Littleton Vacation Packages
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Your Littleton Vacation
Take the hassle out of organizing your next big adventure with a Littleton vacation package. Whether you're interested in its food, entertainment or other highlights, this city offers limitless opportunities for discovery. Nashoba Valley Ski Area, Kimball Farm and MIT Haystack Observatory are just a few of the many sights worth checking out during your trip to Littleton. Your Littleton vacation is just a few clicks away. Explore flights, accommodations and more on Expedia for a getaway that's tailored just for you.
Top Littleton Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Lighthouse Inn
Price was CA $1,425, price is now CA $1,004 per person
CA $1,004
per person
Jun 11 - Jun 14
just found
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.8/10 Excellent! (182 reviews)
This is a beautiful property located on the beach. It really does not het much better than this. The room was nice and spacious and the views were nothing short of exceptional. The staff was wonderful and a shout out to the GM, John, for being very helpful! And of course the sunsets on West Dennis beach are worth the stay!
Reviewed on Oct 6, 2025
The Langham, Boston
Downtown Boston
Price was CA $3,971, price is now CA $2,181 per person
CA $2,181
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The staff were so kind and let us check in early. They constantly asked how we were enjoying the stay and if there was anything that we needed. The property was clean and super cute!
Reviewed on Apr 13, 2026
Boston Harbor Hotel
North End
Price was CA $2,299, price is now CA $1,416 per person
CA $1,416
per person
May 16 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Classic luxury, a true five-star experience. Spectacular Boston Harbor views, top-notch staff, extra-comfortable bedding, rainfall shower.
Reviewed on Apr 12, 2026
Life House, Nantucket
Nantucket Town
Price was CA $2,531, price is now CA $1,622 per person
CA $1,622
per person
Jun 1 - Jun 6
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (65 reviews)
The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again.
Reviewed on Sep 26, 2025
Littleton Hotel Deals
Four Points by Sheraton Boston Newton
320 Washington Street Newton MA
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Apr 27 to Apr 28
CA $130
CA $146 total
Apr 27 - Apr 28
includes taxes & fees
8.4/10 Very Good! (2,842 reviews)
Room seemed clean. Staff was nice. Breakfast was not complimentary and I did not know that until I already grabbed a plate. I was only told what time breakfast was. Parking was not included, I had to pay which was inconvenient. You get what you pay for here.
Reviewed on Apr 16, 2026
Sheraton Boston Needham Hotel
100 Cabot St Needham MA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Apr 23 to Apr 24
CA $151
CA $168 total
Apr 23 - Apr 24
includes taxes & fees
8.8/10 Excellent! (1,606 reviews)
Good clean hotel with convenient location. Amenities are average. Breakfast option is limited and pretty much same every day. Overall a Good-place to stay for short trips.
Reviewed on Apr 16, 2026
Hilton Boston/Woburn
2 Forbes Rd. Woburn MA
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Apr 24 to Apr 25
CA $179
CA $200 total
Apr 24 - Apr 25
includes taxes & fees
8.6/10 Excellent! (1,280 reviews)
I didn’t know because I didn’t eat anything
Reviewed on Apr 14, 2026
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.
Discover the most popular places to visit in Littleton
Cataldo's Gift & Garden
Take the family on an outing to Cataldo's Gift & Garden during your trip to Littleton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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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.
