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 Pathmaker Hotel
CA $1,029
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Bangor (BGR)
9.8/10 Exceptional! (693 reviews)
We really enjoyed staying here and just happened to get lucky with a last minute someone else checking out early. Staff was great. Rooms were nice and clean and comfortable. Thank you!
Reviewed on Oct 14, 2026
Hotel Ursa
CA $1,031
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Bangor (BGR)
9.6/10 Exceptional! (900 reviews)
The hotel itself was beautiful! It’s located on a college campus, which I had no idea about being from out of town. The property was clean, charming, and had a unique atmosphere that really set it apart from a typical hotel.
Unfortunately, the sleeping accommodations left a lot to be desired. The beds were extremely uncomfortable, and there was a very bright light on the AC unit near the ceiling that made it difficult to sleep. Between the two, I got little to no rest during my stay.
I truly hate to leave a less-than-positive review because the hotel has so much charm and potential. However, a good night’s sleep is one of the most important parts of a hotel stay, and unfortunately, that was the one thing this experience was missing. I hope these are things that can be improved because otherwise, it really is a lovely place!
Reviewed on Oct 14, 2026
The Lucerne Inn
Lucerne-in-Maine
CA $1,092
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Bangor (BGR)
8.8/10 Excellent! (1,007 reviews)
The hotel was very busy due to the fall peeper season. Our room overlooked a dance floor and was under the pub. We booked last minute so we were happy to at least get a room but the noise kept us up many hours. The breakfast consisted of frozen Jimmy Dean biscuits in an ice chest, yogurt, slices of cake wrapped to go and fruit. Couldn’t get anyone to provide water. There was coffee and one container of orange juice. We ate a light dinner at the restaurant and the food was okay. Eggplant sticks and crab cake. Our waitress was nice and fun to talk with. The view was amazing.
Reviewed on Oct 14, 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! (3 reviews)
"The cabin was great for my me and my son while we visited Maine to climb Mt. Katahdin! Clean and perfectly located for activities around northern Maine. The host was excellent and very accommodating to all our asks! Thanks for helping make our trip a memorable experience!"
Reviewed on Oct 4, 2026
Gateway Inn
1963 Medway Road Medway ME
Fully refundableReserve now, pay when you stay
CA $142
CA $155 total
Oct 15 - Oct 16
includes taxes & fees
8.6/10 Excellent! (504 reviews)
"Clean room"
Reviewed on Oct 12, 2026
Baxter Park Inn
935 Central St Millinocket ME
Fully refundableReserve now, pay when you stay
CA $189
CA $206 total
Nov 1 - Nov 2
includes taxes & fees
8.6/10 Excellent! (630 reviews)
"Well worth the stay, very friendly staff!"
Reviewed on Oct 11, 2026
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 $1,026 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.
