Kittery Point Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Kittery Point Vacation

There's no better way to travel than with one of our vacation packages to Kittery Point. The coastal scenery and rich history are two of the many reasons to stay in this captivating city. A trip to Kittery Point is an ideal opportunity to sightsee. Check out big-name attractions such as Kittery Premium Outlets, York Harbor Beach and Kittery Historical and Naval Museum. Expedia can help you escape the everyday. Tailor your vacation to Kittery Point to suit your style of travel, whatever that may be.

Top Kittery Point Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,004, price is now CA $517 per person
CA $517
per person
Oct 28 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,679, price is now CA $1,464 per person
CA $1,464
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
Lovely property and staff. Great location and spa. Will return!

Reviewed on Aug. 26, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,625, price is now CA $956 per person
CA $956
per person
Oct 31 - Nov 2
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (482 reviews)
Love the Street Bar!

Reviewed on Aug. 25, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Price was CA $1,341, price is now CA $844 per person
CA $844
per person
Sep 27 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
A simple but lovely place to stay!

Reviewed on Aug. 25, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,976, price is now CA $1,278 per person
CA $1,278
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug. 24, 2025

Ready to book your vacation to Kittery Point?

 

Choose your dates

Kittery Point Hotel Deals

Anchor Inn and Cottages Wells-Ogunquit

Anchor Inn and Cottages Wells-Ogunquit

2.5 out of 5
424 Post Rd, Wells, ME
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Sep 1 to Sep 2
CA $130
CA $155 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"The lg two bedroom cottage was spacious and clean. They had everything you would need for a long stay. Will definately go back."

Reviewed on Aug. 25, 2025

Anchor Inn and Cottages Wells-Ogunquit
Ogunquit - The Milestone

Ogunquit - The Milestone

2 out of 5
687 Main Street, Ogunquit, ME
The price is CA $128 per night from Sep 1 to Sep 2
CA $128
CA $139 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,130 reviews)
"Great location"

Reviewed on Aug. 24, 2025

Ogunquit - The Milestone
Ashworth by the Sea

Ashworth by the Sea

3 out of 5
295 Ocean Blvd, Hampton, NH
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Sep 9 to Sep 10
CA $239
CA $297 total
Sep 9 - Sep 10
includes taxes & fees
Ashworth by the Sea
See all 2,950 properties in Kittery 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
Beach Vacations
Family Vacations
Family Vacations

What to do in Kittery Point

Guide Cassandra sharing the highlights of the magnificently preserved exterior of the Rockingham. Learn the history of the building & its role at the center of Portsmouth life through the centuries.

Historical Tastings at the Iconic Rockingham

CA $110
per adult
Historical Tastings at the Iconic Rockingham
See all activities in Kittery Point

Frequently asked questions

How much does a Kittery Point vacation package cost?
Offering excellent value package deals from CA $517 on Expedia, you'll be thrilled with how little a vacation to Kittery Point costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Kittery Point?
January, February and March are great times to search for cheap Kittery Point vacation packages. Opting to travel in quieter periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Kittery Point?
Typically, a handful of days is enough for a Kittery Point vacation. With a well-planned itinerary, you can check out all the leading attractions including York Harbour Beach, as well as explore some hidden treasures along the way.
How to find the best Kittery Point package deals?
Bagging a cheap Kittery Point package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Kittery Point package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Kittery Point vacation as a package?
You can enjoy significant savings on your Kittery Point retreat by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Kittery Point?
Score amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Kittery Point getaway.
How to plan a trip to Kittery Point?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Kittery Point.
  2. Set your budget: Factor in expenses like flights, meals and transportation when working out how much to save for your trip to Kittery Point. Then, pick a property that suits your budget, whether that's an economical stay or a more upscale getaway.
  3. Work out your trip length: Consider how much time you want to spend discovering Kittery Point. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the right Kittery Point vacation package for you.

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