Ashland Vacations from $592

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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.
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $697, price is now $592 per person
$592
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Manchester (MHT)
7/10 Good! (1,004 reviews)
Clean room and easy parking

Reviewed on Mar 30, 2026

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Price was $1,051, price is now $831 per person
$831
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Manchester (MHT)
8.8/10 Excellent! (150 reviews)
The rooms were clean but were starting to show signs of age. The bed would squeak and the mattress would sink in the middle. There was a fly in the room, which took forever to get it out. I thought the decor was nice. The concept is of Airbnb rooms but within a hotel. There’s no onsite front desk but there’s daily maintenance it seems. The living room lodge is cozy, the free cocoa/coffee was great, and the game room/pool was nice. Overall, it was a great value and would gladly return.

Reviewed on Mar 26, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,051, price is now $863 per person
$863
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Lebanon (LEB)
9/10 Wonderful! (820 reviews)
Staff were super friendly. Miles was great to deal with. Amazing gentleman and very friendly and helpful. Others were also equally helpful. Loved it!

Reviewed on Apr 9, 2026

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
Price was $1,073, price is now $906 per person
$906
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Manchester (MHT)
9.4/10 Exceptional! (451 reviews)
Great place. Clean, warm. Very comfortable beds. Nice restaurants in town

Reviewed on Apr 8, 2026

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $1,253, price is now $1,063 per person
$1,063
per person
May 28 - May 31
found 10 hours ago
Roundtrip flight included
Houston (IAH) to Manchester (MHT)
9.6/10 Exceptional! (362 reviews)
Everything was above and beyond. Our room was lovely. Every staff member was great! I would highly recommend the BVI.

Reviewed on Jan 29, 2026

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Discover the most popular places to visit in Ashland

Pauline E Glidden Toy Museum

You can spend time studying the exhibits at Pauline E Glidden Toy Museum in Ashland. Stroll along the lakeside or discover the area's mountain views.

Pauline E Glidden Toy Museum

Ashland Railroad Station Museum

You can spend time browsing the exhibits at Ashland Railroad Station Museum in Ashland. Wander the lakeside or discover the area's mountain views.

Ashland Railroad Station Museum

Whipple House Museum

You can spend time exploring the galleries in Whipple House Museum during your trip to Ashland. Stroll along the lakeside or discover the area's mountain views.

Whipple House Museum

Ashland Hotel Deals

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
460 North Ashland Road Ashland NH
$147 nightly
The price is $160 total per night from Apr 24 to Apr 25
$160 total
Apr 24 - Apr 25
Total with taxes and fees
9.2/10 Wonderful! (204 reviews)
Very clean property, great price! Unit was great, plenty of space, well equipped. Great location, easy drive to multiple ski resorts.

Reviewed on Mar 30, 2026

Cold Spring Plymouth Resort
Quality Inn Ashland

Quality Inn Ashland

2.5 out of 5
53 West St Ashland NH
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $97 total per night from Apr 11 to Apr 12
$97 total
Apr 11 - Apr 12
Total with taxes and fees
7.8/10 Good! (838 reviews)
The room was clean, comfortable, and well-maintained. The bed was especially cozy, and I appreciated the quiet atmosphere at night. Housekeeping did a great job keeping everything fresh during my stay.

Reviewed on Apr 7, 2026

Quality Inn Ashland
Steele Hill Resorts

Steele Hill Resorts

3 out of 5
516 Steele Hill Road Sanbornton NH
$189 nightly
The price is $205 total per night from Apr 12 to Apr 13
$205 total
Apr 12 - Apr 13
Total with taxes and fees
8.4/10 Very Good! (802 reviews)
The easter buffet was over priced, my daughter just turned 12 and was charged as an adult..we literally had a couple pieces of bacon/sausage and a waffle…my son had a couple pieces of bacon and some fruit and it cost us $111, it was disappointing but the rest of the stay was amazing!

Reviewed on Apr 7, 2026

Steele Hill Resorts
See all 2,051 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 $592 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.