Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

Stylish Private Suite  in the heart of Brandywine Valley

Stylish Private Suite in the heart of Brandywine Valley

Wilmington
The price is AU$304 per night from 20 Nov to 21 Nov
AU$304
includes taxes & fees
20 Nov - 21 Nov
Located in Wilmington, this vacation home is a 1-minute drive from Brandywine Valley and 5 minutes from Brandywine Creek State Park.
Stylish Private Suite in the heart of Brandywine Valley
Homey Retreat in Historic Kennett Square!!

Homey Retreat in Historic Kennett Square!!

Kennett Square
With a stay at this vacation home in Kennett Square, you'll be within a 10-minute drive of Longwood Gardens and Anson B. Nixon Park.
Homey Retreat in Historic Kennett Square!!
Beautiful Philadelphia Home

Beautiful Philadelphia Home

Philadelphia
With a stay at this vacation home in Philadelphia (North Philadelphia), you'll be a 4-minute drive from Temple University and 7 minutes from Pennsylvania Convention ...
Beautiful Philadelphia Home
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Beautiful Rittenhouse Square House 4 bedroom and 2 baths

Beautiful Rittenhouse Square House 4 bedroom and 2 baths

Philadelphia
The price is AU$252 per night from 2 Dec to 3 Dec
AU$252
includes taxes & fees
2 Dec - 3 Dec
Located in Philadelphia (Center City), this vacation home is within a 10-minute walk of Rittenhouse Square and University of Pennsylvania.
Beautiful Rittenhouse Square House 4 bedroom and 2 baths
Heart Of South Philly

Heart Of South Philly

Philadelphia
The price is AU$573 per night from 18 Nov to 19 Nov
AU$573
includes taxes & fees
18 Nov - 19 Nov
With a stay at this vacation home, you'll be centrally located in Philadelphia, within a 5-minute drive of Lincoln Financial Field and Citizens Bank Park.
Heart Of South Philly
Modern, Chef's Kitchen, Rooftop Deck, 6 Beds, 3 Spa-Like Bathrooms

Modern, Chef's Kitchen, Rooftop Deck, 6 Beds, 3 Spa-Like Bathrooms

Philadelphia
With a stay at this vacation home in Philadelphia (South Philadelphia), you'll be within a 5-minute drive of Rittenhouse Square and Pennsylvania Convention ...
Modern, Chef's Kitchen, Rooftop Deck, 6 Beds, 3 Spa-Like Bathrooms
A Glamorous Gem just 13mins from downtown/9mins from Zoo!

A Glamorous Gem just 13mins from downtown/9mins from Zoo!

Philadelphia
With a stay at this vacation home in Philadelphia (North Philadelphia), you'll be a 4-minute drive from Temple University and 8 minutes from Pennsylvania Convention ...
A Glamorous Gem just 13mins from downtown/9mins from Zoo!
NO CLEANING FEE  Newly renovated Home near Philly Sports Complex & Airport

NO CLEANING FEE Newly renovated Home near Philly Sports Complex & Airport

2 out of 5
Philadelphia
With a stay at this vacation home in Philadelphia (South Philadelphia), you'll be within a 5-minute drive of University of Pennsylvania and Lincoln Financial ...
NO CLEANING FEE Newly renovated Home near Philly Sports Complex & Airport
Luxurious 3-bedroom house in pleasant Point Breeze Philadelphia with WiFi & AC

Luxurious 3-bedroom house in pleasant Point Breeze Philadelphia with WiFi & AC

2 out of 5
Philadelphia
The price is AU$782 per night from 18 Nov to 19 Nov
AU$782
includes taxes & fees
18 Nov - 19 Nov
With a stay at this vacation home in Philadelphia (South Philadelphia), you'll be within a 5-minute drive of University of Pennsylvania and Rittenhouse ...
Luxurious 3-bedroom house in pleasant Point Breeze Philadelphia with WiFi & AC
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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.

Chester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester vacation homes are the perfect way for you to wing it.

Holiday houses in Chester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chester Holiday Homes essential information

Accommodation
449 Holiday Homes
Lowest Price
AU$196
Highest Price
AU$782
Popular accommodation
Stylish Private Suite in the heart of Brandywine Valley, Homey Retreat in Historic Kennett Square!!, Beautiful Philadelphia Home, Beautiful Rittenhouse Square House 4 bedroom and 2 baths, Heart Of South Philly, Modern, Chef's Kitchen, Rooftop Deck, 6 Beds, 3 Spa-Like Bathrooms , A Glamorous Gem just 13mins from downtown/9mins from Zoo!, NO CLEANING FEE Newly renovated Home near Philly Sports Complex & Airport, Luxurious 3-bedroom house in pleasant Point Breeze Philadelphia with WiFi & AC

Top trending hotels in Chester

Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

4 out of 5
1628 Chestnut St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is AU$245 per night from 17 Dec to 18 Dec
AU$245
includes taxes & fees
17 Dec - 18 Dec
With a stay at Club Quarters Hotel Rittenhouse Square, Philadelphia, you'll be centrally located in Philadelphia, just a 5-minute walk from Rittenhouse Square ...
Club Quarters Hotel Rittenhouse Square, Philadelphia
Sonesta Philadelphia Rittenhouse Square

Sonesta Philadelphia Rittenhouse Square

4 out of 5
1800 Market St, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is AU$248 per night from 28 Nov to 29 Nov
AU$248
includes taxes & fees
28 Nov - 29 Nov
With a stay at Sonesta Philadelphia Rittenhouse Square, you'll be centrally located in Philadelphia, within a 10-minute walk of City Hall and The Franklin ...
Sonesta Philadelphia Rittenhouse Square
Wyndham Philadelphia Historic District

Wyndham Philadelphia Historic District

3.5 out of 5
400 Arch Street, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is AU$228 per night from 25 Nov to 26 Nov
AU$228
includes taxes & fees
25 Nov - 26 Nov
Located in Philadelphia (Center City), Wyndham Philadelphia Historic District is within a 10-minute walk of Liberty Bell Center and Independence Hall.
Wyndham Philadelphia Historic District
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Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4 out of 5
4509 Island Ave, Philadelphia, PA
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 24 Nov to 25 Nov
AU$196
includes taxes & fees
24 Nov - 25 Nov
Located in Philadelphia (Southwest Philadelphia), Doubletree by Hilton Philadelphia Airport is within a 10-minute drive of Citizens Bank Park and Wells Fargo ...
Doubletree by Hilton Philadelphia Airport
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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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^Subject to availability and chosen travel dates.