Carlisle Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
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Your Carlisle Vacation
Reserve a Carlisle vacation package and prepare to experience the best of this lively city. Consider basing yourself in the neighborhood of Ballardvale, which is good for watersports, nature and history. Fill your schedule with tours of Nashoba Valley Ski Area, Louisa May Alcotts Orchard House and Clara Sexton House, some of the top attractions you simply have to see during a trip to Carlisle. No matter your travel plans or budget, organizing a tailored Carlisle vacation is a piece of cake with Expedia.
Top Carlisle Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was CA $2,024, price is now CA $1,255 per person
CA $1,255
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
The Langham, Boston
Downtown Boston
Price was CA $3,051, price is now CA $1,650 per person
CA $1,650
per person
Jun 27 - Jun 30
found 17 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
Eurostars The Boxer
West End
Price was CA $2,765, price is now CA $1,798 per person
CA $1,798
per person
Jun 18 - Jun 22
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,435 reviews)
Clean room and good staff. Room is a bit outdated
Reviewed on Apr 15, 2026
The Ritz-Carlton, Boston
Downtown Boston
Price was CA $4,894, price is now CA $3,218 per person
CA $3,218
per person
Jun 27 - Jun 30
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (449 reviews)
Club level is well worth it. The service was wonderful
Reviewed on Apr 16, 2026
Carlisle Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from May 10 to May 11
CA $232
CA $316 total
May 10 - May 11
includes taxes & fees
9.6/10 Exceptional! (4,194 reviews)
A
Reviewed on Apr 18, 2026
Hilton Boston Park Plaza
50 Park Plaza Boston MA
The price is CA $258 per night from May 10 to May 11
CA $258
CA $356 total
May 10 - May 11
includes taxes & fees
8.4/10 Very Good! (3,120 reviews)
The rooms were clean. The hotel was quiet especially considering it is Patriot's Day weekend and very busy. All staff was very nice, friendly, and helpful.
Reviewed on Apr 18, 2026
Harborside Inn Of Boston
185 State St Boston MA
The price is CA $282 per night from Apr 26 to Apr 27
CA $282
CA $329 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (6,459 reviews)
Very clean, perfect stay not too expensive
Reviewed on Apr 18, 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.
Explore a world of travel with Expedia
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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.
