Carlisle Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Boston Lodge and Suites

Boston Lodge and Suites

Dorchester
CA $701
per person
Nov 8 - Nov 11
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
The apt was tidy. Enough to sleep 8. Bathrooms were clean and updated. Parking can be difficult to find. It's about an hour from Salem.

Reviewed on Oct 4, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
CA $1,059
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
The Newbury Boston

The Newbury Boston

Back Bay
Save 100% on your flight
CA $1,340
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (734 reviews)
The Langham, Boston

The Langham, Boston

Downtown Boston
Save 100% on your flight
CA $1,469
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The Langham is refined and just brilliant in guest services. Always looking to book with them where ever we travel, its just an assured luxurious and comfortable stay.

Reviewed on Oct 7, 2026

The Monty Boston

The Monty Boston

Downtown Boston
Save 100% on your flight
CA $2,706
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (41 reviews)
The condo was great, it was nice size for a group of 6 of us. The host was Peter was very easy to communicate with. The location for us was great, we could walk to alot of places.

Reviewed on Oct 4, 2026

Ready to book your vacation to Carlisle?

Choose your dates

Carlisle Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $375
CA $495 total
Nov 1 - Nov 2
includes taxes & fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $204
CA $237 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (2,947 reviews)
"Had a great 4-night stay at the Revolution! We reserved a room with an en suite bathroom. The room was small, but mighty! Innovative layout made the room workable for 2 people with carry on luggage. Good shower pressure and a super comfy King bed! We were always greeted by helpful staff in the lobby. ..."

Reviewed on Oct 7, 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $269
CA $361 total
Nov 1 - Nov 2
includes taxes & fees
9.6/10 Exceptional! (5,084 reviews)
"Lovely comfortable hotel. Staff were lovely."

Reviewed on Oct 7, 2026

Seaport Hotel Boston
See all 3,356 properties in Carlisle
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.
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Stay near popular Carlisle attractions

Great Brook Farm State Park

6.0/10 (1 review)
You can take time to visit Great Brook Farm State Park during your travels to Carlisle. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Malcolm Preserve

Explore the great outdoors at Malcolm Preserve, a lovely green space in Carlisle. Attend a sporting event while in this family-friendly area or simply enjoy the top-notch restaurants.
See properties

Frequently asked questions

How much does a Carlisle vacation package cost?
You'll find cheap prices from CA $701 on Expedia for your Carlisle getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Carlisle costs.
What are the cheapest months to go to Carlisle?
The off-season is the best time to travel to Carlisle if you're trying to save. Another tip for scoring cheap Carlisle vacation packages? Try to avoid public holidays and any major festivals.
How many days is enough for Carlisle?
You can easily explore all the leading sights in Carlisle within a few days, including the must-see Nashoba Valley Ski Area. If you're looking for an extended Carlisle vacation, look at what kind of excursions and activities are available in the area.
Is it worth booking a vacation package to Carlisle?
Carlisle offers everything you need for a wonderful escape. Get your Carlisle vacation off to a flying start by visiting top attractions like Great Brook Farm State Park.
How to find the best Carlisle package deals?
Use Expedia's filters to help you find some great Carlisle package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Carlisle package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Carlisle vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging stays and flights individually. Better still, you can personalize your Carlisle escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Carlisle?
If you're considering an impromptu Carlisle getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Carlisle?
  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Carlisle.
  2. Set your budget: Consider costs such as flights, transportation and food when working out how much to set aside for your trip to Carlisle. Then, pick a property that matches your budget, whether that's an economical option or a lavish getaway.
  3. Decide how long to go away for: Now that you know more about Carlisle, you can figure out the ideal length of your vacation. Put together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Carlisle vacation package.

Explore a world of travel with Expedia

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