Chamberlain Vacations from $479

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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.
Harborline Hotel

Harborline Hotel

3 out of 5
Price was $569, price is now $479 per person
$479
per person
Sep 25 - Sep 28
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to Rockland (RKD)
7.6/10 Good! (124 reviews)
Great location and friendly staff

Reviewed on Aug 22, 2025

Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was $616, price is now $512 per person
$512
per person
Sep 25 - Sep 28
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to Rockland (RKD)
8.4/10 Very Good! (250 reviews)
It was very hands off-- you go, retrieve your key from the lock box and let yourself in. But it is a gorgeous old building built like a fancy plantation - castle, in the middle of a small coastal town in pristine Maine, with a pool and a fitness center. I didn't realize it at first, but my room had a hallway to another living room area, with a balcony to sit and watch the sunrise from. Wow! Yeah, it's a great place.

Reviewed on Aug 14, 2025

The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

3.5 out of 5
Price was $627, price is now $551 per person
$551
per person
Oct 9 - Oct 12
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to Rockland (RKD)
9/10 Wonderful! (188 reviews)
Delightful, historical inn right next to Clark Island Preserve. Lovely wee walks on the shore and to the old quarry. Minimal light pollution at night allows for terrific stargazing. Rooms are on the small side, but thoughtfully designed. Included breakfast was delicious, with fresh made biscuits and a nice selection of offerings. Only slight negative is the slow WiFi, but maybe it's okay to take a break from streaming and read a book!

Reviewed on Jul 28, 2025

Homeport Inn and Tavern

Homeport Inn and Tavern

3 out of 5
Price was $984, price is now $883 per person
$883
per person
Oct 24 - Oct 27
found 8 hours ago
Roundtrip flight included
Cleveland (CLE) to Rockland (RKD)
9.8/10 Exceptional! (283 reviews)
This beautiful antique mansion was the perfect place to begin exploring. Convenient to many attractions. Onsite tavern was a bonus. Breakfasts were perfect.hard to find charm and great hospitality.

Reviewed on Aug 13, 2025

Glen Cove Inn & Suites

Glen Cove Inn & Suites

2.5 out of 5
Price was $958, price is now $880 per person
$880
per person
Oct 24 - Oct 27
found 13 hours ago
Roundtrip flight included
Cleveland (CLE) to Rockland (RKD)
9.4/10 Exceptional! (955 reviews)
Check-in was easy, the room was clean and included a small refrigerator and coffee maker, and the breakfast was perfect. We thoroughly enjoyed our visit and would not hesitate to stay here again.

Reviewed on Aug 20, 2025

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Discover the most popular places to visit in Chamberlain

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.

Rachel Carson Salt Pond Preserve

Chamberlain Hotel Deals

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

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

Bristol
Get rates
Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $191 total per night from Sep 1 to Sep 2
$191 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
"The property is amazing, amenities are great, the place is really relaxing, and nice views just above the ocean. We'll come back!"

Reviewed on Aug 18, 2025

Ocean Gate Resort
Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue, Boothbay Harbor, ME
$149 nightly
The price is $163 total per night from Sep 21 to Sep 22
$163 total
Sep 21 - Sep 22
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
"It was a nice place to stay! Quiet and clean. Agreeable personnel!"

Reviewed on Aug 20, 2025

Flagship Inn and Suites
See all 1,299 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.

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Frequently asked questions

How much does a Chamberlain vacation package cost?
Offering great value package deals from $479 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.