Ashland Vacations from $591

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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.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $963, price is now $591 per person
$591
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 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 $1,945, price is now $1,160 per person
$1,160
per person
Aug 20 - Aug 27
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $3,472, price is now $2,138 per person
$2,138
per person
Aug 20 - Aug 27
found 21 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (722 reviews)
great

Reviewed on Jul 9, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $5,326, price is now $3,311 per person
$3,311
per person
Aug 12 - Aug 17
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,554, price is now $968 per person
$968
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)

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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
$156 nightly
The price is $181 total per night from Aug 9 to Aug 10
$181 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (2,434 reviews)
"The restaurant was exceptional"

Reviewed on Jul 9, 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! (587 reviews)
"Limited breakfast, just coffee and a bun. Very small bathroom. No microwave ovens at all, not in the room or in the lobby. Expensive parking 45/night."

Reviewed on Jul 9, 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
$179 nightly
The price is $208 total per night from Jul 19 to Jul 20
$208 total
Jul 19 - Jul 20
Total with taxes and fees
9.4/10 Exceptional! (2,851 reviews)
"Clean rooms, love the air conditioning and how cozy it is"

Reviewed on Jul 9, 2026

citizenM Boston Back Bay
See all 2,110 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 $591 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.