Chester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Chester Vacation

Art, food, entertainment and more … There's so much to discover with a Chester vacation package. And with the ability to easily customize your city break, it's guaranteed to be one that's tough to forget. In the mood for a bit of sightseeing? A trip to Chester isn't complete without exploring Lincoln Memorial Library, Jato Highlands Golf Course and other popular attractions. Don't delay visiting this destination any longer. Your dream Chester vacation is a couple of clicks away with Expedia.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Bangor

Super 8 by Wyndham Bangor

2 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
8/10 Very Good! (1,159 reviews)
Clean. Polite staff. easy.

Reviewed on Jul. 2, 2025

Country Inn at The Mall

Country Inn at The Mall

2 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
9.4/10 Exceptional! (2,288 reviews)
Great place very centrally located and clean. Price was awesome. Will definitely stay there again.

Reviewed on Jul. 8, 2025

Sugarloaf Mountain Hotel

Sugarloaf Mountain Hotel

3.5 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
9.2/10 Wonderful! (508 reviews)
Our reason for staying here was not because we were interested in the Sugarloaf Mountain area, but because it was the only hotel we could find for that night of our trip. ~ So, I would recommend it to anyone interested in all that Sugarloaf Mtn. has to offer. It's a beautiful hotel. We at dinner at the "45 North" restaurant located in the hotel because we didn't want to drive around looking for somewhere else, BUT order was very tasty, especially for the prices. ~ We didn't use any other amenities, but I'm sure they're top-notched. ~ We would not stay there again, because it was located out of our way and way too above our budget. Again, though, if someone likes what Sugarloaf Mtn. has to offer, I would highly recommend.

Reviewed on May 29, 2025

Hampton Inn Bangor

Hampton Inn Bangor

2.5 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
9.2/10 Wonderful! (1,004 reviews)
They have a pool, a large breakfast buffet with real food (cereal, fruit, yogurt, eggs, pancakes, toast, coffe, etc.), a laundry room, and very helpful front desk folks. Super clean rooms, really nice housekeeping staff, too.

Reviewed on Jul. 8, 2025

Bangor Grande

Bangor Grande

2.5 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
8.4/10 Very Good! (1,727 reviews)
We were offered an upgrade which was unexpected but quite nice. Staff was very friendly. Enjoyed our stay.

Reviewed on Jul. 10, 2025

Ready to book your vacation to Chester?

 

Choose your dates

Chester Hotel Deals

Cabin on the water!
Cabin on the water!
Chester
9.4/10 Exceptional! (23 reviews)
Really great place to stay
"Really nice cabin very clean well appointed the owner owners are fantastic to deal with"

Reviewed on Jul. 6, 2025

Get rates
Cabin on the water!
Baxter Park Inn
Baxter Park Inn
2 out of 5
935 Central St, Millinocket, ME
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Jul 13 to Jul 14
CA $197
CA $215 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (476 reviews)
"The hotel was conveniently located. The building and grounds were a little tired but the staff was clearly making an effort."

Reviewed on Jun. 30, 2025

Baxter Park Inn
Katahdin Inn & Suites
Katahdin Inn & Suites
2 out of 5
740 Central St, Millinocket, ME
The price is CA $109 per night from Aug 6 to Aug 7
CA $109
CA $119 total
Aug 6 - Aug 7
includes taxes & fees
7.8/10 Good! (148 reviews)
"Our assigned room had an air conditioning issue. Austin immediately"

Reviewed on Jul. 5, 2025

Katahdin Inn & Suites
See all 111 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from CA $688 on Expedia, you'll be pleasantly surprised at how much a vacation to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
To score cheap Chester vacation packages, organize your trip outside of peak periods like public holidays and major festivals. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Chester?
Usually, a handful of days is enough to tick off the top sights during your Chester vacation. But if you prefer to have more time to rest or go on day tours, think about extending your itinerary.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Chester package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chester getaway off to a flying start.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customize your Chester escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
If you're planning an impromptu Chester vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Chester?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Chester.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to set aside for your trip to Chester. Then, pick a property that works with your budget, whether that's a wallet-friendly stay or a lavish retreat.
  3. Decide how long to go away for: Now that you're more familiar with Chester, you can work out the right length of your break. Pull together a rough plan and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Chester vacation package.

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