Ashland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Swetha Srinivasan
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug. 2 - Aug. 4
found 3 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Always a great stay. Property is getting a little bit dated and could use a refresh. The house keeping staff is the best!

Reviewed on Jun. 3, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 31 - Sep. 3
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.4/10 Exceptional! (274 reviews)
This is a beautiful hotel with a great gym and first class service. The housekeeping team is world class.

Reviewed on Jun. 5, 2024

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Aug. 1 - Aug. 4
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (155 reviews)
From the moment we walked into the lobby at Beacon Hill Hotel we were greeted and treated like VIPs. The room, was a corner, looking out over Charles Street. Perfectly comfortable and artfully appointed. My only complaint and this is silly the pillows too puffy. We dined there as well and the food and service was superb.

Reviewed on May 23, 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug. 31 - Sep. 3
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
EVERYTHING WAS OUTSTANDING

Reviewed on Jun. 4, 2024

La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
Assembly Square
Save 100% on your flight
per person
Aug. 20 - Aug. 27
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (1,944 reviews)
Great time great room great service alot of construction around the property so road os pretty bad to get into the parking lot

Reviewed on Jun. 4, 2024

Ashland Hotel Deals

Four Points by Sheraton Boston Newton
Four Points by Sheraton Boston Newton
3.5 out of 5
320 Washington Street, Newton, MA
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Jul. 2 to Jul. 3
CA $141
CA $158 total
includes taxes & fees
Jul 2 - Jul 3
8/10 Very Good! (2,072 reviews)
"Hotels was nice. Check in was seamless. Property was nice. Highway sound was a bit much."

Reviewed on Jun. 5, 2024

Four Points by Sheraton Boston Newton
Copley Square Hotel
Copley Square Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Jul. 2 to Jul. 3
CA $239
CA $278 total
includes taxes & fees
Jul 2 - Jul 3
8.4/10 Very Good! (2,346 reviews)
"Free coffee and water is always a nice perk!"

Reviewed on Jun. 3, 2024

Copley Square Hotel
The Arcadian powered by Sonder
The Arcadian powered by Sonder
3.5 out of 5
1200 Beacon St, Brookline, MA
The price is CA $187 per night from Jul. 2 to Jul. 3
CA $187
CA $209 total
includes taxes & fees
Jul 2 - Jul 3
7.8/10 Good! (2,227 reviews)
"It was a very nice, clean and quite place. If we come back to Boston we would stay there again."

Reviewed on Jun. 5, 2024

The Arcadian powered by Sonder
See all 1,726 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?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Ashland from just CA $1,011. And the more you bundle, the more cash you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to Ashland?
Crafting your own Ashland vacation package with Expedia is one of the easiest ways to save. We have access to more than 550 airlines and 1,000,000 hotels all over the world. With such a huge range to pick from, you’ll have no trouble pulling together your next dream adventure.
Where should I stay in Ashland?
A getaway to Ashland isn’t complete without seeing Framingham State University, Metrowest Medical Center - Framingham Campus and Ashland State Park. Stay near these tourist attractions and make sightseeing simple.
What are the top hotels in Ashland?
Whether you’re planning to stay for one or several nights in Ashland, you’ll get a great night’s rest at Warren Conference Center and Inn. This place is a favorite with plenty of travelers.
How far in advance should I book my Ashland vacation?
While prices fluctuate, we generally suggest booking your seats as soon as possible. Most international fares can be found on Expedia up to 12 months in advance. If circumstances have left you booking late, you might still be in luck. Cheap tickets to Ashland sometimes appear only weeks before departure.
What does an Expedia Ashland travel package include?
With Expedia, you can choose a combination of hotels, car rentals and flights to create your perfect Ashland travel package. Once you’ve made your booking, you can add on all the fun stuff like tours and activities. Remember — the more you bundle, the more discounts you’ll get!
What should I know before booking an Ashland travel package?
Bundling your bookings into an Ashland vacation package is the easiest way to organize your trip. Not only that, you’ll get great discounts when you combine your hotels, flights and car rentals. Once you’ve booked, why not add on an activity or a tour?
Can I choose my airline with an Ashland Expedia vacation package?
You sure can. We offer more than 550 airline partners all over the world, so pick the carrier that matches your budget and travel needs.
If I'm not able to travel, can I cancel my Ashland vacation package?
Don’t worry if you’re rethinking your Ashland vacation package — you can cancel or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We get that life can occasionally throw a spanner in the travel works, so look up our Customer Service Portal if that happens. When you’re ready to make changes, we’ll be here to help.

Discover the most popular places to visit in Ashland

Image for Ashland State Park

Ashland State Park

Explore the great outdoors at Ashland State Park, a lovely green space in Ashland. Stroll along the lakeside or visit the shops while you're in the area.

Ashland State Park

Other vacations you might like

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