Ashland Vacations from $525

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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 $729, price is now $525 per person
$525
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
7.6/10 Good! (1,003 reviews)
Cozy super old fashioned little motel with a lock and key. Actually loved it here, perfect area and close to everywhere I planned to hike. Definitely would stay here again. Super affordable and the dude at the front desk was super cool

Reviewed on Jun 22, 2026

The Lake Estate on Winnisquam

The Lake Estate on Winnisquam

4.5 out of 5
Save 100% on your flight
Price was $1,856, price is now $1,222 per person
$1,222
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
9.8/10 Exceptional! (35 reviews)
The property was beautiful, exceptionally well-maintained, and spotless throughout. From the lobby to the guest rooms, everything was clean, comfortable, and thoughtfully cared for. The staff was friendly and welcoming, which made our experience even better. It was clear that great attention is given to both the appearance and upkeep of the hotel. We would gladly stay here again and highly recommend it to others looking for a relaxing and enjoyable stay

Reviewed on Jun 24, 2026

Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,004, price is now $728 per person
$728
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
Very nice place clean,friendly

Reviewed on Jun 24, 2026

Eagle Mountain House & Golf Club

Eagle Mountain House & Golf Club

3.5 out of 5
Price was $838, price is now $641 per person
$641
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
The hotel is historical and rooms reflect that. The staff are friendly and very welcoming! The grounds are beautiful and the location is perfect! The bar onsite is fantastic and enjoying a beverage on the porch is magical. Beautiful place!

Reviewed on Jun 21, 2026

The Village of Loon Mountain

The Village of Loon Mountain

3 out of 5
Price was $796, price is now $632 per person
$632
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.6/10 Excellent! (579 reviews)
The place was very nice, very clean, spacious, excellent pools, gym, grill, playground for the kids. Everything great. Just a brown young lady whose host the pool side and gym she should be more polite and sweet with the guest specially with kids. Except it. Everything was great.

Reviewed on Jun 21, 2026

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Stay near popular Ashland attractions

Pauline E Glidden Toy Museum

10.0/5 (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.
See properties

Ashland Hotel Deals

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
460 North Ashland Road Ashland NH
$193 nightly
The price is $209 total per night from Jul 12 to Jul 13
$209 total
Jul 12 - Jul 13
Total with taxes and fees
9.2/10 Wonderful! (224 reviews)
"Great place at a very reasonable rate. Very friendly reception."

Reviewed on Jun 26, 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
$115 nightly
The price is $124 total per night from Jun 29 to Jun 30
$124 total
Jun 29 - Jun 30
Total with taxes and fees
7.8/10 Good! (851 reviews)
"Great for a one night stay. Air conditioning was a little loud. Nice stay. Would stay again"

Reviewed on Jun 19, 2026

Quality Inn Ashland
Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy Meredith NH
$190 nightly
The price is $207 total per night from Jun 30 to Jul 1
$207 total
Jun 30 - Jul 1
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"The property is amazing. You have stores, restaurants right on site. Very convenient. Will definitely be going back!"

Reviewed on Jun 25, 2026

Mill Falls Resort Collection at the Lake
See all 2,110 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 $525 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.