Kittery Vacations

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Kittery Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Iris Hotel Boston

Iris Hotel Boston

Coolidge Corner
$1,261
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Book a stay at this business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.
The stay at the Iris Hotel Boston was perfect! The staff went above and beyond to accommodate, make comfortable, welcome us. The bartender was outstanding! The room was beautiful with every need anticipated. Convenient and fun neighborhood with many restaurant, cuisine, shopping and transportation options. I will certainly be back!

Reviewed on Aug 11, 2026

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

North Brookline
Save 100% on your flight
$1,742
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Stay at this apartment in Brookline. Enjoy free WiFi, parking (surcharge), and air conditioning. Popular attractions Fenway Park and Harvard Square are located nearby.
This is more like university housing than anything else. The building is full of students and poorly maintained, with visitors following others into the entrance. Carpeting is stained, paint is chipping, blinds are broken, the a/c didn't work, the hallway smells. Communication with the Evonify owners was poor, and we had to go through Hotels.com to receive our access code/registration in time for our arrival and, ultimately, a refund. We left a few minutes after we entered the unit. Not recommended. It is not the sunny, pristine, and secure apartment that appears in the photos.

Reviewed on Jul 6, 2026

The Concord Hotel

The Concord Hotel

South End
Save 100% on your flight
$1,445
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Stay at this aparthotel in Boston. Enjoy free WiFi and air conditioning. Popular attractions Copley Square and Fenway Park are located nearby.
The building is not new. Hallway was musty. Boxes in the entry way. People sitting on the front stoop smoking, Dirty wash cloth on the stair railing. Management company only communicated via text and wasn't very friendly at all. I would not stay there again.

Reviewed on Aug 9, 2026

The Atlas Hotel

The Atlas Hotel

Allston
Save 100% on your flight
$1,641
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park are located nearby.
The hotel was clean and well maintained. Very innovative designed. The staff was constantly hospitable - opening every door when we enter. The only downside was the room next to us was very loud on our last night which kept us up most of the night - nothing to do with the hotel. I didn’t complain and am hoping for some compensation back.

Reviewed on Aug 10, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

Save 100% on your flight
$2,157
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Burlington Mall and Minute Man National Historical Park are located nearby.
This Inn is a beautiful old building with a long history. It is located within easy walking distance of downtown Lexington with all its history. The Inn had wonderful rooms, a great staff and a top rate restaurant all in one place. Highly recommend!

Reviewed on Jul 13, 2026

The Charles Hotel

The Charles Hotel

West Cambridge
Save 100% on your flight
$2,610
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
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Kittery Vacation Packages

Looking to save money and time on your next holiday to Kittery? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Kittery the best one yet. With just a few clicks, you can pick the best Kittery vacation package for you. We have an incredible selection of accommodations and flight, and Kittery endeavors to choose from.

Kittery Hotel Deals

Our listings include lodgings that are close to all the Kittery points of interest, and others that are just outside the city center for a more restful retreat.

We have great deals on everything from luxury hotels that meet all the vacation must-haves to affordable accommodations perfect for those on looking to save. You can search our vast catalog of possibilities and pick the accommodation that is ideal for you and your family. With AARP Travel Center's Kittery hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Kittery

Kittery is the ideal town when you wish to a break from it all. With only around 9,653 people in the city, this quaint town is just right for a quite vacation. If you want to take walk through the past, then you are in luck as Kittery has a noteworthy historic district.

The AARP Travel Center "Things to Do" page has more great activities that you can book.

Save with a Kittery Vacation Package

As an AARP Member, you can take advantage of all the great savings. You can save on select hotels worldwide, flights, and also rental cars. No matter what Kittery vacation bundle you select, your membership savings helps you get a great deal. So what are you waiting for? Bundle today and get ready for your Kittery vacation.

Top Hotel Deals

Home2 Suites By Hilton Kittery

Home2 Suites By Hilton Kittery

139 Old Post Road Kittery ME
1.5 km from city center
Book a stay at this business-friendly hotel in Kittery. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Kittery Premium Outlets and Market ...
Coachman Inn

Coachman Inn

380 US Route 1 Kittery ME
3.41 km from city center
Book a stay at this business-friendly hotel in Kittery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn & Suites Kittery-Portsmouth

Hampton Inn & Suites Kittery-Portsmouth

275 US Route 1 Kittery ME
2.45 km from city center
Book a stay at this business-friendly hotel in Kittery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Ashworth by the Sea

Ashworth by the Sea

295 Ocean Blvd Hampton NH
20.31 km from city center
Book a stay at this beach hotel in Hampton. Enjoy 3 restaurants, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms ...
Ocean Sands at York Beach

Ocean Sands at York Beach

277 Long Beach Avenue York Beach ME
11.98 km from city center
Book a stay at this beach motel in York Beach. Enjoy an outdoor pool, parking (surcharge), and a garden. Our guests praise the pool and the helpful staff in ...
Ocean Surf at York Beach

Ocean Surf at York Beach

780 York Street (Rte 1A) York Beach ME
11.36 km from city center
Book a stay at this beach motel in York Beach. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the pool and the helpful staff ...
Ogunquit - The Milestone

Ogunquit - The Milestone

687 Main Street Ogunquit ME
22.76 km from city center
Book a stay at this business-friendly motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in ...
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

17 Post Road Ogunquit ME
23.34 km from city center
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Anchorage Inn and Resort

Anchorage Inn and Resort

265 Long Beach Avenue York Beach ME
12.12 km from city center
Book a stay at this beach hotel in York Beach. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Ogunquit Tides Resort

Ogunquit Tides Resort

548 Main Street (U.S. Route 1) Ogunquit ME
22.11 km from city center
Book a stay at this beach motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. ...
Lamie's Inn and The Old Salt Restaurant

Lamie's Inn and The Old Salt Restaurant

490 Lafayette Rd Hampton NH
18.13 km from city center
Book a stay at this business-friendly inn in Hampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the restaurant and the helpful staff ...
Wells-Ogunquit Resort Motel & Cottages

Wells-Ogunquit Resort Motel & Cottages

203 Post Road Wells ME
23.96 km from city center
Book a stay at this business-friendly hotel in Wells. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
The Sea View Motel

The Sea View Motel

417 Main Street Ogunquit ME
21.66 km from city center
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Stage Run By The Sea

Stage Run By The Sea

2 Kingfield Avenue at U.S Route One Ogunquit ME
21.86 km from city center
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ogunquit ...
The Beach House Inn

The Beach House Inn

211 Beach Avenue Kennebunk ME
34.67 km from city center
Book a stay at this beach hotel in Kennebunk. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms ...
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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.