Cheap Vacations in Chester County

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Chester County vacations

Price found within the past 48 hours. Click for updated prices.
Valley Forge Casino Resort

Valley Forge Casino Resort

4 out of 5
Price was $527, price is now $377 per person
$377
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Casa De Miliki

Casa De Miliki

3 out of 5
South Philadelphia
Price was $4,838, price is now $2,553 per person
$2,553
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
Tudor Lux

Tudor Lux

4 out of 5
Price was $6,713, price is now $4,521 per person
$4,521
per person
Oct 13 - Oct 17
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
YOWIE (Hotel & Shop)

YOWIE (Hotel & Shop)

2 out of 5
South Philadelphia
Price was $851, price is now $624 per person
$624
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Hyatt Centric Rittenhouse Square Philadelphia

Hyatt Centric Rittenhouse Square Philadelphia

4 out of 5
Center City
Price was $815, price is now $613 per person
$613
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
The Lily Inn

The Lily Inn

3 out of 5
Save 100% on your flight
Price was $590, price is now $444 per person
$444
per person
Oct 21 - Oct 25
found 19 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

3 out of 5
Center City
Price was $713, price is now $552 per person
$552
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Kimpton Hotel Palomar Philadelphia by IHG

Kimpton Hotel Palomar Philadelphia by IHG

4.5 out of 5
Center City
Price was $998, price is now $775 per person
$775
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Hotel Anna & Bel

Hotel Anna & Bel

4 out of 5
North Philadelphia
Save 100% on your flight
Price was $1,538, price is now $1,199 per person
$1,199
per person
Oct 21 - Oct 25
found 19 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Guild House Hotel

Guild House Hotel

3 out of 5
Center City
Save 100% on your flight
Price was $1,248, price is now $974 per person
$974
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)

3-night Chester County vacations

Price found within the past 48 hours. Click for updated prices.
La Reserve on Pine

La Reserve on Pine

3.5 out of 5
Price was $620, price is now $520 per person
$520
per person
Oct 20 - Oct 23
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Casa De Miliki

Casa De Miliki

3 out of 5
Price was $4,838, price is now $2,553 per person
$2,553
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
YOWIE (Hotel & Shop)

YOWIE (Hotel & Shop)

2 out of 5
Price was $851, price is now $624 per person
$624
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Guild House Hotel

Guild House Hotel

3 out of 5
Save 100% on your flight
Price was $1,248, price is now $974 per person
$974
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Kimpton Hotel Palomar Philadelphia by IHG

Kimpton Hotel Palomar Philadelphia by IHG

4.5 out of 5
Price was $1,060, price is now $829 per person
$829
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Philadelphia (PHL)
Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

3 out of 5
Price was $867, price is now $684 per person
$684
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
The Bellevue Hotel - The Unbound Collection by Hyatt

The Bellevue Hotel - The Unbound Collection by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,836, price is now $1,463 per person
$1,463
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
The Windsor Suites

The Windsor Suites

4 out of 5
Price was $900, price is now $717 per person
$717
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Hyatt Centric Rittenhouse Square Philadelphia

Hyatt Centric Rittenhouse Square Philadelphia

4 out of 5
Price was $1,139, price is now $910 per person
$910
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Society Hill Hotel

Society Hill Hotel

2 out of 5
Price was $684, price is now $557 per person
$557
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
The Westin Philadelphia

The Westin Philadelphia

4 out of 5
Price was $1,224, price is now $1,004 per person
$1,004
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)
Philadelphia Marriott Old City

Philadelphia Marriott Old City

4 out of 5
Price was $899, price is now $745 per person
$745
per person
Oct 24 - Oct 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Philadelphia (PHL)

4-night Chester County vacations

Price found within the past 48 hours. Click for updated prices.
Trolley Stop Motel

Trolley Stop Motel

2 out of 5
Price was $496, price is now $357 per person
$357
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Casa De Miliki

Casa De Miliki

3 out of 5
Price was $7,062, price is now $3,780 per person
$3,780
per person
Oct 13 - Oct 17
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Tudor Lux

Tudor Lux

4 out of 5
Price was $6,713, price is now $4,521 per person
$4,521
per person
Oct 13 - Oct 17
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
YOWIE (Hotel & Shop)

YOWIE (Hotel & Shop)

2 out of 5
Save 100% on your flight
Price was $1,509, price is now $1,022 per person
$1,022
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Philadelphia (PHL)
The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Save 100% on your flight
Price was $2,826, price is now $1,985 per person
$1,985
per person
Oct 21 - Oct 25
found 19 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
The Conwell Inn

The Conwell Inn

2.5 out of 5
Price was $555, price is now $405 per person
$405
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
The Windsor Suites

The Windsor Suites

4 out of 5
Price was $978, price is now $727 per person
$727
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Philadelphia (PHL)
The Lily Inn

The Lily Inn

3 out of 5
Save 100% on your flight
Price was $590, price is now $444 per person
$444
per person
Oct 21 - Oct 25
found 19 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Sofitel Philadelphia at Rittenhouse Square

Sofitel Philadelphia at Rittenhouse Square

4.5 out of 5
Price was $1,145, price is now $878 per person
$878
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Philadelphia (PHL)
New Season Royals

New Season Royals

2 out of 5
Save 100% on your flight
Price was $699, price is now $540 per person
$540
per person
Oct 21 - Oct 25
found 19 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Hampton Inn Philadelphia Center City-Convention Center

Hampton Inn Philadelphia Center City-Convention Center

3 out of 5
Price was $903, price is now $701 per person
$701
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Philadelphia (PHL)
Hotel Anna & Bel

Hotel Anna & Bel

4 out of 5
Save 100% on your flight
Price was $1,538, price is now $1,199 per person
$1,199
per person
Oct 21 - Oct 25
found 19 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)

5-night Chester County vacations

Price found within the past 48 hours. Click for updated prices.
Greystone Manor Bed & Breakfast

Greystone Manor Bed & Breakfast

3 out of 5
Price was $956, price is now $794 per person
$794
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Philadelphia (PHL)
Bird In Hand Village Inn & Suites

Bird In Hand Village Inn & Suites

3 out of 5
Price was $998, price is now $860 per person
$860
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Philadelphia (PHL)
The Cabins at Beaver Creek

The Cabins at Beaver Creek

3.5 out of 5
Price was $1,119, price is now $1,031 per person
$1,031
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Philadelphia (PHL)
Valley Forge Casino Resort

Valley Forge Casino Resort

4 out of 5
Price was $981, price is now $805 per person
$805
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

3 out of 5
Price was $1,129, price is now $935 per person
$935
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
One Sky Loft

One Sky Loft

2 out of 5
Price was $1,036, price is now $863 per person
$863
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
Sofitel Philadelphia at Rittenhouse Square

Sofitel Philadelphia at Rittenhouse Square

4.5 out of 5
Price was $1,305, price is now $1,098 per person
$1,098
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
Philadelphia Marriott Old City

Philadelphia Marriott Old City

4 out of 5
Price was $1,208, price is now $1,038 per person
$1,038
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
The Conwell Inn

The Conwell Inn

2.5 out of 5
Price was $964, price is now $828 per person
$828
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
The Windsor Suites

The Windsor Suites

4 out of 5
Price was $1,107, price is now $955 per person
$955
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
Riversuites at The Battery

Riversuites at The Battery

2.5 out of 5
Price was $1,174, price is now $1,022 per person
$1,022
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
Courtyard by Marriott Philadelphia Downtown

Courtyard by Marriott Philadelphia Downtown

4 out of 5
Price was $1,056, price is now $926 per person
$926
per person
Oct 16 - Oct 20
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)

6-7 night Chester County vacations

Price found within the past 48 hours. Click for updated prices.
Four Points By Sheraton Philadelphia Airport

Four Points By Sheraton Philadelphia Airport

3 out of 5
Price was $534, price is now $406 per person
$406
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Sofitel Philadelphia at Rittenhouse Square

Sofitel Philadelphia at Rittenhouse Square

4.5 out of 5
Save 100% on your flight
Price was $1,242, price is now $832 per person
$832
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Chic & Cozy Philly Stay in City Center

Chic & Cozy Philly Stay in City Center

3 out of 5
Save 100% on your flight
Price was $850, price is now $641 per person
$641
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Hyatt Centric Rittenhouse Square Philadelphia

Hyatt Centric Rittenhouse Square Philadelphia

4 out of 5
Price was $1,803, price is now $1,386 per person
$1,386
per person
Oct 19 - Oct 25
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
One Sky Loft

One Sky Loft

2 out of 5
Save 100% on your flight
Price was $826, price is now $656 per person
$656
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Stylish Minimalist Stay in City Center

Stylish Minimalist Stay in City Center

3 out of 5
Price was $673, price is now $542 per person
$542
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

Fairfield Inn & Suites by Marriott Philadelphia Downtown/Center City

3 out of 5
Price was $1,256, price is now $1,015 per person
$1,015
per person
Oct 19 - Oct 25
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
4211 Suites

4211 Suites

4.5 out of 5
Price was $727, price is now $591 per person
$591
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
Aloft by Marriott Philadelphia Airport

Aloft by Marriott Philadelphia Airport

3 out of 5
Price was $587, price is now $478 per person
$478
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
StayCozy at The Arco

StayCozy at The Arco

2 out of 5
Price was $730, price is now $595 per person
$595
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
The Windsor Suites

The Windsor Suites

4 out of 5
Price was $1,537, price is now $1,252 per person
$1,252
per person
Oct 19 - Oct 25
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to Philadelphia (PHL)
Apartmint at 1149 N 3rd St Philladelphia

Apartmint at 1149 N 3rd St Philladelphia

2 out of 5
Price was $596, price is now $489 per person
$489
per person
Oct 12 - Oct 18
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)

Top places to visit in Chester County

A street lined with historic buildings, a sign for Kildogge's Pub, and a banner for West Chester Restaurant Week.
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West Chester

West Chester

Flight deals to Chester County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Oct 10 - Tue, Nov 10
ATL
Atlanta
PHL
Philadelphia
$38 Roundtrip, found 20 hours ago
$38
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Atlanta to Philadelphia, returning Tue, Nov 10, priced at $38 found 20 hours ago
Thu, Nov 5 - Sun, Nov 8
FLL
Fort Lauderdale
TTN
Trenton
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Nov 5 from Fort Lauderdale to Trenton, returning Sun, Nov 8, priced at $78 found 1 day ago
Thu, Oct 1 - Sun, Oct 4
PIE
St. Petersburg
TTN
Trenton
$83 Roundtrip, found 4 days ago
$83
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Thu, Oct 1 from St. Petersburg to Trenton, returning Sun, Oct 4, priced at $83 found 4 days ago

Top rated hotels for your Chester County vacation

Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

4 out of 5
1628 Chestnut St Philadelphia PA
Free Cancellation
Reserve now, pay when you stay
33.95 mi from city center
$160 nightly
The price is $186 total per night
$186 total
Sep 7 - Sep 8
Total with taxes and fees
A stay at Club Quarters Hotel Rittenhouse Square, Philadelphia places you in the heart of Philadelphia, within a 15-minute walk of Rittenhouse Square and Pennsylvania Convention Center.
Loews Philadelphia Hotel

Loews Philadelphia Hotel

4 out of 5
1200 Market St Philadelphia PA
Free Cancellation
Reserve now, pay when you stay
34.38 mi from city center
$179 nightly
The price is $208 total per night
$208 total
Sep 7 - Sep 8
Total with taxes and fees
With a stay at Loews Philadelphia Hotel, you'll be centrally located in Philadelphia, steps from Reading Terminal Market and within a 5-minute walk of Thomas Jefferson University Hospital.
Pet friendly
Free WiFi
The Windsor Suites

The Windsor Suites

4 out of 5
1700 Ben Franklin Pkwy Philadelphia PA
33.94 mi from city center
$127 nightly
The price is $147 total per night
$147 total
Sep 7 - Sep 8
Total with taxes and fees
A stay at The Windsor Suites places you in the heart of Philadelphia, within a 10-minute walk of Pennsylvania Convention Center and Fairmount Park.
Pool
Pet friendly
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.