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.
Country Inn at The Mall

Country Inn at The Mall

2 out of 5
Price was CA $1,294, price is now CA $1,145 per person
CA $1,145
per person
Sep 9 - Sep 13
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
9.4/10 Exceptional! (2,415 reviews)
Like the old country feel! Breakfast was great! Wish it would’ve had had an ice machine on the 2nd floor Was a good stay.

Reviewed on Jul 14, 2026

Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages

3 out of 5
Price was CA $3,194, price is now CA $2,712 per person
CA $2,712
per person
Aug 15 - Aug 22
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Bangor (BGR)
7.6/10 Good! (98 reviews)
Staff was wonderful plus some ! Cabin a bit musty but opened windows & everything was great. Cabin was very clean & bed was comfortable !!! Loved the girl that checked us in - Little confusion on my part & she couldn’t have been sweeter ❤️ AND… they just put in a pool !

Reviewed on Jul 14, 2026

Mount Battie Inn

Mount Battie Inn

2.5 out of 5
Price was CA $2,830, price is now CA $2,412 per person
CA $2,412
per person
Aug 15 - Aug 22
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Bangor (BGR)
8.8/10 Excellent! (325 reviews)
I don’t understand the praise - this is a motel-full stop.

Reviewed on Jul 7, 2026

3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Price was CA $6,896, price is now CA $5,972 per person
CA $5,972
per person
Aug 15 - Aug 22
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Bangor (BGR)
8/10 Very good! (4 reviews)
It was beautiful inside and out. Would recommend 10/10. Very quiet location beds slept great and close to Bar Harbor

Reviewed on Sep 30, 2025

Acadia Pines Motel

Acadia Pines Motel

2.5 out of 5
Price was CA $2,894, price is now CA $2,534 per person
CA $2,534
per person
Aug 15 - Aug 22
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Bangor (BGR)
7.4/10 Good! (308 reviews)
The location was alright. The room was outdated. The bathroom had rust on the heating unit. The cleaning lady did a nice job with what she had to work with. There seem to have a problem with the septic system for the flush didn’t always flush good.When the room was booked it said the pool would be open for the season 2026. When we arrived for a long weekend for July 4th the pool was closed and stayed closed until the last afternoon we were there. It was in the 90’s every day. The air conditioning unit did work.

Reviewed on Jul 10, 2026

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Chester Hotel Deals

Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.

Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.

Chester ME
10/10 Exceptional! (1 review)
"The lodge was exactly what we were looking for. It comfortably slept 4 and the HVAC kept it cool despite a hot week in Maine. Jim was a great host. He clearly communicated everything, met us at check in, and had the lodge stocked with toiletries, snacks, and some drinks. He’s thought of everything. ..."

Reviewed on Jul 9, 2026

Get rates
Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.
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 $181 per night from Jul 15 to Jul 16
CA $181
CA $197 total
Jul 15 - Jul 16
includes taxes & fees
8.6/10 Excellent! (569 reviews)
"I don't remember reading that there were cats in the Lobby. I am allergic so I try to keep away but needed to use the laundry. The room was fine and the bed was comfortable. The staff was great and friendly. The side parking lot needs to be levelled out. There were a few dips but manageable. Overall, ..."

Reviewed on Jul 10, 2026

Baxter Park Inn
Gateway Inn

Gateway Inn

2.5 out of 5
1963 Medway Road Medway ME
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Jul 28 to Jul 29
CA $141
CA $153 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very good! (458 reviews)
"Parking was great. Disappointed that the indoor pool was no longer a thing there. :-("

Reviewed on Jul 13, 2026

Gateway Inn
See all 134 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.
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Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from CA $1,145 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.

Explore a world of travel with Expedia

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