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.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
Price was $756, price is now $515 per person
$515
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Boston (BOS)
The hotel's 24-hour gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,748, price is now $823 per person
$823
per person
Mar 7 - Mar 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,640, price is now $1,038 per person
$1,038
per person
Mar 7 - Mar 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,832, price is now $1,201 per person
$1,201
per person
Mar 19 - Mar 23
found 15 hours ago
Roundtrip flight included
Raleigh (RDU) 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.
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $781, price is now $542 per person
$542
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Boston (BOS)
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Top Chester hotels deals

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
$130 nightly
The price is $141 total per night
$141 total
Jan 18 - Jan 19
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.
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
$100 nightly
The price is $112 total per night
$112 total
Feb 1 - Feb 2
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.
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
$79 nightly
The price is $86 total per night
$86 total
Jan 18 - Jan 19
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.
Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston

2.5 out of 5
4 Tech Drive Andover MA
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $105 total per night
$105 total
Feb 5 - Feb 6
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

2 out of 5
76 Mountain Rd Epsom NH
$133 nightly
The price is $144 total per night
$144 total
Jan 20 - Jan 21
Total with taxes and fees
This cabin includes express check-out and a virtual front desk. Take advantage of the free self parking.
Hampton Inn Haverhill

Hampton Inn Haverhill

2.5 out of 5
106 Bank Road Haverhill MA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $109 total per night
$109 total
Jan 22 - Jan 23
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 and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
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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 Town Hall

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

Chester Town Hall

Chester Public Library

Chester Public Library is just one of the places to see in Chester, so why not enjoy the other things to explore during your travels?

Chester Public Library

Chester Village Cemetery

Enjoy a stop at Chester Village Cemetery, a landmark worth seeing in Chester.

Chester Village Cemetery

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 $515. 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

Browse Chester vacation photos for more inspiration