Deals on vacations and trips to Rockland

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Rockland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Save 100% on your flight
Price was $870, price is now $583 per person
$583
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free aparthotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,596, price is now $1,569 per person
$1,569
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,368, price is now $1,597 per person
$1,597
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,562, price is now $1,746 per person
$1,746
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.
The Highliner Hotel

The Highliner Hotel

2 out of 5
Downtown Gloucester
Save 100% on your flight
Price was $2,363, price is now $1,615 per person
$1,615
per person
Sep 12 - Sep 18
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features free WiFi in public areas, express check-out, and concierge services. A virtual front desk are provided for your convenience.

Top Rockland hotels deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $181 total per night
$181 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Free WiFi
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
$219 nightly
The price is $254 total per night
$254 total
Jul 26 - Jul 27
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the steam room, bar/lounge, and concierge services.
Pool
Pet friendly
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $185 total per night
$185 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.
Pet friendly
Free WiFi
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$258 nightly
The price is $301 total per night
$301 total
Jul 26 - Jul 27
Total with taxes and fees
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.
Pool
Hot Tub
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$249 nightly
The price is $290 total per night
$290 total
Jul 26 - Jul 27
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.
Free WiFi
Restaurant
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Free Cancellation
Reserve now, pay when you stay
$455 nightly
The price is $530 total per night
$530 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
Pool
Pet friendly
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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 Rockland attractions

Rockland Ice Rink

8.6/10 (12 reviews)
Enjoy an outing to Rockland Ice Rink during your stay in Rockland. Stroll along the area's beautiful beaches, or simply savor its top-notch restaurants.
See properties

Frequently asked questions

How much are vacation packages to Rockland?
With vacation packages available from as low as $583, it's not necessary to wipe out your bank balance to travel to Rockland. Travelocity is here to help. Bundle up experiences, flights and hotels into a convenient package and land serious discounts. The more you book, the more you save.
How long should my Rockland vacation be?
On average, travelers spend 2 nights in Rockland. However, that might not be enough time for you. If you aim to see some of the area's hidden gems, why not add a few more nights to your itinerary?
Where can I get the best vacation package deals for Rockland?
No matter your adventure, Travelocity can help you get an unbeatable Rockland package deal. The only thing you need to do is mix and match from our 400 air carriers and 1,000,000 properties worldwide.
Why should I book my Rockland vacation bundle via Travelocity?
From enticing destinations to fun experiences, we have everything you need to satisfy your travel desires. Our friendly 24/7 customer support will also ensure you're being well taken care of while you're on your getaway. And don't panic if you spot a better price on your reservation, we'll match it. That's our Price Match Guarantee.
Can I save on my Rockland car rental if I combine it with a hotel or flight?
Combining your car, flight and hotel into a Rockland vacation package is a surefire way to score the best deal. Plus, having your own set of wheels gives you absolute freedom to make your way to all those big sights you're hoping to check out. Located 120 mi from Rockland, Yale University is one attraction that should be on your must-do list. Buckle up and make a day trip of it.
Which airport is best for Rockland?
For many travelers, heading to Rockland means going through Logan Intl. Airport (BOS). This popular airport sits 17 mi north of the city center. You could also fly into T.F. Green Airport (PVD) (40 mi away from central Rockland) or Manchester-Boston Regional Airport (MHT) (60 mi away from central Rockland).
What is there to do in Rockland?
You'll notice a particular magic in the air as you stroll the streets of Rockland. Rockland Ice Rink and Rockland Golf Course are just a couple of renowned sights that make this city so popular, so add them to your travel itinerary.
Where should I stay when visiting Rockland?
If you're looking for a place to lay your head, consider the Comfort Inn Rockland - Boston. It's the top pick for many travelers.

Photos of local treasures

Browse Rockland vacation photos for more inspiration

A calm sea with multiple sailboats anchored, a distant ship, and a hazy shoreline.
A stone building with a red roof and a large red water wheel.
A stone building with a red water wheel and a waterfall, surrounded by autumn-colored trees.
A weathered boat with a rope and a wooden oar.