Ashland Vacations from $508

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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.
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
Price was $765, price is now $508 per person
$508
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
Room clean. Staff helpful although we were assigned a room at check in only to find someone else in that room! Nice European style breakfast but tea and coffee were not hot. Sufficient easy parking.

Reviewed on Jul 2, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,346, price is now $1,463 per person
$1,463
per person
Aug 21 - Aug 25
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (720 reviews)
The place is really great! The staff by far were the best part, extremely friendly and helpful with everything! We also had a place to store our luggage for when we wanted to go explore but were unable to check-in. The lobby and room were very nice and clean, as well as the amenities like the pool. The shuttle made it very convenient to get around too. Overall wonderful stay and place!

Reviewed on Jul 1, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,208, price is now $1,378 per person
$1,378
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $1,408, price is now $920 per person
$920
per person
Aug 21 - Aug 25
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (193 reviews)
Loved it here! Everyone was friendly and helpful.

Reviewed on Jul 1, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $2,384, price is now $1,572 per person
$1,572
per person
Aug 21 - Aug 25
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (716 reviews)
Chatham Tides is a slice of heaven. Beautiful location. Clean, well maintained. Staff was super helpful with local restaurants. My wife and I gave it a 11/10

Reviewed on Jul 2, 2026

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Stay near popular Ashland attractions

Ashland State Park

7.0/10 (2 reviews)
This 470-acre woodland sanctuary surrounds a reservoir with a 3.5-mile scenic trail and sandy beach. Enjoy summer swimming, fishing, or launch a boat from the ramp for a peaceful day on the water.
See properties

Ashland Hotel Deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $189 total per night from Aug 2 to Aug 3
$189 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (2,403 reviews)
"."

Reviewed on Jul 2, 2026

Hyatt Regency Boston/Cambridge
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $189 total per night from Jul 26 to Jul 27
$189 total
Jul 26 - Jul 27
Total with taxes and fees
8.2/10 Very Good! (548 reviews)
"For the price of the hotel we were expecting more. First there were no elevators for the property so if you are on the second floor you will have a hard time with your luggage, We were on the first floor and we still had to go up two flights of stairs. With a family that was a lot of luggage to take ..."

Reviewed on Jul 2, 2026

The Midtown Hotel MOD Collection by Sonesta
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street Boston MA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $185 total per night from Jul 5 to Jul 6
$185 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (2,822 reviews)
"This hotel was conveniently located but everything else was a bit of a nightmare. You have to ride an elevator to check in, then a different elevator to your room. The room was like a dorm or ship's berth and exactly as wide as the bed is long. The bathroom sink is in the room and you walk between ..."

Reviewed on Jul 2, 2026

citizenM Boston Back Bay
See all 2,106 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 $508 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.