Ashland Vacations from $428

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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.
Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Price was $597, price is now $428 per person
$428
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
9.2/10 Wonderful! (284 reviews)
Great place to stay in the plymouth Ashland area!!

Reviewed on Nov 10, 2026

Stonybrook Motel & Lodge

Stonybrook Motel & Lodge

2 out of 5
Price was $847, price is now $542 per person
$542
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Manchester (MHT)
7.6/10 Good! (1,001 reviews)
No pool! And a run down property. I did not get the deluxe double room that I booked on Hotels.com (Expedia on their end). He said this is the 3rd time it has happened. I told him to call and fix it. He knows. He at first gave me a queen room when my booking was 2 beds. Then switched to a 2 bed room but so bad! The toilet overflowed from the tank and he came and did not fix it. Did again the next day. He should have given me the nice room that i n

Reviewed on Nov 11, 2026

Christmas Farm Inn and Spa

Christmas Farm Inn and Spa

3 out of 5
Price was $1,673, price is now $1,213 per person
$1,213
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
8.8/10 Excellent! (1,010 reviews)
Charming place. Highly recommend it.

Reviewed on Nov 14, 2026

The Inn at Thorn Hill & Spa

The Inn at Thorn Hill & Spa

4 out of 5
Price was $2,264, price is now $1,654 per person
$1,654
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
9.8/10 Exceptional! (1,002 reviews)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
Price was $884, price is now $657 per person
$657
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Manchester (MHT)
9.2/10 Wonderful! (480 reviews)
5

Reviewed on Nov 12, 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.
See properties

Ashland Hotel Deals

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
460 North Ashland Road Ashland NH
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $143 total per night from Nov 30 to Dec 1
$143 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (300 reviews)
"Great place to stay in the plymouth Ashland area!!"

Reviewed on Nov 10, 2026

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 15 to Nov 16
$236 total
Nov 15 - Nov 16
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 17 to Nov 18
$110 total
Nov 17 - Nov 18
Total with taxes and fees
Best Western Plus Landmark Inn
See all 2,036 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 $428 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.