Chester Vacation Packages
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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.
The Woods of Eden Glampground
CA $1,828
per person
Oct 16 - Oct 19
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
10/10 Exceptional! (2 reviews)
We absolutely LOVED our experience at the glampground! It exceeded our expectations. The owner thought of every detail, and even reached out with Acadia tips and things to know ahead of time. If we come back to Acadia again, we will definitely have this place at the top of our list!
Reviewed on Aug 10, 2026
Eden Village Motel & Cottages
CA $1,934
per person
Oct 16 - Oct 19
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
8.8/10 Excellent! (288 reviews)
Camp Deforest is delightful. I wish we would have booked a longer stay. It’s clean, extremely charming, great family activities, and it’s close to locations for day trips.
Reviewed on Aug 28, 2026
Heathwood Inn
CA $1,884
per person
Oct 16 - Oct 19
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
8.2/10 Very good! (204 reviews)
This was a great place to stay. Was very comfortable and the inn was a beautiful place. I was surprised, I thought that breakfast was on site. Breakfast is offsite and I never wound up eating it so that is something to remember if you’re expecting to be able to walk downstairs to eat breakfast. But overall very comfortable and a great place to stay. It was extremely relaxing to be there and quiet.
Reviewed on Aug 27, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Quaint 1 Bedroom + Loft/1 Bath streamside Timber Frame cabin near Lincoln, ME.
Chester ME
10/10 Exceptional! (2 reviews)
"Jim was a great host. Very attentive and friendly. We will definitely stay again."
Reviewed on Aug 26, 2026
Baxter Park Inn
935 Central St Millinocket ME
Fully refundableReserve now, pay when you stay
CA $212
CA $232 total
Sep 29 - Sep 30
includes taxes & fees
Gateway Inn
1963 Medway Road Medway ME
Fully refundableReserve now, pay when you stay
CA $138
CA $151 total
Sep 2 - Sep 3
includes taxes & fees
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.
Frequently asked questions
How much does a Chester vacation package cost?
Offering excellent value package deals from CA $1,273 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?
- 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.
- 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.
- 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.
- 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.
