Chamberlain Vacations from $706

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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.
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was $853, price is now $706 per person
$706
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Rockland (RKD)
8.6/10 Excellent! (419 reviews)
The room and bathroom were very clean and nice showering amenities were included… I slept very well.

Reviewed on Jul 12, 2026

The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

3.5 out of 5
Price was $1,552, price is now $1,316 per person
$1,316
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Rockland (RKD)
9.2/10 Wonderful! (200 reviews)
Synday brunch was very good

Reviewed on Dec 22, 2025

Homeport Inn and Tavern

Homeport Inn and Tavern

3 out of 5
Price was $1,185, price is now $1,009 per person
$1,009
per person
Sep 27 - Oct 1
found 20 hours ago
Roundtrip flight included
Sioux Falls (FSD) to Rockland (RKD)
9.6/10 Exceptional! (296 reviews)
This place was a delight! The room was great, we loved the pool room and breakfast was simple but perfect. Staff was really friendly and helpful too when I asked for a recommendation.

Reviewed on Jul 13, 2026

Harborline Hotel

Harborline Hotel

3 out of 5
Price was $1,349, price is now $1,180 per person
$1,180
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Rockland (RKD)
7.6/10 Good! (282 reviews)
The staff were so pleasant and helpful! The location is great.

Reviewed on Jul 12, 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.
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Chamberlain Hotel Deals

Charming Cottage with Ocean Views, Wifi, and Washer and Dryer

Charming Cottage with Ocean Views, Wifi, and Washer and Dryer

Bristol ME
10/10 Exceptional! (2 reviews)
"We enjoyed a wonderful stay at this lovely cottage by the sea. Better than advertised and so convenient to the area’s attractions.We’d happily book this property again on another visit to Mid Coast Maine!"

Reviewed on Jun 17, 2026

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Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
$267 nightly
The price is $291 total per night from Jul 15 to Jul 16
$291 total
Jul 15 - Jul 16
Total with taxes and fees
8.6/10 Excellent! (1,015 reviews)
"Prime location on the water. Close to Boothbay and Coastal gardens. Amenities include kayaks, canoes, paddle boards, swimming pool, private fishing, pond, tennis courts, and hot breakfast. Rooms are newly refurbished. We really enjoyed our stay here and recommend it highly."

Reviewed on Jul 14, 2026

Ocean Gate Inn
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $169 total per night from Jul 15 to Jul 16
$169 total
Jul 15 - Jul 16
Total with taxes and fees
8/10 Very Good! (1,011 reviews)
"Clean room, excellent breakfast, clran pool"

Reviewed on Jul 14, 2026

Flagship Inn and Suites
See all 1,477 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 $706 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.