A marina with various boats docked at wooden piers, a bridge in the background, and a forested hillside.

Kittery Holidays from £920

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Your Kittery Holiday

With one of our holiday 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 Harbour 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 holiday to Kittery now.

Top Kittery flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 27 Jan - 2 Feb

    Eurostars The Boxer + Flight

    West End
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,635 reviews)
    Return • London (LHR) - Boston (BOS)
    LHR - BOS • Direct BOS - LHR • 1 stop
    £1,176
    £920
    per traveller
    found 1 day ago
    Eurostars The Boxer
  • 16 Jan - 21 Jan

    Boston Harbor Hotel + Flight

    North End
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    Return • London (LON) - Boston (BOS)
    LHR - BOS • Direct BOS - LHR • 1 stop
    £2,099
    £1,209
    per traveller
    found 1 hour ago
    Boston Harbor Hotel
  • 16 Jan - 21 Jan

    The Langham, Boston + Flight

    Downtown Boston
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    Return • London (LON) - Boston (BOS)
    LHR - BOS • Direct BOS - LHR • 1 stop
    £1,583
    £1,199
    per traveller
    found 1 hour ago
    The Langham, Boston
  • 27 Dec - 31 Dec

    Mandarin Oriental, Boston + Flight

    Back Bay
    4 nights
    5.0 star property
    9.4/10 - Exceptional (468 reviews)
    "Overall Excellent! clean room, very nice staff"
    Reviewed November 4, 2026
    Return • Birmingham (BHX) - Boston (BOS)
    BHX - BOS • 1 stop BOS - BHX • 1 stop
    £3,018
    £2,346
    per traveller
    found 1 day ago
    Mandarin Oriental, Boston
  • 27 Dec - 31 Dec

    The Newbury Boston + Flight

    Back Bay
    4 nights
    5.0 star property
    9.4/10 - Exceptional (749 reviews)
    Return • Birmingham (BHX) - Boston (BOS)
    BHX - BOS • 1 stop BOS - BHX • 1 stop
    £2,750
    £2,148
    per traveller
    found 1 day ago
    The Newbury Boston

Where to stay in Kittery

Find the best Kittery areas for the activities you enjoy most.

Kittery Foreside

While Kittery Foreside may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Seacoast Repertory Theatre and Prescott Park.

Discover the most popular places to visit in Kittery

Kittery Hotel Deals

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.

Frequently Asked Questions

How much does a Kittery travel package cost?

Live it up in Kittery from as little as £920. Choose from a great selection of flights, rental cars and hotels to suit your budget. You can score even better deals when you add a couple of tours or experiences to your package.

If I'm not able to travel, can I cancel my Kittery travel package?

Yes, it's possible to cancel your Kittery booking if your plans have changed. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

How do I get a cheap travel package to Kittery?

Find flights that fit your schedule, add a hotel room to your booking and watch the savings pile up with a Kittery travel package. It's that simple! From flights and hotels to rental cars and activities, Expedia is where your cheap holiday begins. And with more than 550 partner airlines and 1,000,000 properties around the globe to select from, you'll never be short of choice.

Does Expedia offer Book Now, Pay Later Kittery holidays?

We sure do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply pick the payment plan that works for you during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: If you'd like to pay for your escape across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

Where should I stay in Kittery?

A getaway to Kittery wouldn't be complete without visiting Kittery Premium Outlets, Fort McClary State Park and Yummies Candy and Nuts. Spend your evenings near these popular attractions and make sightseeing simple.

What are the top hotels in Kittery?

Gorges Grant Hotel and Anchorage Inn and Resort are among the most sought-after hotels in Kittery. Why not look up the rates and amenities at each and then decide?

How far in advance should I book my Kittery holiday?

Your best bet is to book early. Air carriers generally release flights around a year in advance, and this is a fantastic opportunity to score some of the cheapest prices. Boss just told you to use up all your holiday days next month? That's fine too — Expedia are never short on fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.

What does an Expedia Kittery travel package include?

Rental cars, hotels and flights — we've got them all. With Expedia, you can create your Kittery package however you want. All you have to do is determine just what you need. Once you've made your booking, you can add on extras like activities and experiences. The more you bundle, the bigger your savings!

What should I know before booking a Kittery travel package?

So many places to wander around, so many things to experience. With a package, you'll be able to check more of them off your list. Bundle your flights, hotels and rental cars and land big savings.

Can I choose my airline with a Kittery Expedia travel package?

Yes, the choice is yours. Expedia has access to more than 550 partner airlines worldwide, so you can design your Kittery escape according to your travel needs.

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