Chester Vacations from $576

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Your Chester Vacation

Say bye-bye to planning worries and hello to a Chester vacation package. With everything organized before you take off, you can focus on discovering every inch of this city, starting with Downtown Manchester, which is good for cafes, history and bars and pubs. Ready for some sightseeing? A trip to Chester isn't complete without exploring Zorvino Vineyards, Robert Frost Farm State Historic Site and other major attractions. Your perfect Chester vacation is a few clicks away. Search hotels, flights and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Jul 15 - Jul 19
found 16 hours ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
7.6/10 Good! (157 reviews)
The room and property were all fine, cookies and infused water in the lobby were nice. The only reason to not give it 5 stars is that i would not want people to think they were in a luxury location. It is an immaculate and quiet room in the city where there isn't a lot of space around it. Rooms open to the parking. Definitely at least 4.5 states

Reviewed on May 27, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
This is an upscale hotel with excellent amenities and wonderfully helpful and friendly people who kindly made our stay a joy.

Reviewed on May 27, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
9.2/10 Wonderful! (270 reviews)
Awesome, awesome, awesome. I could not find another word to describe my stay! Awesome.

Reviewed on May 22, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
9.6/10 Exceptional! (276 reviews)
This was one of the best hotel experiences I've had. The staff goes above and beyond to make you feel welcomed. From the Tates cookies and sparkling water available, to the water bottles at the end of the night, they really pay attention to small details, making it a great experience. The rooms were clean and roomy. We ended up walking the entire time in Boston since the hotel was at a great location, but if you plan on driving, keep in mind that you have to call ahead of time to access your car. Would definitely stay again!

Reviewed on May 28, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
9.4/10 Exceptional! (31 reviews)
Beautiful hotel, flowers in All areas. Staff was superb. Two very minor issue - no fan for toilet area, hot water in shower takes a bit. Doesn’t distract from my overall rating. Easily a come back recommendation

Reviewed on May 29, 2024

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
5,200
Top Sights
Canobie Lake Park, Bear Brook State Park and Zorvino Vineyards

Chester Hotel Deals

Country Inn & Suites by Radisson, Manchester Airport, NH
Country Inn & Suites by Radisson, Manchester Airport, NH
3 out of 5
250 S River Rd, Bedford, NH
Fully refundable
The price is $131 per night from Jun 5 to Jun 6
$131
$142 total
includes taxes & fees
Jun 5 - Jun 6
7.8/10 Good! (1,004 reviews)
"Our initial room was bad. They rented us a suite knowing the pull out couch was broken. They stated nothing else was available. They offered is a room with 1 bed or 2. My response was I rented a room with 3 beds. They offered 2 cots bit then we realized they wouldn’t fit in the room. They said they ..."

Reviewed on May 28, 2024

Country Inn & Suites by Radisson, Manchester Airport, NH
DoubleTree by Hilton Manchester Downtown
DoubleTree by Hilton Manchester Downtown
4 out of 5
700 Elm St., Manchester, NH
Fully refundableReserve now, pay when you stay
The price is $136 per night from Jun 30 to Jul 1
$136
$148 total
includes taxes & fees
Jun 30 - Jul 1
8.8/10 Excellent! (1,002 reviews)
"It was perfect for a quick overnight to the area"

Reviewed on May 28, 2024

DoubleTree by Hilton Manchester Downtown
Park View Inn - Salem
Park View Inn - Salem
2 out of 5
109 S Broadway, Salem, NH
Fully refundableReserve now, pay when you stay
The price is $109 per night from Jun 11 to Jun 12
$109
$119 total
includes taxes & fees
Jun 11 - Jun 12
8.6/10 Excellent! (1,003 reviews)
Stay here often
"This has been a go-to stay for years due to comfort, cleanliness and great value. But now prices are suddenly more in line with other area hotels so it looks like the great bargain days are over. Still a great location with access to Boston and the White Mountains of NH"

Reviewed on May 27, 2024

Park View Inn - Salem
See all 436 properties in Chester
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Starting from as low as $576, a vacation package is your portal to low-cost travel. Customize your Chester trip by selecting from our wide range of hotels, flights and rental cars.
How do I get a cheap travel package to Chester?
Book everything in one place with our Chester vacation packages. You’ll find bargains on hotels, flights, tours and more that’ll keep your wallet happy and your spirit of adventure alive. And, with more than 550 air carriers and 1,000,000 hotels throughout the world to pick from, you’ll have the flexibility to mix and match as you like.
What are the top hotels in Chester?
If it’s comfort and convenience you’re after, you can’t beat Private Cozy Country Cottage On A Beautiful Apple Orchard. Spend your evenings kicking back here and your days checking out Chester’s popular attractions.
How far in advance should I book my Chester vacation?
Savvy travelers often book as early as possible. You can usually look up international fares on Expedia up to 12 months before your intended flight. If you’ve left things to the last minute, don’t stress. Bargain prices sometimes become available in the last weeks prior to departure.
What does an Expedia Chester travel package include?
Travel packages include rental cars, flights and hotels, but you can mix and match them to create your ideal Chester trip. You can also add on tours and activities once you’ve made your booking. You’re the boss! When you bundle your bookings with Expedia, you’ll get access to discounts you won’t find anywhere else.
What should I know before booking a Chester travel package?
Booking all the parts of your trip together is a simple way to save. Bundle your car rentals, airfares and hotels into a convenient package. But you’re not limited to hotels. Expedia has all kinds of properties, including vacation rentals such as mountain cabins and city residences. The list goes on!
Can I choose my airline with a Chester Expedia vacation package?
Yes, and with over 550 airlines to select from globally, it’s all about choice. Search the available options and see which airline suits your budget and needs.
If I'm not able to travel, can I cancel my Chester vacation package?
Don’t worry if you’re rethinking your Chester vacation package — it’s possible to cancel or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally get that your circumstances can change suddenly, so make your way to our Customer Service Portal if that happens. When you’re ready to make changes, we’ll take care of it.

Discover the most popular places to visit in Chester

Image for Chester Village Cemetery

Chester Village Cemetery

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

Chester Village Cemetery

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.