Cliff Vacation Packages
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Top Holiday Package Deals in Cliff
Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites
Price was CA $1,765, price is now CA $1,147 per person
CA $1,147
per person
Jul 1 - Jul 5
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!
Reviewed on Sep 20, 2025
Hilton Boston Park Plaza
Bay Village
Price was CA $2,544, price is now CA $1,522 per person
CA $1,522
per person
Jun 17 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (3,107 reviews)
Everything was great except for the shower, which is too small.
Reviewed on Apr 29, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was CA $2,579, price is now CA $1,584 per person
CA $1,584
per person
Jul 19 - Jul 24
found 15 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Splendid bed and breakfast
Reviewed on Apr 29, 2026
Staypineapple, A Delightful Hotel, South End
South End
Price was CA $2,001, price is now CA $1,303 per person
CA $1,303
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,003 reviews)
I had a great experience staying at Staypineapple in the South End. The hotel has a really fun, unique vibe while still feeling clean and well put together. The rooms were cozy but thoughtfully designed, and the bed was honestly one of the most comfortable I’ve slept in.
The staff was friendly and welcoming, and the location made it easy to get around Boston and explore nearby restaurants and shops. Small touches like the complimentary coffee and overall atmosphere made the stay feel a little more special.
Would definitely stay here again and recommend it to anyone looking for something a bit different from a typical hotel.
Reviewed on Apr 30, 2026
Chatham Tides
Price was CA $2,902, price is now CA $1,982 per person
CA $1,982
per person
Jul 1 - Jul 5
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (685 reviews)
Excellent
Such a great surprise
Amazing view.
Great staff, very helpful with restaurant recommendations
We loved it
Reviewed on Apr 23, 2026
Where to stay in Cliff
Find the best Cliff areas and neighborhoods for the activities you enjoy most. Learn more about Cliff
Nantucket Town
5 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.
Cliff Hotel Deals
Life House, Nantucket
10 Cliff Road Nantucket MA
The price is CA $283 per night from May 17 to May 18
CA $283
CA $338 total
May 17 - May 18
includes taxes & fees
8.2/10 Very Good! (66 reviews)
Room was very clean and staff was helpful from beginning to end. Stayed in room 304 which was a top floor room. Second day in there was a bunch of stink bugs falling from ceiling onto the bed . I know they are harmless. Just annoying little creatures
Reviewed on Apr 27, 2026
Nantucket Inn
1 Miller Lane Nantucket MA
The price is CA $270 per night from May 26 to May 27
CA $270
CA $302 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (672 reviews)
Management is great and hotel is wonderful
Reviewed on May 1, 2026
Faraway Nantucket
29 Centre St. Nantucket MA
The price is CA $303 per night from May 7 to May 8
CA $303
CA $355 total
May 7 - May 8
includes taxes & fees
8.8/10 Excellent! (522 reviews)
I’ve stayed at this hotel twice. Beautiful place, great location. The only issue I could someone having in there are no elevators. I stayed on the third floor this time and while I didn’t mind carrying my bag, someone a little older (+60) may have an issue. Staff are willing to help if ...
Reviewed on Apr 26, 2026
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.
Frequently asked questions
Discover the most popular places to visit in Cliff
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.
Cisco Beach
If a restful vacation is part of your travel plans, Cisco Beach might be the perfect place to seek out during your trip to Nantucket. Discover the museums in this walkable area, or seek out its biking trails.
Jetties Beach
Why not spend a carefree afternoon at Jetties Beach during your travels in Nantucket?
Things to do
Private Vacation Photoshoot with Photographer in Nantucket
CA $869
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.