Rockland Vacation Packages

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Your Rockland Vacation

Get to know the scenic city of Rockland with a tailor-made Rockland vacation package and immerse yourself in all it has to offer. From its coastal scenery and rich history to its artistic creativity, prepare to be charmed by this fascinating destination. If a sightseeing tour is on the cards during your trip to Rockland, check out top attractions like Samoset Resort Golf Course, Rockland Breakwater Lighthouse and Sandy Beach. Whoever you're escaping with and whatever your bank balance, your dream Rockland vacation is just clicks away with Expedia.

Top Rockland 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 $1,021, price is now CA $879 per person
CA $879
per person
Sep 25 - Sep 30
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Rockland (RKD)
8.6/10 Excellent! (419 reviews)
I enjoyed my stay here very much, which was conveniently located near the windjammer docks which was the main reason that brought me here… staff is very courteous attentive to detail, and there is one hell of a great steamed muscle restaurant called Park Street Grille which I had to go to three times! During the time I was initially there, the main parking lot was being resurfaced, but as I didn’t need a car didn’t immediately affect me…

Reviewed on Jul 5, 2026

Rockland Beach Vacation

Get set to live out those beachy daydreams on your upcoming Rockland vacation. Enjoy a lovely walk, soak up the sweeping ocean views and pick up unique seashells on your trip to Rockland. Just 0.64 kilometres from the town centre, Sandy Beach is the place to be for many travellers. Look through our Rockland vacation deals and watch your travel budget stretch further!

Things You Should Know About Rockland

  • Spend your vacation by the water and let the stresses and strains of daily life drift away with the sea breeze. Book one of our Rockland beach hotels and indulge in a little beachside bliss.
  • Consider Rockland Harbour Hotel and 250 Main Hotel. These popular private vacation homes could just be ideal for your vacation in Rockland.
  • There are lots of activities that keep the 7,200 or so residents of Rockland busy. A quick look at our Rockland things to do page will let you in on the best of what's on offer.
  • Don't head home without swinging by Maine Coastal Islands National Wildlife Refuge Visitor Centre, Rockland Ferry Terminal and Rockland Harbour Park. With the cash you save through our Rockland vacation deals, you can see more top sights like these.

Ready to book your vacation to Rockland?

 

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Rockland Hotel Deals

Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive Rockland ME
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Jul 13 to Jul 14
CA $209
CA $249 total
Jul 13 - Jul 14
includes taxes & fees
7.6/10 Good! (286 reviews)
"Clean, reasonable size bedroom and bathroom. Excellent on-site parking. Walking or close driving distance to restaurants and museums."

Reviewed on Jul 7, 2026

Harborline Hotel
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
2 Park Dr Rockland ME
8.6/10 Excellent! (426 reviews)
"I enjoyed my stay here very much, which was conveniently located near the windjammer docks which was the main reason that brought me here… staff is very courteous attentive to detail, and there is one hell of a great steamed muscle restaurant called Park Street Grille which I had to go to three times! ..."

Reviewed on Jul 5, 2026

Get rates
Trade Winds on the Bay
Rockland Harbor Hotel

Rockland Harbor Hotel

2.5 out of 5
520 Main Street Rockland ME
Fully refundableReserve now, pay when you stay
The price is CA $297 per night from Jul 13 to Jul 14
CA $297
CA $324 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"Wonderful hotel! The staff was above and beyond courteous and helpful. The view of the harbor was beautiful. The hotel was very clean. A nice seating area with fire pit was available that we enjoyed. Highly recommend."

Reviewed on Jul 7, 2026

Rockland Harbor Hotel
See all 1,254 properties in Rockland
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 Rockland attractions

A lighthouse on a rocky breakwater with a forested hill in the background.

Rockland Breakwater Lighthouse

9.4/10 (326 reviews)
You can find out about the history of Glen Cove when you stop by Rockland Breakwater Lighthouse. While you're in the area, stroll along the waterfront.
See properties

Frequently asked questions

How much does a Rockland vacation package cost?
Offering great value package deals from CA $879 on Expedia, you'll be pleasantly surprised at how much a vacation to Rockland costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Rockland?
You're likely to find lower prices and better availability in February, March and April. Browse our cheap Rockland vacation packages and you could score some excellent off-season deals.
How many days is enough for Rockland?
Typically, a handful of days is enough to tick off the main sights during your Rockland vacation. However, if you prefer to have some time to chill out or go on day trips, think about extending your itinerary.
Is it worth booking a vacation package to Rockland?
Rockland has everything you need for a memorable getaway — festivals, dining and shopping are just the start. Whether you'd like to visit sights such as Maine Coastal Islands National Wildlife Refuge Visitor Centre and Rockland Harbour Park, or take the path less travelled, you'll have plenty to explore on your Rockland vacation.
How to find the best Rockland package deals?
Use Expedia's filter tool to help you find some great Rockland package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Rockland package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Rockland vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the freedom to create a personalized Rockland vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Rockland?
Score incredible discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Rockland vacation.
How to plan a trip to Rockland?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Rockland.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Rockland.
  3. Determine how many days away: Start by making a list of all the attractions you want to get to in Rockland. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Rockland vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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