Chamberlain Vacations from $760

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Your Chamberlain Vacation

Put together a custom vacation package to Chamberlain and prepare to experience this exciting city the way you want. Consider spending time in the neighborhood of Medomak, which is great for walking and much more. Fill your days with tours of Pemaquid Point Lighthouse Park, Pemaquid Beach Park and La Verna Preserve, some of the attractions you just have to see during a trip to Chamberlain. Don't put off your visit to this destination any longer. The perfect Chamberlain vacation is just a few clicks away with Expedia.

The Latest Chamberlain vacation packages

Price found within the past 48 hours. Click for updated prices.
Homeport Inn and Tavern

Homeport Inn and Tavern

$760
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Rockland (RKD)
9.6/10 Exceptional! (302 reviews)
Elegant Ocean View Home With Breathtaking Views, Private hot tub & Large Deck

Elegant Ocean View Home With Breathtaking Views, Private hot tub & Large Deck

$4,094
per person
Nov 5 - Nov 9
found 18 hours ago
Roundtrip flight included
McAllen (MFE) to Rockland (RKD)
No reviews
Harborline Hotel

Harborline Hotel

$864
per person
Nov 5 - Nov 9
found 18 hours ago
Roundtrip flight included
McAllen (MFE) to Rockland (RKD)
7.4/10 Good! (338 reviews)
Room was clean. Staff was great! Parking was close. Breakfast was the only disappointment.

Reviewed on Aug 26, 2026

Trade Winds on the Bay

Trade Winds on the Bay

$940
per person
Nov 5 - Nov 9
found 18 hours ago
Roundtrip flight included
McAllen (MFE) to Rockland (RKD)
8.6/10 Excellent! (459 reviews)
I was so disappointed in the room that I left one night early (of just two) and ate the cost. The bed was poorly supportive and uneven. Felt like a fold out or a futon even though they were two double beds. The room was dark and sorely in need of an update. There was one soft spot in the floor under the carpet that you could feel plywood flexing unsupported, right near the bathroom sink. Neither of the bathroom sink or shower had a drain stopper. One or more of the drop ceiling tiles in the bathroom were water stained brown. My room was advertised to have no windows, except there was one window, oddly facing the hallway with a poorly covering curtain. It let so much hallway light in that several times I woke up, thinking I missed my alarm clock and the day had begun. Very disappointing, considering how highly rated this was on the Expedia site.

Reviewed on Aug 27, 2026

The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

$1,062
per person
Nov 5 - Nov 9
found 18 hours ago
Roundtrip flight included
McAllen (MFE) to Rockland (RKD)
9.2/10 Wonderful! (201 reviews)
We love the Craignair and this was our second visit. The staff are all wonderful and so accommodating. Our arrival was a bit rough because there was private event taking place, so we had to wait until the bartender found someone to check us in and then it felt a bit like we weren't supposed to be in the common areas until the event concluded. No big deal, but we might have planned differently had we known ahead of time that this was the case. Wait staff were a bit loud one night after dinner service, but quieted down when we asked. Still, I am impressed at how relaxed and homey the place feels even in high summer when tourists are everywhere. We had previously stayed in November and kind of had it to ourselves, so we were definitely spoiled by that experience, but were amazed at how peaceful it was even during the busy season. Loved hiking Craig Island and watching the birds and the waves every morning and evening from our balcony or the dining area. This place is truly a gem.

Reviewed on Aug 9, 2026

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Stay near popular Chamberlain attractions

Rachel Carson Salt Pond Preserve

Commune with nature and explore the great outdoors at Rachel Carson Salt Pond Preserve during your travels in Chamberlain. While you're in the area, stroll along the seaside.
See properties

Chamberlain Hotel Deals

Flagship Inn and Suites

Flagship Inn and Suites

200 Townsend Avenue Boothbay Harbor ME
$142 nightly
$155 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,046 reviews)
"I’ve stayed here a few times and this place is nice. The staff has always been helpful, my room always seemed clean. I haven’t tried the breakfast or used any facilities, but from what I could see, it was nice. I recommend this place, nicely located. About a 7 minute walk into town, trolley stops ..."

Reviewed on Aug 28, 2026

Flagship Inn and Suites
Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

191 Shore Road East Boothbay ME
Fully refundableReserve now, pay when you stay
$239 nightly
$261 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (622 reviews)
"Very clean and tidie! Fluffy towels! Only negative was th red coffee in the lobby, no taste and tv remote was hard to work!"

Reviewed on Aug 27, 2026

Bluebird Ocean Point Inn
Topside Inn

Topside Inn

60 McKown St Boothbay Harbor ME
Fully refundableReserve now, pay when you stay
$431 nightly
$470 total
Aug 30 - Aug 31
Total with taxes and fees
10/10 Exceptional! (153 reviews)
"Beautiful location, great breakfast, view of the Harbor was fantastic. Everything about this place was top-notch."

Reviewed on Aug 28, 2026

Topside Inn
See all 1,457 properties in Chamberlain
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.

Find the Best Chamberlain Vacation Packages

Chamberlain Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Knox County Regional Airport (RKD)
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Maine State Aquarium, Carousel Music Theater and Grimes Cove Beach

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Frequently asked questions

How much does a Chamberlain vacation package cost?
Offering great value package deals from $760 on Expedia, you'll be surprised at how little a vacation to Chamberlain costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Chamberlain?
If you're hoping to book a cheap Chamberlain vacation package, consider planning a trip in October, November and December. You'll generally find lower prices on flights and accommodations during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Chamberlain?
Generally, a handful of days is enough to check out the main sights during your Chamberlain vacation. However, if you want to have time to rest or take day trips, think about extending your trip.
How to find the best Chamberlain package deals?
Start your search for a Chamberlain package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Chamberlain package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chamberlain getaway off to a flying start.
Is it cheaper to book a Chamberlain vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Chamberlain vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chamberlain?
If you have your Chamberlain travel dates locked in, book as early as you can to score some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Chamberlain vacation packages?
Your Chamberlain trip is meant to be an escape from your daily routine, not a reason for money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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