Ashland Vacations from $293

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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.

The Latest Ashland vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Springfield West Inn

Best Western Springfield West Inn

2.5 out of 5
Price was $437, price is now $293 per person
$293
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
7.8/10 Good! (1,001 reviews)
My room was comfortable and clean

Reviewed on Aug 21, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $633, price is now $308 per person
$308
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
Price was $882, price is now $569 per person
$569
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (2,072 reviews)
Good value for the price and our family of 5. I would prefer rooms with no carpet. It was fine, but questionable as I smelled chorine. Overall, it was fine. The front desk was helpful and the service was very good.

Reviewed on Aug 21, 2025

Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
Price was $603, price is now $390 per person
$390
per person
Nov 12 - Nov 17
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (474 reviews)
Clean and comfortable. Very easy to park.

Reviewed on Aug 5, 2025

EVEN Hotels Manchester Airport by IHG

EVEN Hotels Manchester Airport by IHG

3.5 out of 5
South End
Save 100% on your flight
Price was $507, price is now $330 per person
$330
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (884 reviews)
This was a good and decent hotel, while being austere. There are few extras but is clean and simple. Felt a bit like a college dorm, but for one night, great!!!

Reviewed on Aug 26, 2025

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Discover the most popular places to visit in Ashland

Ashland State Park

You can take time to visit Ashland State Park during your travels to Ashland. While you're in the area, wander around the parks.

Ashland State Park

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
$179 nightly
The price is $208 total per night from Sep 1 to Sep 2
$208 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (1,665 reviews)
"If you are catching a game at Fenway, this is a perfect spot. Great location."

Reviewed on Aug 23, 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
$169 nightly
The price is $197 total per night from Sep 1 to Sep 2
$197 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (3,808 reviews)
"The staff was very nice and helpful. Great location to many things and a pretty short walk to fenway. Would stay there again."

Reviewed on Aug 25, 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
$228 nightly
The price is $264 total per night from Sep 21 to Sep 22
$264 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (2,109 reviews)
Thanks
"Friendly and helpful staff. We had a great stay. Thank you."

Reviewed on Aug 24, 2025

Hyatt Regency Boston/Cambridge
See all 1,879 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.

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Frequently asked questions

How much does an Ashland vacation package cost?
Offering excellent value package deals from $293 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?
December, January and February are great times to search for cheap Ashland vacation packages. Choosing to travel in less busy periods means you'll typically find better prices on accommodations and flights.
How many days is enough for Ashland?
With a well-planned itinerary, you can easily tick off the top Ashland sights in a handful of days. But if you prefer to discover hidden gems or go on day tours, consider booking your Ashland vacation for longer.
How to find the best Ashland package deals?
Begin your search for an Ashland package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Ashland package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Ashland adventure underway.
Is it cheaper to book an Ashland vacation as a package?
You can enjoy significant savings on your Ashland break by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Ashland?
If you're considering a spontaneous Ashland trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Ashland vacation packages?
Set off on your perfect trip to Ashland with Expedia's Book Now, Pay Later vacations. No need to save up or wait for payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snap up cheap deals before they sell out.

Explore a world of travel with Expedia

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.