Ashland Vacations from $608

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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.
Stonybrook Motel & Lodge

Stonybrook Motel & Lodge

2 out of 5
Price was $901, price is now $608 per person
$608
per person
Dec 14 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Manchester (MHT)
7.6/10 Good! (1,001 reviews)

Presidential Mountain Resort

Presidential Mountain Resort

3 out of 5
Price was $1,342, price is now $886 per person
$886
per person
Dec 14 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Manchester (MHT)
9.6/10 Exceptional! (328 reviews)

The Village of Loon Mountain Fixed Rooms

The Village of Loon Mountain Fixed Rooms

2 out of 5
Price was $1,555, price is now $1,038 per person
$1,038
per person
Dec 14 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Manchester (MHT)
8.8/10 Excellent! (71 reviews)
Check-in process was worse . We had late check-in . No one was there at the counter. The phone which was supposed to give the code to get the key was not working. We waited there for more than 3 hours in the cold till 11:30 pm. I would not recommend this place .

Reviewed on Oct 30, 2026

The Village of Loon Mountain

The Village of Loon Mountain

3 out of 5
Price was $1,263, price is now $912 per person
$912
per person
Dec 14 - Dec 21
found 10 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Manchester (MHT)
8.6/10 Excellent! (623 reviews)
We had a wonderful stay! Great location, pools were well maintained and staff was very friendly. Highly recommend!

Reviewed on Oct 30, 2026

InnSeason Resorts Pollard Brook

InnSeason Resorts Pollard Brook

3 out of 5
Price was $1,210, price is now $914 per person
$914
per person
Dec 14 - Dec 21
found 4 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Manchester (MHT)
9.4/10 Exceptional! (969 reviews)
Good points are suite was spacious and it was quiet. But the unit was very outdated. Cabinets and drawers in kitchen weren't clean. Bathrooms so outdated and tubs so slippery, fall risk. Worst part was unit was extremely hot in 20 degree temp. Had to run AC and front desk and facilities just said open a window. Didn't know there was no elevators either.

Reviewed on Oct 30, 2026

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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.
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Ashland Hotel Deals

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
460 North Ashland Road Ashland NH
$130 nightly
The price is $142 total per night from Dec 1 to Dec 2
$142 total
Dec 1 - Dec 2
Total with taxes and fees
Cold Spring Plymouth Resort
Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy Meredith NH
$217 nightly
The price is $236 total per night from Nov 1 to Nov 2
$236 total
Nov 1 - Nov 2
Total with taxes and fees
Mill Falls Resort Collection at the Lake
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $110 total per night from Nov 2 to Nov 3
$110 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
"Great location.. in town for a short visit"

Reviewed on Oct 29, 2026

Best Western Plus Landmark Inn
See all 2,059 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
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 $608 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.