -near UPenn&Drexel
West Philadelphia
10.0 out of 10, Exceptional, (34 reviews)
"It truly is a hidden gem. Thanks for a wonderful stay"
United States
Danny P.
$287 nightly
The price is $328
Aug 23 - Aug 24
Total with taxes and fees
Hidden Gem Townhome with 2 BRs -University City -near UPenn&Drexel
Smart TV, books, stereo

14. Cozy and Clean home Conveniently located in South Phila.

Cozy and Clean home Conveniently located in South Phila.
South Philadelphia
9.4 out of 10, Exceptional, (53 reviews)
"Denise was super tentive to me. Check in was easy. Denise left snacks for us. I enjoyed the stay and the house was extremely cozy. I rate this place a 10! Definitely look forward to returning."
United States
Stephanie B.
$369 nightly
The price is $422
Sep 7 - Sep 8
Total with taxes and fees
Cozy and Clean home Conveniently located in South Phila.
Interior

15. 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.
$343 nightly
The price is $392
Aug 25 - Aug 26
Total with taxes and fees
Walk to Stadium Events |Kid Friendly | Game Room
Smart TV

16. Executive 3BR University City within minutes to Drexel Penn CHOP

Executive 3BR University City within minutes to Drexel Penn CHOP
West Philadelphia
$513 nightly
The price is $587
Sep 1 - Sep 2
Total with taxes and fees
Executive 3BR University City within minutes to Drexel Penn CHOP
Jetted tub

17. Cozy Home near City Center with Hot tub

Cozy Home near City Center with Hot tub
3.0 star property
South Philadelphia
10.0 out of 10, Exceptional, (3 reviews)
"The place was nice and clean and the host was very accommodating."
United States
DaRon
$2,122 nightly
The price is $2,415
Sep 15 - Sep 16
Total with taxes and fees
Cozy Home near City Center with Hot tub
Private kitchen

18. 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.
$176 nightly
The price is $202
Aug 20 - Aug 21
Total with taxes and fees
NEW 2B Duplex near Sport Complex & Airport Unit-A
Smart TV

19. 2-bedroom Rowhome w/ AC in South Philly 10 min to Plane/Train & 5 min to Stadium

2-bedroom Rowhome w/ AC in South Philly 10 min to Plane/Train & 5 min to Stadium
South Philadelphia
$206 nightly
The price is $236
Aug 23 - Aug 24
Total with taxes and fees
2-bedroom Rowhome w/ AC in South Philly 10 min to Plane/Train & 5 min to Stadium
Exterior

20. Beautiful 1BD Apt with Roofdeck in Passyunk Square

Beautiful 1BD Apt with Roofdeck in Passyunk Square
South Philadelphia
9.6 out of 10, Exceptional, (16 reviews)
"Apartment was clean and in a great location. The stairs were the only downfall overall but not such an issue that I wouldn’t recommend. Enjoy our stay here and would stay again."
United States
Rachelle K.
$226 nightly
The price is $259
Aug 24 - Aug 25
Total with taxes and fees
Beautiful 1BD Apt with Roofdeck in Passyunk 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 Hotel Reviews

Motto by Hilton Philadelphia Rittenhouse Square

Motto by Hilton Philadelphia Rittenhouse Square

10/10 Excellent
"Very stylish and welcoming hotel, cool vibe - greeted genuinely at the entrance, efficient low key professional front desk check in staff, very clean modern comfortable room w a good tv, nice extras w the bath @products, for the $$ its a terrific place. A super convenient location for travelers like me who like all sorts of dining options, access to public transportation, shopping from great shoe stores to Target and CVS a stones throw away. On site independently run restaurant bar and coffee place buzzing in a good energy low key way. The bathroom in queen room room had a frosted glass door adjacent to very comfy bed, nicely appointed room w large step in shower but not a lot of privacy."
Sharon 1-night trip
Posted less than an hour ago
Motto by Hilton Philadelphia Rittenhouse Square

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Fantastic 4BR Townhouse W/ HOTTUB: This vacation home rental near Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.