Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Price was $668, price is now $544 per person
$544
per person
Oct 9 - Oct 12
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $2,169, price is now $928 per person
$928
per person
Oct 9 - Oct 12
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,851, price is now $1,375 per person
$1,375
per person
Oct 9 - Oct 12
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This aparthotel features a gym and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, express check-out, and dry cleaning are also on offer.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,485, price is now $1,122 per person
$1,122
per person
Oct 9 - Oct 12
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $678, price is now $551 per person
$551
per person
Oct 9 - Oct 12
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Chester hotels deals

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $117 total per night
$117 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
1954 Norwich New London Tpke Montville CT
Free Cancellation
Reserve now, pay when you stay
$78 nightly
The price is $90 total per night
$90 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. The front desk is staffed around-the-clock and laundry facilities are on offer.
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Free Cancellation
$71 nightly
The price is $82 total per night
$82 total
Sep 10 - Sep 11
Total with taxes and fees
A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
$89 nightly
The price is $102 total per night
$102 total
Sep 8 - Sep 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
201 Washington Avenue North Haven CT
Free Cancellation
$112 nightly
The price is $129 total per night
$129 total
Sep 27 - Sep 28
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.
The Spa at Norwich Inn

The Spa at Norwich Inn

3.5 out of 5
607 W Thames St Norwich CT
Free Cancellation
Reserve now, pay when you stay
$213 nightly
The price is $245 total per night
$245 total
Sep 7 - Sep 8
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this historic hotel. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, bar/lounge, and laundry facilities.
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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.

Stay near popular Chester attractions

Chester Creek Marina

Explore the waterfront in Chester with a trip to Chester Creek Marina. While you're in the area, stroll along the beautiful beaches.
See properties

Frequently asked questions

How much are vacation packages to Chester?
Starting at just $544, hotel and flight packages are a great way to make your vacation budget stretch further. Chester, here you come!
Where can I get the best vacation package deals for Chester?
No matter what you enjoy doing, Travelocity can help you find the perfect Chester package deal. All you need to do is select a combination from our 400 airlines and 1,000,000 properties across the globe.
Why should I purchase my Chester vacation bundle with Travelocity?
From our 24/7 customer support to our range of exhilarating destinations, we are committed to fulfilling your travel dreams. All you have to do is to click and book — our Price Match Guarantee will ensure you lock in the lowest price.
Will I save money on my Chester car rental if I bundle it with hotels and flights?
With a Chester vacation package, you can bundle your hotel, flight and car bookings and save a ton. If you want to explore the best of this fabulous city, why not start with Times Square? This renowned attraction is 90 mi from Chester. With a rental car, you'll be there belong long.
Which airport is best for Chester?
Many travelers fly into Bradley Intl. Airport (BDL), 40 mi north of downtown Chester. Others prefer T.F. Green Airport (PVD) (60 mi away from central Chester) or MacArthur Airport (ISP) (55 mi away from central Chester).
What is there to do in Chester?
Chester Creek Marina deserves to be on your travel schedule. After you've crossed off this popular attraction, simply roam through the streets of Chester and experience what makes this cool place tick.
Where should I stay when visiting Chester?
If you're searching for somewhere to base yourself, have a look at the Updated cottage "Beriozka" on Cedar Lake. It's the top choice for many visitors.

Photos of local treasures

Browse Chester vacation photos for more inspiration

A calm river with boats, wooden docks, and buildings along the shore.
A historic waterfront estate with a large white building featuring a balcony and a flagpole.
A marina with boats docked, surrounded by autumn foliage and a cloudy sky.