Carlisle Vacation Packages

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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 Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was CA $1,398, price is now CA $921 per person
CA $921
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,011 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $5,163, price is now CA $2,910 per person
CA $2,910
per person
Sep 1 - Sep 8
found 23 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,015 reviews)
Great location and very helpful staff

Reviewed on Jul 16, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $2,653, price is now CA $1,640 per person
CA $1,640
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $4,418, price is now CA $2,801 per person
CA $2,801
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (740 reviews)
There are too many negatives to comment on but here are a few. The fact that this hotel was rated 9.2 on Expedia is an absolute joke. On top of the poor quality, the room was more expensive than any hotel I have ever stayed in whether it was the Four Seasons in Maui or the Mandarin Oriental in London or San Francisco. Some examples: - The hotel is nowhere near the beach or town. Make sure you understand that. - The pool was empty. - The showers near the pool (for cleaning up after the beach) only had cold water. - One of the few nice amenities of the hotel was free bicycles. The seats did not move on them and they had virtually flat tires. - The pipes in other rooms sounded like the roar of an engine. - the grout in the bathrooms had signs of mold. Make no mistake - this is not a high end hotel. It is an Extended Stay with exorbitant prices.

Reviewed on Jul 20, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $2,538, price is now CA $1,727 per person
CA $1,727
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The property was well maintained and close to good restaurants. We had a cooked breakfast every day.

Reviewed on Jul 16, 2026

Ready to book your vacation to Carlisle?

 

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Carlisle Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $280 per night from Jul 26 to Jul 27
CA $280
CA $374 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,591 reviews)
"The room was very clean and the staff real helpful."

Reviewed on Jul 21, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Jul 26 to Jul 27
CA $202
CA $235 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (2,757 reviews)
"Down the hall bathrooms worked way better than expected. Room with bunk was great. Would absolutely stay there again."

Reviewed on Jul 21, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $348 per night from Jul 26 to Jul 27
CA $348
CA $463 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (4,804 reviews)
"It was greatl"

Reviewed on Jul 20, 2026

Omni Boston Hotel at the Seaport
See all 3,479 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

Frequently asked questions

How much does a Carlisle vacation package cost?
You'll find cheap prices from CA $921 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.

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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.