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.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was $621, price is now $527 per person
$527
per person
Oct 2 - Oct 5
found 21 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
Free WiFi in public areas is available at this hotel. Business travelers can take advantage of the business center. Take advantage of the free self parking.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,227, price is now $967 per person
$967
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Sarasota (SRQ) 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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $717, price is now $580 per person
$580
per person
Oct 2 - Oct 5
found 21 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $748, price is now $607 per person
$607
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Sarasota (SRQ) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.
Landing Furnished Apartments near YSM

Landing Furnished Apartments near YSM

3 out of 5
Downtown New Haven
Price was $683, price is now $571 per person
$571
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Sarasota (SRQ) to New Haven (HVN)
A gym is featured at this apartment, along with free WiFi in public areas and a virtual front desk.

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
$98 nightly
The price is $113 total per night
$113 total
Jul 19 - Jul 20
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.
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $111 total per night
$111 total
Jul 8 - Jul 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. There's a gym and multilingual staff can provide around-the-clock assistance.
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
Reserve now, pay when you stay
$96 nightly
The price is $111 total per night
$111 total
Jul 8 - Jul 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.
Pet friendly
Parking included
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
$80 nightly
The price is $92 total per night
$92 total
Jul 21 - Jul 22
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
$72 nightly
The price is $83 total per night
$83 total
Jul 12 - Jul 13
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.
Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

3 out of 5
10 Laura Blvd Norwich CT
Free Cancellation
$105 nightly
The price is $121 total per night
$121 total
Jul 19 - Jul 20
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Unwind with a drink at the bar/lounge and enjoy perks like free self parking and a free casino shuttle.
Pool
Parking included
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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 $527, 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.