Photo by Swetha Srinivasan

Ashland Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Ashland

Our top choices for Ashland holiday rentals

Maverick Suites at 28 Fenway

3.0 star property
8.8 out of 10, Excellent, (264)
"Great location"
The price is NZ$366
includes taxes & fees
23 Sept - 24 Sept
Maverick Suites at 28 Fenway

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (1075)
"Very pleased with hotel. "
Crescent Suites Hotel

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very good, (518)
"Great hotel!"
The price is NZ$567
includes taxes & fees
22 Sept - 23 Sept
907 Main Hotel Central Square, Sonder by Marriott Bonvoy

Maverick Suites at 89 Marion

2.0 star property
8.4 out of 10, Very good, (251)
"I liked the location very much! "
The price is NZ$398
includes taxes & fees
2 Oct - 3 Oct
Maverick Suites at 89 Marion

The Chester Hotel

4.0 star property
9.0 out of 10, Wonderful, (19)
"Great place to stay in Boston and near colleges."
The price is NZ$787
includes taxes & fees
21 Sept - 22 Sept
The Chester Hotel

Maverick Suites at 245 Newbury St

2.0 star property
8.2 out of 10, Very good, (139)
"Clean. Great location. "
The price is NZ$547
includes taxes & fees
5 Oct - 6 Oct
Maverick Suites at 245 Newbury St

Residences at Solomon Pond

3.5 star property
8.2 out of 10, Very good, (198)
"The property is clean and spacious. Quiet place."
Residences at Solomon Pond

Charlesgate Suites

3.5 star property
9.4 out of 10, Exceptional, (186)
"Awesome property, conveniently located near everything, especially Fenway. Definitely will stay here again. "
The price is NZ$788
includes taxes & fees
11 Sept - 12 Sept
Charlesgate Suites

No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

4.0 star property
9.4 out of 10, Exceptional, (933)
"Beautiful property "
The price is NZ$570
includes taxes & fees
21 Sept - 22 Sept
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

Maverick Suites at 402 Columbus Ave

2.5 star property
7.8 out of 10, Good, (60)
"Easy to walk to and from T stations near by. Decently priced and was overall a great place to stay!"
The price is NZ$569
includes taxes & fees
2 Oct - 3 Oct
Maverick Suites at 402 Columbus Ave

Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

3.5 star property
8.8 out of 10, Excellent, (70)
"Great place , size of the apartment , very clean"
The price is NZ$676
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway

4.0 star property
8.8 out of 10, Excellent, (262)
"Great location for a family close to Fenway. Beds were a little hard. "
The price is NZ$597
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway

Maverick Suites at 400 Columbus Ave

2.0 star property
7.4 out of 10, Good, (120)
"Great place to stay with close proximity to the city "
The price is NZ$481
includes taxes & fees
5 Oct - 6 Oct
Maverick Suites at 400 Columbus Ave

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

8.0 out of 10, Very good, (5)
"Great location for a long weekend in Boston! "
The price is NZ$907
includes taxes & fees
11 Sept - 12 Sept
Free Parking at 1 Bed Basement Apt, Near BU & MIT

60/2 SPRING GETAWAY EARLY BIRD 10%! Newly built & stylish apartment in Boston

9.8 out of 10, Exceptional, (8)
"The space looks like it was just renovated. It was clean and had new appliances. The bed rooms all have one bed and a bunk bed. You could really cram a lot of guess in the house. The living space is large with a sectional sofa that can fit 6-8, a kitchen table with room for 6. The parking spots in back are pretty tight, but there was plenty of street parking out front. If you have a bigger vehicle, I'd park out front."
The price is NZ$628
includes taxes & fees
9 Sept - 10 Sept
60/2 SPRING GETAWAY EARLY BIRD 10%! Newly built & stylish apartment in Boston

Large victorian home 15 mins from downtown lots of local restaurants and bars

8.6 out of 10, Excellent, (4)
"Host was quick to respond and helpful. It had very spacious living area. There is a king bed, all the "queen" beds were actually doubles. There were bath towels but no washcloths. There was a Keurig, not coffee maker as advertised. It was sufficient for our two day stay. We had a great visit to Boston. The house location was easy driving to the harbor walk and seaport district. We were able to Uber relatively cheap to Fenway and downtown Boston. It was overall a good experience with this host. ...
The price is NZ$2,084
includes taxes & fees
9 Sept - 10 Sept
Large victorian home 15 mins from downtown lots of local restaurants and bars

Lovely 3 bedroom 2 bath “6 miles from downtown”

9.4 out of 10, Exceptional, (8)
"The host was very responsive and the unit has everything you can think of to feel comfortable for your stay. Clean and very beautiful home. 10/10 experience I would highly recommend and book this unit again."
The price is NZ$1,504
includes taxes & fees
9 Sept - 10 Sept
Lovely 3 bedroom 2 bath “6 miles from downtown”

Great Apartment on River/ Harvard Square two blocks

2.0 star property
9.0 out of 10, Wonderful, (19)
"Great location, everything we needed for Boston Calling!"
The price is NZ$544
includes taxes & fees
9 Sept - 10 Sept
Great Apartment on River/ Harvard Square two blocks

60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston

9.6 out of 10, Exceptional, (14)
"Wonderful stay! I would happily return back to this apartment !! "
The price is NZ$666
includes taxes & fees
9 Sept - 10 Sept
60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

10.0 out of 10, Exceptional, (67)
"Really enjoyed the house. Great location, easy checking in. They even had a decorated Christmas tree for us."
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Find out more about Ashland

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, 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 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?

Hidden Gem right in the city of Boston!: This holiday home rental outside of Ashland is located near skiing, and offers a selection of games, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Hopkinton State Park and Ashland 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.