Cliff Vacation Packages

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Top Holiday Package Deals in Cliff

Price found within the past 48 hours. Click for updated prices.
Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $881, price is now CA $589 per person
CA $589
per person
Oct 16 - Oct 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (30 reviews)
Very impressed! Very clean, friendly staff, felt safe, the room was far bigger than expected, I’ll be back!

Reviewed on Sep. 1, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,770, price is now CA $1,955 per person
CA $1,955
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great harbor views! Room service was superb as well. Everyday we came back to an organized room and sometimes sweets, creams. The reception desk was also good in answering any questions. Excellent location. Would stay again.

Reviewed on Sep. 3, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,572, price is now CA $1,444 per person
CA $1,444
per person
Nov 5 - Nov 8
just found
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep. 2, 2025

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was CA $1,510, price is now CA $1,001 per person
CA $1,001
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,140 reviews)
It was a great experience. A bit small for four people in one room. But we made due.

Reviewed on Sep. 2, 2025

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
Price was CA $2,134, price is now CA $1,420 per person
CA $1,420
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,001 reviews)
Rooms are very small, restaurant bar was just below our room and open til 1am-very loud, restaurant for breakfast has very limited menu and coffee is terrible.

Reviewed on Sep. 1, 2025

Where to stay in Cliff

Find the best Cliff areas and neighborhoods for the activities you enjoy most. Learn more about Cliff
Nantucket which includes boating, a marina and a bay or harbour

Nantucket Town

6 out of top 10 points of interest in this area
5/5(2 area reviews)

Discover the charm of Nantucket, a historic New England seaport town, with its museums like the Nantucket Whaling Museum and picturesque landscapes. Enjoy local shops, restaurants, and explore key localities such as Surfside and Siasconset.

Find hotels in Nantucket Town

Cliff Hotel Deals

Life House, Nantucket

Life House, Nantucket

3.5 out of 5
10 Cliff Road, Nantucket, MA
The price is CA $410 per night from Oct 1 to Oct 2
CA $410
CA $481 total
Oct 1 - Oct 2
includes taxes & fees
Life House, Nantucket
Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane, Nantucket, MA
The price is CA $392 per night from Oct 2 to Oct 3
CA $392
CA $438 total
Oct 2 - Oct 3
includes taxes & fees
Nantucket Inn
The Beachside

The Beachside

4 out of 5
30 North Beach Street, Nantucket, MA
The price is CA $502 per night from Oct 2 to Oct 3
CA $502
CA $589 total
Oct 2 - Oct 3
includes taxes & fees
The Beachside
See all 865 properties in Cliff
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cliff vacation package cost?
Live it up in Cliff from as little as CA $589. We offer a great selection of rental cars, hotels and flights to suit every budget and style. You can score even better deals when you add some activities or tours to your vacation package.
How do I get a cheap travel package to Cliff?
Booking a Cliff vacation package with Expedia is an easy way to save. We offer access to over 550 airlines and 1,000,000 hotel options globally. With such a broad range to pick from, you'll have no issues creating your ideal escape.
Where should I stay in Cliff?
Stay where the action is. Many visitors favor hotels around popular sights, like Jetties Beach, Nantucket Ferry Terminal and Cisco Beach.
What are the top hotels in Cliff?
Get your escape off to an excellent start by staying at Prestigeous Cliff Road Location W. It's one of most popular hotels in Cliff. Another top option is Life House, Nantucket.
How far in advance should I book my Cliff vacation?
To score cheap prices, book as soon as you can. Airlines generally release flight tickets, along with some of the lowest fares, nearly a year ahead of time. Hotels, car rental and activities should also be booked early to avoid disappointment. If you're in need of a last-minute getaway in Cliff, there are always plenty of great deals on Expedia. Book your escape today!
What does an Expedia Cliff travel package include?
Flights, rental cars and hotels, or any combination of them — it's your choice. Whether you're exploring Cliff with the entire family or traveling with your friends, there's a package to fit your budget and style. Once you've made your booking, why not add on one or two tours or activities?
What should I know before booking a Cliff travel package?
Whether it's adventure or relaxation you're seeking, a Cliff vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Cliff Expedia vacation package?
You can, and with over 550 airlines to select from across the globe, you've got lots of choice. Search the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Cliff vacation package?
Whether it's your flight or hotel, you can cancel and rebook it. Locked in your Cliff vacation package in the last 24 hours? You may be able to make any changes for free. If it's been longer than that, you may incur a charge from your airline, hotel or car rental company. For further information, take a look at our Customer Service Portal. We'll help you every step of the way.

Discover the most popular places to visit in Cliff

Madaket Beach

Madaket Beach

If a restful vacation is part of your travel plans, Madaket Beach might be the perfect place to seek out during your trip to Nantucket.

Madaket Beach
Jetties Beach

Jetties Beach

4/5(1 review)

Why not spend a carefree afternoon at Jetties Beach during your travels in Nantucket?

Jetties Beach
Siasconet Beach

Siasconet Beach

If a restful vacation is part of your travel plans, Siasconet Beach might be the perfect place to seek out during your trip to Siasconset.

Siasconet Beach

Things to do

Private Professional Photoshoot in Nantucket

Private Professional Photoshoot in Nantucket

CA $449
per adult
Private Professional Photoshoot in Nantucket
See all activities in Nantucket
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.