Cliff Vacations from $392

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Your Cliff Vacation

Book a Cliff vacation package and immerse yourself in the way of life and rhythm of this vibrant neighborhood. With all your travel plans worked out, the only thing you need to worry about here is living your best life. Not sure what to do during your trip to Cliff? Nearby attractions like Cisco Beach, Jetties Beach and Whaling Museum are good places to start. No matter what your ideal Cliff vacation looks like, you can make it a reality with Expedia.

The Latest Cliff Vacation Packages

Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $662, price is now $392 per person
$392
per person
Feb 26 - Mar 3
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Nice room with separate living room. We enjoyed the gym, pool and hot tub. We stayed on second floor and there is only one elevator, so you have to wait sometime. I wish there is stairs to walk down.

Reviewed on Jan 6, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,144, price is now $454 per person
$454
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,973, price is now $1,149 per person
$1,149
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
I had a blast at Raffles

Reviewed on Jan 12, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,236, price is now $771 per person
$771
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Location was perfect, staff was wonderful and the foyer and lobby and the bar/ restaurant was amazing! The guest rooms were good, bed was comfortable and room was immaculate! My only complaint would be the water pressure in the shower was weak! Other than that a very good experience!

Reviewed on Jan 13, 2026

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $642, price is now $406 per person
$406
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,241 reviews)
The place was so clean and well organized

Reviewed on Jan 13, 2026

Where to stay in Cliff

Find the best Cliff areas and neighborhoods for the activities you enjoy most. Learn more about Cliff
From the dock.

Nantucket Town

6 out of top 10 points of interest in this area
5/5(50 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
8/10 Very Good! (65 reviews)
Nice location and Allison the host was wonderful. It is an older house though lots of character and the room was very nice. The refrigerator needs to be replaced and the ice box was frosted over. Otherwise it was a very nice stay.

Reviewed on Oct 10, 2025

Get rates
Life House, Nantucket
Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
$119 nightly
The price is $133 total per night from Jan 29 to Jan 30
$133 total
Jan 29 - Jan 30
Total with taxes and fees
9/10 Wonderful! (643 reviews)
Great hotel , indoor pool and nice staff

Reviewed on Dec 28, 2025

Nantucket Inn
Hotel Pippa

Hotel Pippa

3.5 out of 5
5 Chestnut Street Nantucket MA
$189 nightly
The price is $211 total per night from Jan 15 to Jan 16
$211 total
Jan 15 - Jan 16
Total with taxes and fees
9.2/10 Wonderful! (260 reviews)
Nice friendly hostess and very clean

Reviewed on Dec 20, 2025

Hotel Pippa
See all 1,015 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Cliff

AXE420 Sunbathers and dune landscape on Surfside Beach on the seaward coast of the island of Nantucket, Massachusetts, New England, USA

Surfside Beach

Why not spend a carefree afternoon at Surfside Beach during your travels in Nantucket? Discover the museums in this walkable area, or seek out its biking trails.

Surfside Beach
Weathered Houses and Drift Fence, Madaket Beach, Nantucket Island; Shutterstock ID 695324335; Purchase Order: -

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
D3RPKW Wooden steps leading down to Jetties beach, Nantucket Island, MA

Jetties Beach

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

Jetties Beach

Things to do

Private Professional Photoshoot in Nantucket

Private Professional Photoshoot in Nantucket

$328
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.