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 $1,931, price is now CA $816 per person
CA $816
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,196, price is now CA $1,272 per person
CA $1,272
per person
Jan 21 - Jan 24
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $1,982, price is now CA $1,354 per person
CA $1,354
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,354 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,424, price is now CA $1,664 per person
CA $1,664
per person
Dec 30 - Jan 2
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was CA $1,590, price is now CA $1,138 per person
CA $1,138
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

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 $106 per night from Nov 2 to Nov 3
CA $106
CA $120 total
Nov 2 - Nov 3
includes taxes & fees
Coachman Inn
Kittery Inn and Suites

Kittery Inn and Suites

2.5 out of 5
70 US Route 1 Bypass Kittery ME
Fully refundableReserve now, pay when you stay
The price is CA $101 per night from Nov 4 to Nov 5
CA $101
CA $110 total
Nov 4 - Nov 5
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"We enjoyed our overnight stay and we were pleasantly surprised by how cute the place was. And breakfast was just lovely."

Reviewed on Oct 29, 2026

Kittery Inn and Suites
Home2 Suites By Hilton Kittery

Home2 Suites By Hilton Kittery

3 out of 5
139 Old Post Road Kittery ME
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Nov 5 to Nov 6
CA $165
CA $180 total
Nov 5 - Nov 6
includes taxes & fees
9.4/10 Exceptional! (255 reviews)
"Great location we loved it there"

Reviewed on Oct 29, 2026

Home2 Suites By Hilton Kittery
See all 2,921 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.
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Stay near popular Kittery attractions

A sign for Outlets at Kittery Customer Service Center with a flag.

Kittery Premium Outlets

8.6/10 (1,419 reviews)
During your trip to Kittery, you can enjoy retail therapy at Kittery Premium Outlets. Wander the seaside and beautiful beaches in the area.
See properties

What to do in Kittery

Nature Guided Bike Tour: NH Greenway-Fall Foliage Bike Tour

Tour the Fall Foliage on the NH Greenway - Autumn Colors + Nature

CA $106
per adult
100% of travellers recommend
Tour the Fall Foliage on the NH Greenway - Autumn Colors + Nature
See all activities in Kittery

Frequently asked questions

How much does a Kittery vacation package cost?
Offering great value package deals from CA $816 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.

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