Ashland Holiday Rentals from €136: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Ashland has to offer?

Cozy Apartment | Near T : This holiday home rental outside of Ashland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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Our top choices for Ashland holiday rentals

Charming 3-bedroom house in delightful Ashland for your getaway

Ashland

includes taxes & fees

20 Apr - 21 Apr

The Chester Hotel

South End

Yanmarie

includes taxes & fees

21 Apr - 22 Apr

Blissful South End Studio

Back Bay

Penelope D.

includes taxes & fees

22 Apr - 23 Apr

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Fenway–Kenmore

Mai

includes taxes & fees

26 Apr - 27 Apr

Serene South End Studio

Back Bay

Dylan S.

includes taxes & fees

25 Apr - 26 Apr

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Lincoln

Tyson P.

includes taxes & fees

20 Apr - 21 Apr

Maverick Suites at 28 Fenway

Fenway–Kenmore

Kristin

includes taxes & fees

21 Apr - 22 Apr

2 bedrooms, desk, iron/ironing board, WiFi

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Fenway–Kenmore

Matthew G.

includes taxes & fees

26 Apr - 27 Apr

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Top Ashland Hotel Reviews

Copley Square Hotel, a FOUND Hotel

10/10 Excellent

"I recommend The Copley Square Hotel. It’s the cutest boutique style hotel EVER! The room was quaint and cozy. The location was perfect. All staff I encountered were friendly and polite. I could go on and on …"

The Midtown Hotel MOD Collection by Sonesta

2/10 Terrible

"Checked in April 14th 2026. The weather in Boston was Sunny and 78. Noticed the lobby checking in was very stuffy and hot. Get to the room and it’s no better. Turning the dials and switches on what appeared to be an older climate control system did nothing. No cooling or heat. Called the front desk and they told me to do what I’d already done. I then went to the lobby to inquire and was told that “corporate hasn’t activated the A/C system. Opening the window would be your best bet.” Unacceptable. I asked for number and called the corporate offices. Was told basically what the staff had said. The A/C system “wasn’t turned on yet” because it was April and not “hot enough out yet” to do so. I’ve never heard of such a thing. It wasn’t inoperable, They just wouldn’t turn it on. They offered no compensation nor did the staff in any capacity. Absurd. Hotels.com customer service contacted the property and said the property was willing to give us a refund only if we checked out immediately. No offer to help us find other accommodations. Just check out and take your money. Now I’m with my family in Boston scrambling to find a room at the last minute and there is absolutely nothing. We had no choice but to stay, the climate system never became functional, the temperature in the room was ridiculously warm, we had to keep the small vertical window open to the sounds of sirens and people speaking in the parking lot at 4 o’clock in the morning. It was an absolute nightmare. Ruined the trip."

Copley House

8/10 Good

"A favorite place to stay in Boston. Sweet location, close to the T, private, comfy, well-maintained and managed. Usually very quiet, though this particular stay was in a unit with thin walls/floors that allowed considerable noise that made it hard to sleep after housekeeping o'clock. Street and neighborhood are very quiet. "

Find out more about Ashland

Everything you need to know about Ashland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland holiday rentals we have selected for you start as low as €136 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland holiday 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 holiday.

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.

Frequently asked questions

Are there holiday rentals in Ashland?

Yes, there are holiday rentals close to the most popular sights in Ashland, or you can select a more secluded option if you're looking for a relaxing stay. Ashland is known for its shopping and restaurants. Make sure you have time to check out the lake views while you're in the area.

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

Cozy Apartment | Near T: This holiday home rental outside of Ashland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Fun and Games Family Entertainment Center, or get outside and enjoy nature at Cochituate State Park. Other places in town to visit include Ashland State Park and Hopkinton State Park.

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for families.

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Our top choices for Ashland holiday rentals