Ashland Vacations from $275
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Your Ashland Vacation
Say farewell to the stress of planning and hello to a Ashland vacation package. With the finer details organized before you go, you can focus on discovering this city, starting with Tenney Mountain, which is great for nature, views and hiking. Make your trip to Ashland even more enjoyable by going sightseeing. Plymouth State University, The Flying Monkey Movie House and Performance Center and Lake Waukewan are some of the big attractions you'll want to explore. No matter your travel plans or budget, organizing a tailored Ashland vacation is a breeze with Expedia.
The Latest Ashland vacation packages
Price found within the past 48 hours. Click for updated prices.
Christmas Farm Inn and Spa
$275
per person
Nov 19 - Nov 22
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Manchester (MHT)
8.8/10 Excellent! (985 reviews)
We had a fantastic time during our stay.If you love Christmas or any other holiday, you will enjoy your time here! Can’t wait to come back. Thank you!
Reviewed on Oct 16, 2026
Stay near popular Ashland attractions
St. Mark's Episcopal Church
10.0/10 (1 review)
St. Mark's Episcopal Church, established in 1855, offers traditional worship in historic Ashland. Visitors can experience organ-accompanied hymns and a welcoming community atmosphere during Sunday morning services.
Ashland Railroad Station Museum
10.0/10 (1 review)
Step back in time at this 1869 railroad station showcasing Ashland's transportation heritage. Explore restored waiting rooms and marvel at the detailed model railroad depicting the station as it appeared in 1893.
Pauline E Glidden Toy Museum
10.0/10 (1 review)
Step back in time at the Glidden Toy Museum, home to over 2,000 antique toys in a historic 1810 plank house. Explore five themed rooms showcasing dollhouses, penny toys, and rare tin treasures from childhood's past.
Whipple House Museum
10.0/10 (1 review)
This 1837 residence showcases Nobel Prize winner George Hoyt Whipple's legacy through period furnishings and family exhibits. Explore twelve preserved rooms including a Victorian bedroom and children's quarters.
Whitten Woods Trailhead
9.4/10 (3 reviews)
Whitten Woods Trailhead: a 500-acre conservation paradise with panoramic lake and mountain views. Explore forest paths to South Peak's expansive vistas or North Peak's woodland experience.
Ashland Hotel Deals
Cold Spring Plymouth Resort
460 North Ashland Road Ashland NH
Fully refundableReserve now, pay when you stay
$129 nightly
$140 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (283 reviews)
"Logement acceptable mais n’étais pas le plus confortable pour le prix et très ancien avec beaucoup de moquettes"
Reviewed on Oct 17, 2026
Mill Falls Resort Collection at the Lake
281 Daniel Webster Hwy Meredith NH
$209 nightly
$226 total
Oct 28 - Oct 29
Total with taxes and fees
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
$101 nightly
$110 total
Nov 1 - Nov 2
Total with taxes and fees
7.8/10 Good! (1,006 reviews)
"Room was clean"
Reviewed on Oct 16, 2026
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 |
Population | 1,250 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Squam Lakes Natural Science Center, Wellington State Park and Museum of the White Mountains |
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Frequently asked questions
How much does an Ashland vacation package cost?
Offering excellent value package deals from $275 on Expedia, you'll be surprised at how little a vacation to Ashland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Ashland?
You can typically find lower prices and better availability in April, November and December. Explore our cheap Ashland vacation packages and you could get some great off-season deals.
How many days is enough for Ashland?
Generally, a handful of days is great for an Ashland vacation. With a well-organized itinerary, you can see all the major sights like Riveredge Marina, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Ashland?
Ashland has all the ingredients you need for a fantastic getaway — walking trails, family-friendly attractions and markets are just the start. Whether you'd like to check out sights like Ashland Railroad Station Museum and Whipple House Museum, or take the path less traveled, there's plenty to see and do on your Ashland vacation.
How to find the best Ashland package deals?
Finding a cheap Ashland package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most economical Ashland package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book an Ashland vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Ashland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Ashland?
If you've got your Ashland travel dates confirmed, book as soon as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Ashland vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Ashland trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
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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.
