Ashland Vacations from $403

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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.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $656, price is now $403 per person
$403
per person
Feb 26 - Mar 3
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Check in was easy, room was amazing, second time here, looking forward to the next time!

Reviewed on Jan 22, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,512, price is now $972 per person
$972
per person
Mar 10 - Mar 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Amazing stay in Boston. The staff is extremely friendly and helpful, the rooms are updated and clean, the health club was top of the line, and the location is very convenient to a lot of our favorite places in Boston.

Reviewed on Jan 20, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,352, price is now $904 per person
$904
per person
Apr 2 - Apr 6
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) 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

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $918, price is now $617 per person
$617
per person
Mar 29 - Apr 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
I didn’t like that I was surprised with “hospitality fee” for almost $70 upon arrival. Had I known that I would’ve stayed somewhere else. That’s why I paid in advance on Expedia.

Reviewed on Jan 23, 2026

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $981, price is now $667 per person
$667
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,891 reviews)
Clean hotel room and phenomenol staff!

Reviewed on Jan 19, 2026

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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

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
10 Huntington Ave Boston MA
$218 nightly
The price is $254 total per night from Feb 15 to Feb 16
$254 total
Feb 15 - Feb 16
Total with taxes and fees
9/10 Wonderful! (1,439 reviews)
Everything was very good, but something that I'm not agree is that the hotel charge $70 x 3 Parking Fee and we don't have any car for this vacation.

Reviewed on Jan 20, 2026

The Westin Copley Place, Boston, a Marriott Hotel
The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
61 Exeter Street Boston MA
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $204 total per night from Jan 25 to Jan 26
$204 total
Jan 25 - Jan 26
Total with taxes and fees
9.6/10 Exceptional! (1,336 reviews)
Great place and perfect location

Reviewed on Jan 18, 2026

The Lenox Hotel Boston
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 Jan 29 to Jan 30
$125 total
Jan 29 - Jan 30
Total with taxes and fees
9.2/10 Wonderful! (2,238 reviews)
I did not have breakfast but I had some snacks coffee etc while there. Everything was good. Such a great location and fabulous view. Room is perfect for a single person. Staff was friendly rooms were super clean. I will be back!

Reviewed on Jan 21, 2026

citizenM Boston Back Bay
See all 2,016 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 $403 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.