Kittery Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,105, price is now CA $772 per person
CA $772
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (193 reviews)
Loved it here! Everyone was friendly and helpful.

Reviewed on Jul 1, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,260, price is now CA $1,427 per person
CA $1,427
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Price was CA $1,698, price is now CA $1,134 per person
CA $1,134
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (467 reviews)
A beautiful, convenient, affordable place, especially for someone just in transit between airports.

Reviewed on Jun 30, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,658, price is now CA $1,134 per person
CA $1,134
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,000 reviews)
Wonderful service and spacious family room. No complaints!

Reviewed on Jun 28, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,949, price is now CA $2,097 per person
CA $2,097
per person
Aug 4 - Aug 7
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Ready to book your vacation to Kittery?

 

Choose your dates

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 $242 per night from Jul 5 to Jul 6
CA $242
CA $263 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (124 reviews)
"Great hôtel."

Reviewed on Jun 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 $243 per night from Jul 12 to Jul 13
CA $243
CA $265 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Clean and comfortable room. Checked in early with no problem. Front desk very helpful and friendly I stayed here once before and had a great experience."

Reviewed on Jun 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 $152 per night from Jul 2 to Jul 3
CA $152
CA $170 total
Jul 2 - Jul 3
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Average cleanliness .. bathtub had someone else’s hair in it / shower curtain was moldy / floor carpet was musty / cost for the night was certainly NOT budget!!"

Reviewed on Jun 29, 2026

Coachman Inn
See all 2,942 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

Rise and Shine Guided Paddleboard Yoga Class in Rye

Rise and Shine Guided Paddleboard Yoga Class in Rye

CA $51
per adult
Rise and Shine Guided Paddleboard Yoga Class in Rye
Nature Bike Tour: Biking Adventure Along The NH Greenway Rail

Nature Bike Tour: Biking Adventure Along The NH Greenway Rail

CA $111
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 $270
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 $772 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.

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.