Smith Point Vacation Packages

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Top Holiday Package Deals in Smith Point

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,765, price is now CA $1,147 per person
CA $1,147
per person
Jul 1 - Jul 5
found 18 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

Hilton Boston Park Plaza

4 out of 5
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! (3,127 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

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,579, price is now CA $1,584 per person
CA $1,584
per person
Jul 19 - Jul 24
found 12 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

Staypineapple, A Delightful Hotel, South End

3 out of 5
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

Chatham Tides

2.5 out of 5
Price was CA $2,902, price is now CA $1,982 per person
CA $1,982
per person
Jul 1 - Jul 5
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (682 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 Smith Point

Find the best Smith Point areas and neighborhoods for the activities you enjoy most. Learn more about Smith Point
Nantucket Town

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.

Find hotels in Nantucket Town

Smith Point Hotel Deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
The price is CA $250 per night from May 17 to May 18
CA $250
CA $279 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (672 reviews)
Management is great and hotel is wonderful

Reviewed on May 1, 2026

Nantucket Inn
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St. Nantucket MA
The price is CA $278 per night from May 12 to May 13
CA $278
CA $326 total
May 12 - May 13
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

Faraway Nantucket
White Elephant Hotel

White Elephant Hotel

4.5 out of 5
50 Easton Street Nantucket MA
The price is CA $536 per night from May 6 to May 7
CA $536
CA $599 total
May 6 - May 7
includes taxes & fees
9.6/10 Exceptional! (337 reviews)
Lovely harbour inn. Staff were super helpful with tips on where to visit and where to eat. Harbour view room was amazing and bed super comfortable. Missed having a bath tub but everything else perfect

Reviewed on Apr 24, 2026

White Elephant Hotel
See all 1,467 properties in Smith Point
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
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Family Vacations
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Frequently asked questions

How much does a Smith Point vacation package cost?
Explore the best of Smith Point from just CA $1,147. We offer a great selection of hotels, flights and rental cars to suit your travel style. You can pick up even better deals when you add some sightseeing activities to your package.
How do I get a cheap travel package to Smith Point?
Crafting your own Smith Point vacation package with Expedia is one of the best ways to save. We have more than 550 air carriers and 1,000,000 hotels worldwide. With such an awesome range to choose from, you'll have no difficulty creating your dream getaway.
Where should I stay in Smith Point?
With interesting attractions like Cisco Beach and Madaket Beach in this area, look for a hotel situated near either of them. Hummock Pond is another Smith Point sight that draws the crowds.
How far in advance should I book my Smith Point vacation?
It's tricky picking the best time for airfares, but we normally say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to a year in advance. If you're booking last minute, don't stress. Budget prices appear from time to time just weeks before departure dates.
What does an Expedia Smith Point travel package include?
It depends on what type of getaway you're contemplating. Smith Point vacation deals can include hotels, flights and car rentals. You can mix and match to find the package that suits your budget and style. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Smith Point travel package?
You'll score big savings when you combine your hotels, flights and rental cars into a package. Not only that, booking everything in one place simply makes planning easier. So why waste your time or money? Whether you're organizing a fancy romantic getaway or a budget solo adventure, explore our package deals today.
Can I choose my airline with a Smith Point Expedia vacation package?
You can, and with more than 550 airlines to choose from globally, you've got lots of choice. Search the available options and find out which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Smith Point vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Smith Point

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
Nantucket_CiscoBeach_6297949-3

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.

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

Jetties Beach

4/5(1 review)

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

Jetties Beach

Things to do

Nantucket Tirade Scavenger Hunt

Nutty Nantucket Scavenger Hunt

CA $40
per adult
Nutty Nantucket Scavenger Hunt
Private Vacation Photoshoot with Photographer in Nantucket

Private Vacation Photoshoot with Photographer in Nantucket

CA $869
per adult
Private Vacation Photoshoot with Photographer 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.