Ashland Vacations from $400
Book a Hotel + Flight or Car together to unlock savings
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.
The Village of Loon Mountain
$400
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Manchester (MHT)
8.6/10 Excellent! (594 reviews)
The whole room was clean.
The whole experience was excellent. That's why we've been going there for so many years ! We started to go to Loon Mountain Resort since 2003. My son was 6 months old. He will be 23 years old in December. We started with a room above the check-in office. We have been there, until 2016 in late August. We have been in the condos on the left side many times. We haven't been there because we were going every year since to Europe and Asia as well. We love the experience, that's why we returned !!!
Excellent
Reviewed on Aug 21, 2026
Wildcat Inn & Tavern
$607
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)
9/10 Wonderful! (331 reviews)
We had a great experience at this historic Inn. Our room was meticulously clean, and comfortable with good amenities. Check in was seemless and staff were friendly and helpful.
Reviewed on Aug 21, 2026
Extended Stay America Suites - Nashua - Merrimack
$872
per person
Oct 12 - Oct 16
found 10 hours ago
Roundtrip non-stop flight included
New York (JFK) to Manchester (MHT)
7.2/10 Good! (955 reviews)
Spacious room, smart design for longer term rental. Chairs and couches were torn up, vinyl faux leather shedding.
Reviewed on Aug 17, 2026
Stay near popular Ashland attractions
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.
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.
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.
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.
Ashland Hotel Deals
Cold Spring Plymouth Resort
460 North Ashland Road Ashland NH
Fully refundableReserve now, pay when you stay
$147 nightly
$160 total
Sep 7 - Sep 8
Total with taxes and fees
9.2/10 Wonderful! (251 reviews)
"We were pleased with our accomodation as it was like being in a small vacation home. The kitchen was equipped for meal prep although we ate out all our meals. TV had plenty of channels and there was a small private rear deck. We might have used the pool but we had to drive to it from our property. ..."
Reviewed on Aug 22, 2026
Waterfront Ashland Home ~ 2 Mi to Downtown!
Ashland NH
9/10 Wonderful! (12 reviews)
"Gorgeous home. Location was perfect for our family with big and little kids. Shallow water for little to play dock w diving board for bigger kids. Stocked kitchen comfy beds. Owner stays close by to answer questions. Would stay again 100%. Pet friendly, was able to bring dog last minute he was very ..."
Reviewed on Jul 20, 2026
Mill Falls Resort Collection at the Lake
281 Daniel Webster Hwy Meredith NH
$192 nightly
$208 total
Aug 31 - Sep 1
Total with taxes and fees
8.4/10 Very Good! (1,015 reviews)
"Everything was smooth and great ! Thank you!"
Reviewed on Aug 21, 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 $400 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.