Ashland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Your Ashland Vacation

Take the stress out of planning your next amazing adventure with a Ashland vacation package. Whether you're interested in its history, food or something else, this city offers countless exciting experiences to delve into. If your trip to Ashland includes a little sightseeing, visit popular attractions like Framingham State University, Shoppers World and Natick Collection. That dream Ashland vacation is a couple of clicks away. Search hotels, airfares and more on Expedia for a trip that's tailored to suit your style.

Top Ashland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Excellent hotel with friendly staff, clean and comfortable rooms with a Starbucks! We love the cookies at check in. always a winner. It is in a weird location but for our one night it was great.

Reviewed on Jul. 14, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 4
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

Ready to book your vacation to Ashland?

 

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Ashland Hotel Deals

citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Jul 20 to Jul 21
CA $252
CA $293 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,408 reviews)
"Always a great stay"

Reviewed on Jul. 11, 2025

citizenM Boston Back Bay
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Jul 20 to Jul 21
CA $187
CA $218 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (3,739 reviews)
"The location is great. Everything is walking distance."

Reviewed on Jul. 13, 2025

Copley Square Hotel, a FOUND Hotel
Hyatt Regency Boston/Cambridge
Hyatt Regency Boston/Cambridge
4 out of 5
575 Memorial Drive, Cambridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Aug 10 to Aug 11
CA $197
CA $260 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,976 reviews)
"Fantastic location for 4th of July weekend as fireworks were set off on the nearby Charles."

Reviewed on Jul. 10, 2025

Hyatt Regency Boston/Cambridge
See all 1,860 properties in Ashland
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Ashland vacation package cost?
Offering excellent value package deals from CA $631 on Expedia, you'll be surprised at how little a vacation to Ashland costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Ashland?
The off-season is the best time to travel to Ashland if you're trying to save. Another tip for finding cheap Ashland vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Ashland?
Typically, a handful of days is great for an Ashland vacation. With a carefully crafted itinerary, you can go to all the best sights such as Shoppers World, as well as discover some hidden treasures along the way.
How to find the best Ashland package deals?
Use Expedia's handy filters to help you find some of the best Ashland 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 break for midweek, or browse for Ashland package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book an Ashland vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Ashland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Ashland?
If you're considering an impromptu Ashland adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Ashland?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred time of year and the available activities will also help you decide when to visit Ashland.
  2. Plan your budget wisely: As well as the price of your stay, you should consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Ashland.
  3. Determine how many days away: Start by listing all the activities and sights you want to experience in Ashland. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick an Ashland vacation package that brings all your bookings together.

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