Deals on vacations and trips to Chester

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Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Milford - New Haven

Red Roof Inn Milford - New Haven

2 out of 5
Price was $407, price is now $369 per person
$369
per person
Mar 19 - Mar 22
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A safe deposit box and laundry facilities are also provided.
Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was $482, price is now $419 per person
$419
per person
Mar 19 - Mar 22
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
A golf course and a gym are featured at this smoke-free hotel. 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.
Springhill Suites Milford

Springhill Suites Milford

3 out of 5
Price was $468, price is now $440 per person
$440
per person
Mar 19 - Mar 22
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
Price was $471, price is now $453 per person
$453
per person
Mar 19 - Mar 22
found 17 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Enjoy the seasonal outdoor pool and perks like free WiFi. You'll appreciate the hot tub, bar/lounge, and laundry facilities.

Top Chester hotels deals

Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
$211 nightly
The price is $239 total per night
$239 total
Feb 1 - Feb 2
Total with taxes and fees
This luxury resort features a golf course, a casino, and a full-service spa. Families will appreciate the arcade/game room, onsite laundry facilities, and babysitting. Enjoy a meal in one of the 19 restaurants and free perks like valet parking and a casino shuttle.
Pool
Hot Tub
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
$93 nightly
The price is $107 total per night
$107 total
Jan 21 - Jan 22
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.
Pool
Breakfast included
Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

3 out of 5
10 Laura Blvd Norwich CT
Free Cancellation
$85 nightly
The price is $98 total per night
$98 total
Feb 10 - Feb 11
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
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Free Cancellation
$67 nightly
The price is $77 total per night
$77 total
Jan 19 - Jan 20
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.
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
$67 nightly
The price is $77 total per night
$77 total
Feb 1 - Feb 2
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.
Breakfast included
Parking included
Hampton Inn Norwich

Hampton Inn Norwich

2.5 out of 5
154 Salem Turnpike Norwich CT
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $117 total per night
$117 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features an indoor pool and a gym. 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 self-serve breakfast and free self parking.
Pool
Breakfast 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.

Popular places to visit

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.

Chester Creek Marina

Norma Terris Theater

You can enjoy a show at Norma Terris Theater on your trip to Chester. While you're in the area, stroll along the beautiful beaches.

Norma Terris Theater

Frequently asked questions

How much are vacation packages to Chester?
Starting at just $369, 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

Enjoying a #weekend out in #Connecticut #Marina #River #Autumn
Enjoying a #weekend out in #Connecticut #Marina #River #Autumn
Hands down the place to be in Chester!!!!
Where it all started! Lovely place for a cocktail!!