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 $1,209, price is now CA $657 per person
CA $657
per person
Sep 7 - Sep 9
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,395, price is now CA $1,473 per person
CA $1,473
per person
Sep 4 - Sep 7
found 16 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
A fantastic stay. The room was so comfortable and cleaned carefully every day. Room overlooked the harbor and the activity of boats but it was peaceful and calm. We LOVED our stay and definitely will return when we’re back in Bean Town!

Reviewed on Jul 30, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,465, price is now CA $1,683 per person
CA $1,683
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)

The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was CA $2,044, price is now CA $1,395 per person
CA $1,395
per person
Sep 23 - Sep 27
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,007 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,620, price is now CA $2,478 per person
CA $2,478
per person
Oct 21 - Oct 24
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
Amazing hotel Amazing facility and Amazing team. Clean excellent location and very friendly

Reviewed on Jul 30, 2026

Ready to book your vacation to Kittery?

 

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Kittery Hotel Deals

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 $248 per night from Aug 30 to Aug 31
CA $248
CA $270 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (154 reviews)
"Excellent stay for a week with a pet. Breakfast and staff very good. Internet however was not working in room. Parking was tight and location was hard to get in and out."

Reviewed on Jul 30, 2026

Home2 Suites By Hilton Kittery
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 $217 per night from Aug 30 to Aug 31
CA $217
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Breakfast leaves a lot to be desired, including that staff's attitudes which were clearly evident as in unhappy. Otherwise, it was non descript."

Reviewed on Jul 30, 2026

Hampton Inn & Suites Kittery-Portsmouth
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 $184 per night from Aug 2 to Aug 3
CA $184
CA $205 total
Aug 2 - Aug 3
includes taxes & fees
Coachman Inn
See all 2,922 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 Bike Tour: Biking Adventure Along The NH Greenway Rail

Nature Bike Tour: Biking Adventure Along The NH Greenway Rail

CA $121
per adult
100% of travellers recommend
Nature Bike Tour: Biking Adventure Along The NH Greenway Rail
Wallis Sands

E-Bike By The Sea: Scenic Tour of Beaches, Harbors & Hidden Gems

CA $319
per adult
E-Bike By The Sea: Scenic Tour of Beaches, Harbors & Hidden Gems
See all activities in Kittery

Frequently asked questions

How much does a Kittery vacation package cost?
Offering great value package deals from CA $657 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.