Chamberlain Vacation Packages

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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.

Top Chamberlain Vacation Deals

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 CA $1,158, price is now CA $1,071 per person
CA $1,071
per person
Aug 17 - Aug 20
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rockland (RKD)
8.6/10 Excellent! (417 reviews)
Ok, nice view, horrible coffee, no windows, no screen on door, door didn't fully close, would not recommend

Reviewed on Jun 30, 2026

Harborline Hotel

Harborline Hotel

3 out of 5
Price was CA $1,222, price is now CA $1,105 per person
CA $1,105
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Rockland (RKD)
7.6/10 Good! (274 reviews)
There was little to no hot water during our stay. The front desk staff assured us a manager would be in touch, but that never happened.

Reviewed on Jun 28, 2026

Glen Cove Inn & Suites

Glen Cove Inn & Suites

2.5 out of 5
Price was CA $1,152, price is now CA $1,086 per person
CA $1,086
per person
Aug 17 - Aug 20
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rockland (RKD)
9.4/10 Exceptional! (1,011 reviews)
Have stayed twice now at Glen Cove Inn with my family and once again we enjoyed every minute of it. The staff is super friendly. Our room was spotless and comfortable. The pool was clean and well taken care off. The breakfast on the deck was really great with a nice variety to choose from and the coffee was nice and hot. We will definitely stay again in the future.

Reviewed on Jun 29, 2026

The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

3.5 out of 5
Price was CA $1,658, price is now CA $1,613 per person
CA $1,613
per person
Aug 17 - Aug 20
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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 CA $1,248, price is now CA $1,222 per person
CA $1,222
per person
Aug 17 - Aug 20
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rockland (RKD)
9.6/10 Exceptional! (295 reviews)
We could not have been happier with our recent 3-day stay at the HomePort Inn in Searsport, Maine. We knew that this was a good location for what we wanted to do... Exploratory trips to places like Camden and Castine. But what we were not prepared for, especially for the price quoted, was the luxury of the rooms and the high quality of the entire facility. Innkeepers Allison and Arno are lovely. The downstairs tavern was a perfect place for dinner one night, as well as a cocktail. This is a lovely old sea captain's mansion with high ceilings and beautiful appointments. Lots of public rooms downstairs, including a billiard table and a kind of game room library. Breakfast was great and offered on a long, lovely glassed-in porch with a view out too beautiful garden with flowering bushes and shrubs. The ocean is a short walk down a quiet side street. A walk of several blocks brings you into the downtown which has a couple of very good restaurants. Honestly we could have hung out here and never left the property, but we had lots to do and see. We hope to come back. We cannot recommend this place more highly.

Reviewed on Jun 27, 2026

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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! (1 review)
A True Seaside Delight!
"We had the best week at Sea Breeze in our first trip to Maine! After a long drive, we were stunned to turn the corner to find our home overlooking a gorgeous seaside, situated on a quiet, walkable, friendly street. When we stepped inside, we found the house to be a clean, cozy, and quiet haven that ..."

Reviewed on Aug 4, 2025

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Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
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
The price is CA $216 per night from Jul 9 to Jul 10
CA $216
CA $294 total
Jul 9 - Jul 10
includes taxes & fees
8/10 Very good! (1,002 reviews)
"We stayed overnight and found the staff to be very helpful, the room clean and spacious, and the complementary breakfast buffet was very good."

Reviewed on Jun 29, 2026

Flagship Inn and Suites
Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
The price is CA $360 per night from Jul 14 to Jul 15
CA $360
CA $413 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Ok"

Reviewed on Jun 30, 2026

Ocean Gate Inn
See all 1,293 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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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

Frequently asked questions

How much does a Chamberlain vacation package cost?
You can grab a vacation package to this top destination from CA $1,071 on Expedia. However, how much your vacation to Chamberlain costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chamberlain?
If you're hoping to snag a cheap Chamberlain vacation package, consider travelling in January, February and March. You'll generally find better rates on accommodations and flights during these months — ideal for budget-conscious travellers.
How many days is enough for Chamberlain?
The ideal length of your Chamberlain vacation depends on what you'd like to see. Usually, a handful of days to a week will give you time to hit all the leading sights and explore some hidden treasures along the way.
How to find the best Chamberlain package deals?
Bagging a cheap Chamberlain package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Chamberlain package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Chamberlain vacation as a package?
You can enjoy significant savings on your next Chamberlain getaway by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chamberlain?
If you have your Chamberlain vacation dates locked in, book as early as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Chamberlain?

  1. Choose when to go: Check your schedule and get packing. Your preferred time of year and the activities on offer will also help you decide when to visit Chamberlain.
  2. Plan your budget wisely: In addition to the cost of your stay, you should factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Chamberlain.
  3. Set the duration of your trip: Start by listing all the activities and sights you'd like to get to in Chamberlain. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Chamberlain vacation package that brings all your bookings together.

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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.