Ashland Vacations from $270

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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.
Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
Price was $394, price is now $270 per person
$270
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
9/10 Wonderful! (494 reviews)
Ready! And very clean!

Reviewed on Nov 28, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $953, price is now $442 per person
$442
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2 out of 5
Beacon Hill
Save 100% on your flight
Price was $676, price is now $411 per person
$411
per person
Jan 31 - Feb 7
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
7.6/10 Good! (102 reviews)
Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌

Reviewed on Oct 27, 2025

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

2 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $570, price is now $380 per person
$380
per person
Jan 31 - Feb 7
found 5 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.4/10 Very Good! (268 reviews)
The kitchen isn't fully equipped for cooking. I found some culinary utensils incl. a pan and a pot. But there wasn't any stove to cook. The shops nearby are great incl. Trader Joe's and Maruichi.

Reviewed on Nov 4, 2025

Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

4 out of 5
East Boston
Save 100% on your flight
Price was $781, price is now $535 per person
$535
per person
Jan 31 - Feb 7
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.2/10 Wonderful! (1,732 reviews)
It was a bit noisy as the wind was whipping, but view was beautiful with ocean and city lights. Staff was really great!! Helped us with parking etc...

Reviewed on Dec 6, 2025

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Discover the most popular places to visit in Ashland

Ashland State Park

3.5/5(2 reviews)

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

Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $195 total per night from Dec 21 to Dec 22
$195 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,241 reviews)
Staff was fantastic

Reviewed on Dec 8, 2025

Hilton Boston Back Bay
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street Boston MA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from Dec 21 to Dec 22
$125 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (2,113 reviews)
Very small but clean room, don't like the self check in either.

Reviewed on Dec 11, 2025

citizenM Boston Back Bay
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
1200 Beacon St Brookline MA
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $149 total per night from Dec 16 to Dec 17
$149 total
Dec 16 - Dec 17
Total with taxes and fees
8/10 Very Good! (3,815 reviews)
Great location

Reviewed on Dec 8, 2025

The Arcadian Hotel
See all 1,983 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.

Find the Best Ashland Vacation Packages

Ashland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
15,800
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Apex Entertainment Center, Hopkinton State Park and Fun and Games Family Entertainment Center

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Frequently asked questions

How much does an Ashland vacation package cost?
Offering excellent value package deals from $270 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.

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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.