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.
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $648, price is now $473 per person
$473
per person
Mar 19 - Mar 23
found 10 hours ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a business center, and a coffee shop are also offered.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,196, price is now $517 per person
$517
per person
Feb 8 - Feb 12
found 7 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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 Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $773, price is now $554 per person
$554
per person
Mar 19 - Mar 23
found 10 hours ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A coffee shop, a library, and a computer station are also on offer.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,084, price is now $778 per person
$778
per person
Feb 13 - Feb 17
found 15 hours ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $808, price is now $582 per person
$582
per person
Mar 19 - Mar 23
found 10 hours ago
Roundtrip flight included
Tampa (TPA) 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
$137 nightly
The price is $149 total per night
$149 total
Jan 11 - Jan 12
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.
Pool
Free WiFi
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
$99 nightly
The price is $111 total per night
$111 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.
Pool
Breakfast included
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
$77 nightly
The price is $84 total per night
$84 total
Jan 6 - Jan 7
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.
Hampton Inn & Suites Exeter

Hampton Inn & Suites Exeter

2.5 out of 5
59 Portsmouth Ave Exeter NH
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $102 total per night
$102 total
Jan 11 - Jan 12
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.
Pool
Breakfast included
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
$119 nightly
The price is $133 total per night
$133 total
Jan 11 - Jan 12
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.
Pool
Breakfast included
EVEN Hotel Manchester Airport by IHG

EVEN Hotel Manchester Airport by IHG

3.5 out of 5
55 John E. Devine Drive Manchester NH
Get rates
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. Free self parking, a snack bar/deli, and a lobby fireplace are also offered.
Pool
Pet friendly
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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 $473. 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