Rockport Vacation Packages

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Your Rockport Vacation

Book a Rockport vacation package and get ready to experience the highlights of this city. Think about staying in the neighborhood of Great Neck, which is great for walking, nature and views. Cape Ann, Good Harbor Beach and Wingaersheek Beach are just some of the many sights worth checking out during your trip to Rockport. Whoever you're heading away with and whatever you plan to spend, your dream Rockport vacation is only clicks away with Expedia.

Top Rockport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sesuit Harbor House

Sesuit Harbor House

CA $946
per person
Sep 10 - Sep 13
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (196 reviews)
Wonderful stay and would stay again

Reviewed on Aug 10, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
CA $2,525
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (475 reviews)
Overrated

Reviewed on Aug 10, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
CA $1,967
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,298 reviews)
The Mansion at Ocean Edge

The Mansion at Ocean Edge

CA $2,261
per person
Sep 10 - Sep 13
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (1,000 reviews)
We had a really nice time. We are a family of 5 with tweens. We stayed at the mansion. Pros: - the beach and the beach staff were lovely. the beach is just so cool. very clean. kids had fun with other kids, going out on the flats, playing with the hermit crabs, and wading in the water. as a parent i appreciated not fearing they were going to drown or get pulled by the waves (it was very calm). - the front lawn. kids enjoyed this during the evenings. it was a nice wat to unwind and let the kids run and play games. - the golf. my kids and husband enjoyed playing 18 and 9 holes. We also went over one evening and just used the range for an hour or so. very friendly staff and a very nice course. The cons - It did not have a high end feel to it. we were checked in and that was it. not a big deal, but it was touted as high end. I wouldn't have had that expectation otherwise. - the room air conditioning - the room itself was spacious and felt clean. the air conditioning was like a monster. it was one that came on and then turned off until the room got hot and then kicked back on. it literally woke us up every night multiple times because it was so loud - like an autobody shop or monster screeching. - inflated prices. I expect this because we're at a nice resort and a lot goes into that. but the prices were very elevated. $26 pizza on the lawn and a glass of wine and water was $30. if you're used to city/resort pricing this won't surprise you. Overall - It was a solid 'B' stay

Reviewed on Aug 11, 2026

The Charles Hotel

The Charles Hotel

West Cambridge
CA $1,637
per person
Sep 24 - Sep 27
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,006 reviews)

Rockport Beach Vacation

There's nothing like a Rockport vacation to give yourself a little boost. The soothing melody of rolling surf and the smell of clean ocean air are sure to recharge your mind and body. To be close to the city centre on your trip to Rockport, base yourself around Front Beach (0.32 kilometres away). If you're intending to stay for a bit, look into our Rockport packages. Not only can you save some cash, you'll also have other incredible beaches near you to explore, like Pebble Beach and Back Beach. We call that a win-win!

Things You Should Know About Rockport

  • Drift off to sleep to the calming sounds of the sea in one of our Rockport beach hotels. There's nothing like staying right near the water.
  • Alternatively, browse our range of private vacation homes. They're a hit with travellers planning a vacation in Rockport. Begin your search with Emerson Inn and The Cove at Rockport Hotel.
  • Rockport is home to approximately 5,000 people. Why not get out and mingle with some of them? It's a terrific way to pick up a bit of inside intel on the place! Also look up our Rockport things to do page.
  • After you've made some great savings by booking a Rockport vacation package, you can splurge on unforgettable travel experiences. Motif No 1, Pebble Beach and Paper House are a few attractions that should be on your itinerary.

Ready to book your vacation to Rockport?

Choose your dates

Rockport Hotel Deals

Rockport Inn And Suites

Rockport Inn And Suites

183 Main Street Rockport MA
CA $271
CA $302 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (1,553 reviews)
"Property and rooms very clean. Breakfast was continental only, no hot eggs"

Reviewed on Aug 11, 2026

Rockport Inn And Suites
The Rockport House

The Rockport House

17 Pleasant St Rockport MA
Fully refundableReserve now, pay when you stay
CA $220
CA $285 total
Sep 2 - Sep 3
includes taxes & fees
9.4/10 Exceptional! (247 reviews)
"Excellent, The hotel is well manteing, Love the house. Easy going in. I think that I did not receive the room that I booked but It's ok, everything else was perfect."

Reviewed on Aug 11, 2026

The Rockport House
The Cove at Rockport Hotel

The Cove at Rockport Hotel

1 King St Rockport MA
Fully refundableReserve now, pay when you stay
CA $299
CA $334 total
Sep 7 - Sep 8
includes taxes & fees
The Cove at Rockport Hotel
See all 1,658 properties in Rockport
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.

Stay near popular Rockport attractions

An aerial view of a coastal island with a rocky shoreline, dense green forest, and a small lake.

Cape Ann

9.4/10 (295 reviews)
Commune with nature and explore the great outdoors at Cape Ann during your travels in Rockport. While you're in the area, stroll along the seaside.
See properties
A rocky shoreline with a calm lake, surrounded by autumn-colored trees.

Halibut Point State Park

9.4/10 (90 reviews)
Commune with nature and explore the great outdoors at Halibut Point State Park during your travels in Rockport. Wander the seaside and beautiful beaches in this family-friendly area.
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An auditorium with rows of blue seats, wooden beams, and stone walls.

Shalin Liu Performance Center

9.0/10 (39 reviews)
You can get tickets for a performance at Shalin Liu Performance Center during your trip to Rockport. Wander the seaside and beautiful beaches in this family-friendly area.
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A harbor with boats, a red building, and houses along the shore.

Motif No 1

9.4/10 (103 reviews)
You can spend an afternoon browsing the exhibits at Motif No 1 during your trip to Rockport. Wander the seaside and beautiful beaches in the area.
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A crowded beach with people swimming and sunbathing, surrounded by houses and a lighthouse.

Front Beach

9.4/10 (93 reviews)
Why not spend a lazy afternoon at Front Beach during your trip to Rockport? While you're in the area, stroll along the seaside.
See properties
A coastal town with a sandy beach, rocky shoreline, and a prominent American flag.

Pebble Beach

9.2/10 (49 reviews)
Why not spend a carefree afternoon at Pebble Beach during your travels in Rockport? While you're in the area, stroll along the seaside.
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A rocky shoreline with a sailboat on the water, a tree, and houses in the background.

Back Beach

9.0/10 (26 reviews)
Why not spend a lazy afternoon at Back Beach during your trip to Rockport? While you're in the area, stroll along the seaside.
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Cape Hedge Beach

9.0/10 (6 reviews)
Why not spend a lazy afternoon at Cape Hedge Beach during your trip to Rockport? While you're in the area, stroll along the seaside.
See properties

What to do in Rockport

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Cape Ann Harbor: Self-Guided Driving Audio Tour

CA $24
per traveller
100% of travellers recommend
Cape Ann Harbor: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

CA $70
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $71
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Rockport

Frequently asked questions

How much does a Rockport vacation package cost?
You'll find cheap prices from CA $946 on Expedia for your Rockport escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Rockport costs.
What are the cheapest months to go to Rockport?
December, January and February are great times to search for cheap Rockport vacation packages. Opting to travel in less busy periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Rockport?
You can easily see all the leading attractions in Rockport in a few days, including the popular Pebble Beach. If you're after an extended Rockport vacation, look at which kind of excursions and activities are available in the area.
Is it worth booking a vacation package to Rockport?
It's no wonder a Rockport vacation is on the must-do list of many travellers. Top attractions like Cape Ann are just the beginning of what you can explore here.
How to find the best Rockport package deals?
Start your search for a Rockport package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Rockport package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Rockport adventure off to a flying start.
Is it cheaper to book a Rockport vacation as a package?
You can enjoy significant savings on your next Rockport getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a great-value 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 Rockport?
If you're considering an impromptu Rockport adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Rockport?
  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Rockport.
  2. Plan your budget wisely: As well as the price of your accommodations, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Rockport.
  3. Decide how many days away: Start by listing all the activities and sights you want to experience in Rockport. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Rockport vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.