Kittery Holidays

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Top Flight + Hotel Deals in Kittery

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
Price was €1,655, price is now €1,108 per person
€1,108
per person
8 Oct - 12 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Heather was unbelievable in every way. Because of her past excellent service we returned!! She makes this hotel experience a true pleasure. Thank you Heather for your kind and gracious assistance.

Reviewed on 21 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was €2,798, price is now €1,518 per person
€1,518
per person
8 Oct - 12 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) 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 21 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was €2,442, price is now €1,475 per person
€1,475
per person
8 Oct - 12 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) 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 20 Aug 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was €1,680, price is now €1,138 per person
€1,138
per person
8 Oct - 12 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,073 reviews)
Location was amazing. Facilities were clean and staff was friendly. My only complaint is that the pool area was a loud party scene, so much so that I couldn’t spend very long there. Since this was the main reason I chose this hotel over others and paid the $30 plus taxes “resort fee” on top of the regular cost this was disappointing.

Reviewed on 21 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was €2,173, price is now €1,494 per person
€1,494
per person
8 Oct - 12 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (441 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on 16 Aug 2025

Top hotels in Kittery

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 €111 per night from 25 Aug to 26 Aug
€111
25 Aug - 26 Aug
includes taxes & fees
7.6/10 Good! (1,000 reviews)
"Parking very close. Food was light must to have to get there before 8:30 am."

Reviewed on 17 Aug 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 €159 per night from 3 Sept to 4 Sept
€159
3 Sept - 4 Sept
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 16 Aug 2025

Hampton Inn & Suites Kittery-Portsmouth
Ogunquit - The Milestone

Ogunquit - The Milestone

2 out of 5
687 Main Street, Ogunquit, ME
The price is €102 per night from 1 Sept to 2 Sept
€102
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,129 reviews)
"Bed was good but pillows were not very comfortable. Since walls are thin, recommend the property WD40 all of entrance doors and interior doors as the squeak and you can hear them. Overall, we had a nice stay. No issues."

Reviewed on 18 Aug 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.

Frequently asked questions

How much does a Kittery holiday package cost?
You can snap up a holiday package to this destination from €1,108 on Expedia. But how much your holiday to Kittery costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Kittery?
If you're hoping to book a cheap Kittery holiday package, consider travelling in December, January and February. You'll usually find lower rates on flights and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Kittery?
When planning your Kittery holiday, a handful of days will be enough to tour the best spots. Be sure to visit Kittery Historical and Naval Museum — it's one of the main sights in this destination. If you're after more adventure, think about basing yourself here and heading off on some day trips from Kittery.
Is it worth booking a holiday package to Kittery?
Kittery has everything you need for a memorable trip — coastal beaches, walking trails and culture are just the start. Whether you'd like to check out attractions such as Kittery Premium Outlets and Yummies Candy and Nuts, or take the path less traveled, you'll find plenty to explore on your Kittery holiday.
How to find the best Kittery package deals?
Begin your search for a Kittery package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Kittery package deal straight away, simply change 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 holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Kittery holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Kittery?
If you're considering a spur-of-the-moment Kittery holiday, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Kittery?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Kittery.
  2. Budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may come up during your trip to Kittery.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Kittery. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your accommodation and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Kittery holiday package for you.

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