Kittery Vacation Packages

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Your Kittery Vacation

With one of our vacation packages to Kittery, you'll find limitless opportunities for adventure and relaxation. There's tons to enjoy, including its coastal scenery and rich history. Love to start exploring your surroundings? Kittery Premium Outlets, York Harbor Beach and The Kittery Outlets are three of the top places to visit during your trip to Kittery. Browse Expedia's wide range of travel options and start planning your ultimate vacation to Kittery now.

Top Kittery 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 $1,008, price is now CA $536 per person
CA $536
per person
Nov 1 - Nov 3
found 8 hours 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 $3,757, price is now CA $2,202 per person
CA $2,202
per person
Oct 23 - Oct 27
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,269, price is now CA $2,097 per person
CA $2,097
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Loved everything about it. There wasn’t anything that felt uncomfortable and there was so much that was impressive.

Reviewed on Aug. 21, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,455, price is now CA $967 per person
CA $967
per person
Nov 2 - Nov 6
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Great Experience at a great location

Reviewed on Aug. 21, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $2,825, price is now CA $1,908 per person
CA $1,908
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (441 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on Aug. 16, 2025

Ready to book your vacation to Kittery?

 

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Kittery Hotel Deals

Coachman Inn

Coachman Inn

2.5 out of 5
380 US Route 1, Kittery, ME
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Aug 26 to Aug 27
CA $161
CA $180 total
Aug 26 - Aug 27
includes taxes & fees
7.6/10 Good! (1,011 reviews)
"Parking very close. Food was light must to have to get there before 8:30 am."

Reviewed on Aug. 17, 2025

Coachman Inn
Hampton Inn & Suites Kittery-Portsmouth

Hampton Inn & Suites Kittery-Portsmouth

2.5 out of 5
275 US Route 1, Kittery, ME
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Sep 14 to Sep 15
CA $246
CA $268 total
Sep 14 - Sep 15
includes taxes & fees
9.2/10 Wonderful! (964 reviews)
"Good location and comfortable beds. We liked the breakfast options, better than most. Front desk was helpful. It room service was poor."

Reviewed on Aug. 16, 2025

Hampton Inn & Suites Kittery-Portsmouth
Ogunquit - The Milestone

Ogunquit - The Milestone

2 out of 5
687 Main Street, Ogunquit, ME
The price is CA $129 per night from Sep 7 to Sep 8
CA $129
CA $140 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (1,123 reviews)
"Property is somewhat dated"

Reviewed on Aug. 20, 2025

Ogunquit - The Milestone
See all 2,841 properties in Kittery
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
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Discover the most popular places to visit in Kittery

Kittery Premium Outlets

Kittery Premium Outlets

During your trip to Kittery, you can enjoy retail therapy at Kittery Premium Outlets. Wander the seaside and beautiful beaches in the area.

Kittery Premium Outlets

What to do in Kittery

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

Frequently asked questions

How much does a Kittery vacation package cost?
Offering great value package deals from CA $536 on Expedia, you'll be surprised at how little a vacation to Kittery costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Kittery?
December, January and February are great times to look for cheap Kittery vacation packages. Choosing to travel in quieter months means you can typically find reduced prices on flights and accommodations.
How many days is enough for Kittery?
With around 2 days, you'll have enough time to enjoy popular neighbourhoods like Pease and South Eliot during your Kittery vacation. Make sure to also add York Harbour Beach and Strawbery Banke Museum to your sightseeing list. Looking for more adventures? Consider exploring outside of Kittery on day trips and tours.
Is it worth booking a vacation package to Kittery?
Whether you want to visit top attractions like Kittery Premium Outlets and Yummies Candy and Nuts on your Kittery vacation, or coming for its great coastal beaches, walking trails and culture, there's something for everyone here. With so much to do, you'll soon find out why so many visitors think Kittery is a good vacation destination.
How to find the best Kittery package deals?
Start your search for a Kittery package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Kittery package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Kittery escape off to a flying start.
Is it cheaper to book a Kittery vacation as a package?
You can enjoy significant savings on your Kittery escape by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Kittery?
If you're planning a spur-of-the-moment Kittery adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Kittery?

  1. Pick your travel dates: The things you plan to do in Kittery and your preferred season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will likely be the largest expense during your trip to Kittery.
  3. Decide how long to go away for: Now that you're up to speed on Kittery, you can figure out the right length of your vacation. Pull together a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Kittery vacation package.

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