Chester Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chester vacation rentals

The Serenity Manor – A Restful Heritage Retreat

The Serenity Manor – A Restful Heritage Retreat
Chester
6.0 out of 10, (1 review)
"Owner gave a pass code to get into the property thru the front door. The same pass code was used to access bedroom doors inside but those locks were troublesome and didn't seem to work as intended. We learned to never close the doors to avoid the issue. In general everything appeared clean. However, our one year old ended up with very black hands and knees after crawling on the floors. Linens and towels were clean and abundant. Bathrooms were new and clean. The posting mentioned AC. We stayed...
United States
Doug S.
$305 nightly
The price is $337
May 12 - May 13
Total with taxes and fees
The Serenity Manor – A Restful Heritage Retreat

The Airport Lodge - 10 mins from Airport

The Airport Lodge - 10 mins from Airport
Collingdale
10.0 out of 10, Exceptional, (10 reviews)
"Very nice accomodations, easy communication. Hope to be back soon!"
United States
Gina
$125 nightly
The price is $138
May 13 - May 14
Total with taxes and fees
The Airport Lodge - 10 mins from Airport

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, (14 reviews)
"Stay was great "
United States
Melissa M.
$259 nightly
The price is $301
May 10 - May 11
Total with taxes and fees
2mins DT/Patio+Parking/50” Roku TV/400 Mbps

Lovely Home Near the Art Museum

Lovely Home Near the Art Museum
North Philadelphia
10.0 out of 10, Exceptional, (25 reviews)
"We stayed here so we could be close to art museum and this was perfect! There was four of us and had plenty of beds and amenities!! Would stay again"
United States
Amy N.
$268 nightly
The price is $307
May 13 - May 14
Total with taxes and fees
Lovely Home Near the Art Museum

StayCozy at The Frankford

StayCozy at The Frankford
4.0 star property
North Philadelphia
8.8 out of 10, Excellent, (120 reviews)
"Clean, reasonable price. Good location."
United States
Jeffrey
$171 nightly
The price is $197
May 11 - May 12
Total with taxes and fees
StayCozy at The Frankford

Chic & Cozy Philly Stay in City Center

Chic & Cozy Philly Stay in City Center
3.0 star property
South Philadelphia
8.0 out of 10, Very Good, (5 reviews)
"Very warm and comfy spot! Definitely going to save this stay when coming back. There was extra pillow and blankets. Great place to stay!!"
United States
Genessis
$269 nightly
The price is $310
May 10 - May 11
Total with taxes and fees
Chic & Cozy Philly Stay in City Center

Quaint 3rd Floor Loft

Quaint 3rd Floor Loft
Upper Darby
9.4 out of 10, Exceptional, (20 reviews)
"Welcoming host, quiet property, toiletries & water were a nice touch"
United States
Courtney K M.
$138 nightly
The price is $152
May 10 - May 11
Total with taxes and fees
Quaint 3rd Floor Loft

Retreat to this harmonious and tranquil apartment in the quiet neighborhood.

Retreat to this harmonious and tranquil apartment in the quiet neighborhood.
West Philadelphia
8.2 out of 10, Very Good, (26 reviews)
"It was pretty good for the price we paid, cleaning could’ve been better. All around it was pretty good."
United States
Your
$150 nightly
The price is $172
May 9 - May 10
Total with taxes and fees
Retreat to this harmonious and tranquil apartment in the quiet neighborhood.

2 bedroom with work space and high speed internet.

2 bedroom with work space and high speed internet.
North Philadelphia
9.6 out of 10, Exceptional, (42 reviews)
"Beautiful place nice and cozy for a quiet getaway in the city. "
United States
Agwah
$143 nightly
The price is $163
May 11 - May 12
Total with taxes and fees
2 bedroom with work space and high speed internet.

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Wilmington
8.8 out of 10, Excellent, (21 reviews)
"Great stay place was very clean very welcoming "
United States
Destiny J.
$169 nightly
The price is $173
May 10 - May 11
Total with taxes and fees
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Stylish Private Suite in the heart of Brandywine Valley

Stylish Private Suite in the heart of Brandywine Valley
Wilmington
10.0 out of 10, Exceptional, (200 reviews)
"Great time and friendly people "
United States
Karl
$211 nightly
The price is $218
May 11 - May 12
Total with taxes and fees
Stylish Private Suite in the heart of Brandywine Valley

Bryn Mawr Has It All

Bryn Mawr Has It All
Bryn Mawr
8.6 out of 10, Excellent, (7 reviews)
"Great location to walk around Bryn Mawr and enjoy everything the area has to offer. Our host couldn’t have been more accommodating."
United States
Nathaniel W.
$285 nightly
The price is $316
May 10 - May 11
Total with taxes and fees
Bryn Mawr Has It All

Riverside Retreat

Riverside Retreat
Camden
9.8 out of 10, Exceptional, (6 reviews)
"Darrian was amazing!! He was very nice and his communication was great! The place is nice, provided towels and washcloths! "
United States
Saniya R.
$251 nightly
The price is $276
May 9 - May 10
Total with taxes and fees
Riverside Retreat

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

Hidden Gem Townhome with 2 BRs -University City -near UPenn&Drexel
University City
10.0 out of 10, Exceptional, (28 reviews)
"Everything was great would definitely come here agian"
United States
keith l.
$285 nightly
The price is $326
May 11 - May 12
Total with taxes and fees
Hidden Gem Townhome with 2 BRs -University City -near UPenn&Drexel

Big 3BR Near *Art Museum*- Family Game Room+ Patio

Big 3BR Near *Art Museum*- Family Game Room+ Patio
North Philadelphia
10.0 out of 10, Exceptional, (33 reviews)
"The house is clean, comfortable and conveniently located."
United States
Martha M.
$346 nightly
The price is $396
May 11 - May 12
Total with taxes and fees
Big 3BR Near *Art Museum*- Family Game Room+ Patio

Brand New Modern Home /w Rooftop Downtown Skyview

Brand New Modern Home /w Rooftop Downtown Skyview
South Philadelphia
10.0 out of 10, Exceptional, (6 reviews)
"Cute, cozy little apartment. Super walkable area. Phil was very communicative. We’d definitely stay again. "
United States
Mandy M.
$138 nightly
The price is $157
Jun 8 - Jun 9
Total with taxes and fees
Brand New Modern Home /w Rooftop Downtown Skyview

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 $275
May 11 - May 12
Total with taxes and fees
Walkable Neighborhood: Updated Morton Home!

Modern 1BR Retreat in Fishtown

Modern 1BR Retreat in Fishtown
North Philadelphia
9.4 out of 10, Exceptional, (6 reviews)
"The apartment was well maintained , top floor great lighting with the skylight s and windows.. Great location easy to walk to great restaurants, coffee shops, easy access to Septa and into Center City."
United States
Ann
$190 nightly
The price is $192
May 10 - May 11
Total with taxes and fees
Modern 1BR Retreat in Fishtown

Easy Walk 2 Stadiums- Kid Friendly | Game Room

Easy Walk 2 Stadiums- Kid Friendly | Game Room
South Philadelphia
10.0 out of 10, Exceptional, (46 reviews)
"Clean and easy check in process ! "
United States
Jordan
$320 nightly
The price is $367
May 11 - May 12
Total with taxes and fees
Easy Walk 2 Stadiums- Kid Friendly | Game Room

Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (35 reviews)
"Loved the location and place was comfortable. Our dogs loved the fenced back yard."
United States
James C.
$313 nightly
The price is $355
May 11 - May 12
Total with taxes and fees
Underground Railroad Barn
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

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 $136 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.

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?

Charming 3-bedroom house with WiFi and AC in wonderful Philadelphia: This vacation home rental near Chester has air-conditioning and WiFi 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?

Ridley Creek and Ethel Waters 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.