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.
Sea Meadow Inn

Sea Meadow Inn

4 out of 5
Save 100% on your flight
Price was $1,165, price is now $798 per person
$798
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
This bed & breakfast features free WiFi in public areas, wedding services, and free self parking. Enjoy the free full breakfast each morning. A terrace, a garden, and luggage storage are also on offer.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $6,388, price is now $4,043 per person
$4,043
per person
Aug 26 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
A private beach and a hot tub are featured at this guesthouse. Enjoy a day at the beach kayaking, or relax with sun loungers. WiFi in public areas is free.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $1,834, price is now $1,240 per person
$1,240
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,367, price is now $927 per person
$927
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,966, price is now $1,345 per person
$1,345
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

Top Chester hotels deals

La Quinta Inn & Suites by Wyndham Salem NH

La Quinta Inn & Suites by Wyndham Salem NH

3 out of 5
8 Keewaydin Dr Salem NH
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $103 total per night
$103 total
Jul 6 - Jul 7
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd Andover MA
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $130 total per night
$130 total
Jul 5 - Jul 6
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. Guests will appreciate freebies like continental breakfast and free self parking.
Comfort Inn Manchester Airport

Comfort Inn Manchester Airport

2.5 out of 5
298 Queen City Ave Manchester NH
Free Cancellation
$103 nightly
The price is $112 total per night
$112 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.
Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

3 out of 5
13500 S Willow St Manchester NH
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $108 total per night
$108 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.
DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St. Manchester NH
Free Cancellation
Reserve now, pay when you stay
$123 nightly
The price is $134 total per night
$134 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Self parking, a business center, and a coffee shop are also offered.
Park View Inn - Salem

Park View Inn - Salem

2 out of 5
109 S Broadway Salem NH
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $99 total per night
$99 total
Jul 14 - Jul 15
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
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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 Town Hall

After visiting Chester Town Hall, make a plan to see the other sights and activities in Chester.
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Frequently asked questions

How much are vacation packages to Chester?
Enjoy a memorable travel experience in Chester with a vacation package starting from as low as $798. Locking in hotels, flights and tours with Travelocity is a breeze. What's more, our great deals will leave you with more money in your pocket for loads of fun times.
Where can I get the best vacation package deals for Chester?
For the perfect Chester package deal, turn to Travelocity. Choose from 400 partner airlines and 1,000,000 worldwide properties to create the ideal trip — it's really that easy.
Why should I book my Chester vacation bundle via Travelocity?
Incredible savings, loads of enticing destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.
Can I save on my Chester car rental if I book it with my hotel or flight?
With a Chester vacation package, you can bundle your car, flight and hotel bookings and save some serious money. If you'd love to uncover the best of this fantastic city, why not check out Fenway Park? This popular attraction is 45 mi from Chester. With your own set of wheels, you'll be there soon enough.
Which airport is best for Chester?
Logan Intl. Airport (BOS), 45 mi south of the city center, is where many visitors begin their Chester adventures. That said, Manchester-Boston Regional Airport (MHT) (9 mi away from central Chester) could be the more convenient option for you.
Where should I stay when visiting Chester?
The Beautiful country Cottage located on Apple farm. Beautiful fall foliage! is popular with many travelers. Book now before it's too late.

Photos of local treasures

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