Ashland town center aerial view panorama including Federated Church and Town Hall in Ashland, Massachusetts MA, USA.

Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

Charming Century House - Next Door to Ashland University

Charming Century House - Next Door to Ashland University
Ashland
10.0 out of 10, Exceptional, (119 reviews)
"Another great stay "
United States
Ryan O.
$145 nightly
The price is $145
Jun 23 - Jun 24
Total with taxes and fees
Charming Century House - Next Door to Ashland University

Relax, Unwind & Take in the Gorgeous Scenery at Pinehill Hideaway!

Relax, Unwind & Take in the Gorgeous Scenery at Pinehill Hideaway!
Ashland
10.0 out of 10, Exceptional, (40 reviews)
"The entire property was gorgeous and the host made the entire stay so welcoming."
United States
Krystian G.
Relax, Unwind & Take in the Gorgeous Scenery at Pinehill Hideaway!

2-Story Cozy Pinehill Hideaway in Ashland/Mifflin with AC & Hot Tub!

2-Story Cozy Pinehill Hideaway in Ashland/Mifflin with AC & Hot Tub!
Ashland
10.0 out of 10, Exceptional, (4 reviews)
"This is a beautiful wooded retreat, perfect for families, and anyone wanting a base to enjoy the many different activities in the area. Would absolutely stay here again!"
United States
Ted B.
2-Story Cozy Pinehill Hideaway in Ashland/Mifflin with AC & Hot Tub!

Willard Home On Working Farm w/ Water Views!

Willard Home On Working Farm w/ Water Views!
3.0 star property
Willard
$305 nightly
The price is $305
Jul 5 - Jul 6
Total with taxes and fees
Willard Home On Working Farm w/ Water Views!

Willard Home On Working Farm w/ Water Views!

Willard Home On Working Farm w/ Water Views!
Willard
10.0 out of 10, Exceptional, (1 review)
"Beautifully remodeled home on a nice little farm property with a pond. Everything was new and fresh. Host was responsive to requests during stay. Would stay here again!"
United States
Kurt B.
$311 nightly
The price is $311
Jul 5 - Jul 6
Total with taxes and fees
Willard Home On Working Farm w/ Water Views!

Unplug at cabin for 2

Unplug at cabin for 2
Polk
9.8 out of 10, Exceptional, (82 reviews)
" My wife and I went there for our 14th anniversary and had the best time. We don't get away much, but this was just what we needed."
United States
Daniel F.
$105 nightly
The price is $105
Jun 21 - Jun 22
Total with taxes and fees
Unplug at cabin for 2

Tiny Cabin on the outskirts of Mohican State Park

Tiny Cabin on the outskirts of Mohican State Park
Perrysville
10.0 out of 10, Exceptional, (119 reviews)
"cozy little cabin great access to mohican trails "
United States
noah b.
$226 nightly
The price is $235
Jun 21 - Jun 22
Total with taxes and fees
Tiny Cabin on the outskirts of Mohican State Park

Just minutes from Mansfield Speedway MidOhio Sportscar Ohio State Reformatory

Just minutes from Mansfield Speedway MidOhio Sportscar Ohio State Reformatory
Mansfield
10.0 out of 10, Exceptional, (60 reviews)
"Everything was wonderful! Love how well stocked everything is - coffee bar, toiletries - I never have to worry if I've forgotten something."
United States
April B.
$169 nightly
The price is $169
Jun 22 - Jun 23
Total with taxes and fees
Just minutes from Mansfield Speedway MidOhio Sportscar Ohio State Reformatory

Lake Fork Schoolhouse Mohican and Amish Country Romantic Getaway

Lake Fork Schoolhouse Mohican and Amish Country Romantic Getaway
Jeromesville
9.8 out of 10, Exceptional, (16 reviews)
"We appreciate the history of the school house and how the owner celebrated its heritage. Will definitely be back. "
United States
Sasha
$305 nightly
The price is $308
Jun 24 - Jun 25
Total with taxes and fees
Lake Fork Schoolhouse Mohican and Amish Country Romantic Getaway

Brand new studio apartment with queen bed, queen pull out, WIFI and AC .

Brand new studio apartment with queen bed, queen pull out, WIFI and AC .
Wooster
10.0 out of 10, Exceptional, (7 reviews)
"Very cozy and quite, relaxing place to unwind"
United States
michael h.
$134 nightly
The price is $140
Jun 21 - Jun 22
Total with taxes and fees
Brand new studio apartment with queen bed, queen pull out, WIFI and AC .

Cozy, cute home close to College of Wooster and Amish Country, Ohio

Cozy, cute home close to College of Wooster and Amish Country, Ohio
Wooster
9.8 out of 10, Exceptional, (24 reviews)
"We had a great stay and would recommend "
United States
Johnson D.
$285 nightly
The price is $303
Jun 21 - Jun 22
Total with taxes and fees
Cozy, cute home close to College of Wooster and Amish Country, Ohio

The Diamond House

The Diamond House
Mansfield
9.8 out of 10, Exceptional, (59 reviews)
"Very clean and updated house! Was in the perfect location for what we needed"
United States
Ashley A.
$208 nightly
The price is $208
Jun 21 - Jun 22
Total with taxes and fees
The Diamond House

Your Home Away From Home l Conveniently Located

Your Home Away From Home l Conveniently Located
Wooster
10.0 out of 10, Exceptional, (27 reviews)
"Great place to stay!"
United States
Sarah
$275 nightly
The price is $275
Jul 1 - Jul 2
Total with taxes and fees
Your Home Away From Home l Conveniently Located

Charming 3-bedroom cabin in Amish country near Shreve Ohio,great birding area!

Charming 3-bedroom cabin in Amish country near Shreve Ohio,great birding area!
Shreve
9.8 out of 10, Exceptional, (17 reviews)
"Great place to stay and relax while exploring Millersburg and Berlin. Would most definitely stay again when visiting the area."
United States
Colby H.
$264 nightly
The price is $269
Jun 21 - Jun 22
Total with taxes and fees
Charming 3-bedroom cabin in Amish country near Shreve Ohio,great birding area!

Dirt Road Digs - Quiet Home in Lakeville!

Dirt Road Digs - Quiet Home in Lakeville!
3.0 star property
Lakeville
$309 nightly
The price is $317
Jun 21 - Jun 22
Total with taxes and fees
Dirt Road Digs - Quiet Home in Lakeville!

Ideal for traveling professionals. Private 2-bedroom home in peaceful Mansfield.

Ideal for traveling professionals. Private 2-bedroom home in peaceful Mansfield.
Mansfield
9.8 out of 10, Exceptional, (6 reviews)
"The house was perfect for 2 travelers. Extra amenities were great(above and beyond normal). Great place to de-stress and relax."
United States
Carole
$227 nightly
The price is $227
Jul 7 - Jul 8
Total with taxes and fees
Ideal for traveling professionals. Private 2-bedroom home in peaceful Mansfield.

Modern Studio with BBQ Grill and Patio

Modern Studio with BBQ Grill and Patio
Creston
$240 nightly
The price is $240
Jun 21 - Jun 22
Total with taxes and fees
Modern Studio with BBQ Grill and Patio

‘Dirt Road Digs’ - Quiet Home in Lakeville!

‘Dirt Road Digs’ - Quiet Home in Lakeville!
Lakeville
$315 nightly
The price is $323
Jun 21 - Jun 22
Total with taxes and fees
‘Dirt Road Digs’ - Quiet Home in Lakeville!

Recovery Loft 1-bedroom apartment in Mansfield with WiFi, AC, Full Kitchen

Recovery Loft 1-bedroom apartment in Mansfield with WiFi, AC, Full Kitchen
Mansfield
10.0 out of 10, Exceptional, (7 reviews)
"So clean and quiet, with lots of little perks. Very close to the hospital if that is the reason for your stay. The only down side was the steep stairs so not recommended for those who struggle with stairs or the elderly."
United States
Lisa G.
$139 nightly
The price is $139
Jun 22 - Jun 23
Total with taxes and fees
Recovery Loft 1-bedroom apartment in Mansfield with WiFi, AC, Full Kitchen

The Mohican Schoolhouse

The Mohican Schoolhouse
Hanover Township
10.0 out of 10, Exceptional, (12 reviews)
"Excellent stay, felt like home!"
United States
Greg S.
$323 nightly
The price is $330
Jun 24 - Jun 25
Total with taxes and fees
The Mohican Schoolhouse
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.
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Top Ashland Hotel Reviews

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $139 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we give you a choice of vacation rentals close to top attractions in Ashland, or you can go with a more remote option if you're looking for a relaxing stay. Ashland is known for its university setting and jazz scene. Make sure you have time to check out the football games while you're in the area.

What are some of the best vacation home rentals that Ashland has to offer?

Relax, Unwind & Take in the Gorgeous Scenery at Pinehill Hideaway!: Visitors like this Ashland vacation home rental. It is located next to a golf course and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Ashland?

With 14 Expedia vacation rentals, you're sure to find just the right place for your Ashland stay.

What can I see and do in Ashland?

Cultural attractions include Hugo Young Theatre and Guy C. Myers Memorial Band Shell, whereas Mohican River and Audubon Wetlands Preserve are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Byers Woods and Ashland City Hall.

What are vacation rentals like in Ashland?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Ashland. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for small groups.