Kingston Vacation Packages

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Your Kingston Vacation

From its highlights to its hidden treasures, this city is best experienced with a Kingston vacation package. Look for places to stay in Plymouth Cultural District, which is great for dining, culture and history. Ready to venture out and explore? Plymouth Rock, Mayflower II and National Monument to the Forefathers are among the top-rated places to visit during your trip to Kingston. Expedia has what you need to escape the everyday. Tailor your vacation to Kingston to match your travel style, whatever that may be!

Top Kingston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was CA $1,077, price is now CA $764 per person
CA $764
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
The hotel grounds are extremely well maintained; the views of the water and benches to relax on are fantastic! We had a great stay with our two teenagers. It was out of the hustle and bustle of the city. A wonderful place!

Reviewed on Oct 26, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $1,539, price is now CA $982 per person
CA $982
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Excellent as always.

Reviewed on Oct 27, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was CA $4,951, price is now CA $3,321 per person
CA $3,321
per person
Nov 26 - Dec 2
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $4,902, price is now CA $3,408 per person
CA $3,408
per person
Nov 26 - Dec 2
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (465 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $1,334, price is now CA $935 per person
CA $935
per person
Jan 8 - Jan 10
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
设施很新，SPA桑拿体验特别好，晚餐气氛很棒

Reviewed on Oct 20, 2026

Ready to book your vacation to Kingston?

 

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Kingston Hotel Deals

Plymouth Bay Inn and Suites

Plymouth Bay Inn and Suites

2 out of 5
149 Main Street Kingston MA
Get rates
Plymouth Bay Inn and Suites
Garner Hotel Brockton - Boston by IHG

Garner Hotel Brockton - Boston by IHG

2.5 out of 5
405 Westgate Dr. Brockton MA
Fully refundable
The price is CA $144 per night from Nov 25 to Nov 26
CA $144
CA $161 total
Nov 25 - Nov 26
includes taxes & fees
Garner Hotel Brockton - Boston by IHG
Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree

3.5 out of 5
50 Forbes Road Braintree MA
The price is CA $158 per night from Nov 16 to Nov 17
CA $158
CA $177 total
Nov 16 - Nov 17
includes taxes & fees
Hyatt Place Boston/Braintree
See all 1,245 properties in Kingston
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

Stay near popular Kingston attractions

Grays Beach Park

8.6/10 (7 reviews)
If a restful vacation is part of your travel plans, Grays Beach Park might be the perfect place to seek out during your trip to Kingston. While you're in the area, wander around the parks.
See properties

Frequently asked questions

How much does a Kingston vacation package cost?
Offering excellent value package deals from CA $764 on Expedia, you'll be thrilled with how little a vacation to Kingston costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Kingston?
Plan your trip for the off-peak season and you're likely to get cheap Kingston vacation packages. Keep in mind that school vacation periods and major festivals and events can impact prices, so do a little research before you go.
How many days is enough for Kingston?
With about 2 days, you'll have enough time to visit popular neighbourhoods such as Plymouth Cultural District and North Plymouth during your Kingston vacation. Be sure to also add Duxbury Beach Park and Plymouth Memorial Hall to your must-see list. Up for some more adventures? Consider exploring outside of Kingston on tours and day trips.
Is it worth booking a vacation package to Kingston?
Kingston is a good vacation destination with attractions like Grays Beach Park among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Kingston vacation promises a good time for everyone.
How to find the best Kingston package deals?
Landing a cheap Kingston package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add some filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Kingston package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Kingston vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still have the freedom to create a tailored Kingston vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Kingston?
Land incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Kingston adventure.
How to plan a trip to Kingston?

  1. Choose your dates: The things you plan to do in Kingston and your preferred season can help you decide when to get away.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to flights and experiences. Your accommodations will likely be the largest expense during your trip to Kingston.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you want to experience in Kingston. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Kingston vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.