Chester Vacations from $261

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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.

The Latest Chester vacation packages

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

The Pathmaker Hotel

2 out of 5
Price was $404, price is now $261 per person
$261
per person
Nov 21 - Nov 23
found 9 hours ago
Roundtrip flight included
Cleveland (CLE) to Bangor (BGR)
9.8/10 Exceptional! (248 reviews)
I can't say I was impressed by this hotel. The room faced the street and was extremely noisy at night. Maybe invest in more soundproof windows? For the price paid I was extremely disappointed. It was just a regular hotel room with nothing special. The only exception was the free parking. That was much appreciated. Would I choose to stay again? Probably not. Breakfast menu was very limited. Can't speak for dinner menu as we did not eat there.

Reviewed on Sep 28, 2025

The Primrose

The Primrose

3 out of 5
Price was $554, price is now $396 per person
$396
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.6/10 Exceptional! (937 reviews)
Breakfast was fantastic

Reviewed on Sep 27, 2025

Bar Harbor Condos

Bar Harbor Condos

2.5 out of 5
Price was $986, price is now $723 per person
$723
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Bangor (BGR)
10/10 Exceptional! (6 reviews)
It’s was lovely! A very special and beautiful property! Wonderful to be able to walk to dinner and shops. Unfortunately, with only a one-night stay, the late check-in (4p) and early checkout (10a) felt a bit rushed. It would be best enjoyed with more nights, or a slightly later checkout. Still an excellent place.

Reviewed on Aug 29, 2025

Hearthside Inn

Hearthside Inn

2.5 out of 5
Price was $360, price is now $265 per person
$265
per person
Nov 21 - Nov 23
found 9 hours ago
Roundtrip flight included
Cleveland (CLE) to Bangor (BGR)
9.8/10 Exceptional! (190 reviews)
Really delightful! Staff was so friendly, rooms were very cozy. I loved breakfast and afternoon tea, there was always a snack to be found.

Reviewed on Sep 27, 2025

The Inn on Mount Desert

The Inn on Mount Desert

3 out of 5
Price was $452, price is now $334 per person
$334
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.6/10 Exceptional! (1,005 reviews)
Great place to stay!

Reviewed on Sep 22, 2025

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Discover the most popular places to visit in Chester

Penobscot Valley Hospital

Though Penobscot Valley Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Lincoln while you are here.

Penobscot Valley Hospital

Jato Highlands Golf Course

Enjoy a round of golf in Lincoln at Jato Highlands Golf Course. While you're in the area, stroll along the marina.

Jato Highlands Golf Course

Chester Hotel Deals

Cabin on the water!

Cabin on the water!

Chester
9.2/10 Wonderful! (27 reviews)
"This is the second time my friends and I stayed here. It is a great place and the hosts are fantastic."

Reviewed on Aug 24, 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
$145 nightly
The price is $158 total per night from Oct 30 to Oct 31
$158 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (505 reviews)
"The location was great to get to Baxter State Park for hiking. We had everything we needed for the last night of our two week adventure through Acadia and up into Canada and back to Bangor. The property was a tad outdated but very clean. I would stay again."

Reviewed on Sep 24, 2025

Baxter Park Inn
Gateway Inn

Gateway Inn

2.5 out of 5
1963 Medway Road, Medway, ME
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $109 total per night from Oct 5 to Oct 6
$109 total
Oct 5 - Oct 6
Total with taxes and fees
8.2/10 Very Good! (403 reviews)
"The place is quiet with a great view on the back. They are in the middle of renovation and most of the amenities are great. There's a refrigerator and microwave in the room which is also great. Recommend this place for staying."

Reviewed on Sep 20, 2025

Gateway Inn
See all 108 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?
You can pick up a vacation package to this top destination from $261 on Expedia. However, how much your vacation to Chester costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chester?
July, September and December are great times to look for cheap Chester vacation packages. Opting to travel in quieter months means you can generally find better prices on flights and accommodations.
How many days is enough for Chester?
The ideal length of your Chester vacation depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to tick off all the main sights and discover some hidden treasures along the way.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Chester package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester escape off to a flying start.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can personalize your Chester escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Chester?
If you're planning a spontaneous Chester adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Chester trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.