A river winding through a forest with autumn foliage.

Ashland Holiday Rentals

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Our top choices for Ashland holiday rentals

Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"This is our second stay here and both times have been good. The house is quiet, even for it being on a well traveled road. "
United States
John W.
The price is NZ$522
includes taxes & fees
5 July - 6 July
Charming 3-bedroom house in delightful Ashland for your getaway

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is NZ$550
includes taxes & fees
30 June - 1 July
The Chester Hotel

The Concord Hotel

The Concord Hotel
2.0 star property
South End
10.0 out of 10, Exceptional, (1 review)
"Overall had a great experience here. Took just a couple minutes texting the host to get the check in information that was to be emailed- but they sent it pretty quickly when I said it wasn't sent yet. I didn't need anything else from the host. It was clean and overall pretty nice! The stairs you take to get up to the room are pretty loud, so I woke up one time when other people got home to other rooms during my stay, but that was it! Overall good. I was there for a holiday weekend so the price...
United States
Jessica
The price is NZ$562
includes taxes & fees
29 June - 30 June
The Concord Hotel

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (6 reviews)
The price is NZ$557
includes taxes & fees
30 June - 1 July
Symple Live

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,223 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is NZ$308
includes taxes & fees
12 July - 13 July
Crescent Suites Hotel

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (176 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is NZ$239
includes taxes & fees
30 June - 1 July
Maverick Suites at 245 Newbury St

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
The price is NZ$533
includes taxes & fees
30 June - 1 July
Charming 1 Bedroom | Newbury Street

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
9.0 out of 10, Wonderful, (12 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
The price is NZ$541
includes taxes & fees
1 July - 2 July
Stylish Back Bay Retreat, Steps from Prudential

The Chester: Hip, Renovated, South End

The Chester: Hip, Renovated, South End
South End
10.0 out of 10, Exceptional, (2 reviews)
"Nice room. Good location "
United States
Abenamar A.
The Chester: Hip, Renovated, South End

Modern Luxury 2BR | King + Queen | Suite 8

Modern Luxury 2BR | King + Queen | Suite 8
Fenway–Kenmore
10.0 out of 10, Exceptional, (2 reviews)
"This is a beautiful, newly refurbished property in the heart of downtown Boston. It is extremely convenient and walkable to almost everything - just a couple of blocks to Fenway, the Museum of Fine Art, and Newbury Street. We enjoyed being so close to so many things and definitely got our steps in! The apartment had everything we needed, was beautiful and clean, and impressively maximized the small space. The bedding was soft, and the beds were super comfortable. We appreciated having a fully...
United States
Dawn F.
The price is NZ$845
includes taxes & fees
8 July - 9 July
Modern Luxury 2BR | King + Queen | Suite 8

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (157 reviews)
"Great location!"
United States
Kevin
The price is NZ$286
includes taxes & fees
30 June - 1 July
Maverick Suites at 400 Columbus Ave

The only 4 Bedroom Apartment w/ Roofdeck in Boston! 8min from Fenway Park, close to universities!

The only 4 Bedroom Apartment w/ Roofdeck in Boston! 8min from Fenway Park, close to universities!
Fenway–Kenmore
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely perfect for a traveling family to spread out in. "
United States
Jered D.
The price is NZ$1,613
includes taxes & fees
23 July - 24 July
The only 4 Bedroom Apartment w/ Roofdeck in Boston! 8min from Fenway Park, close to universities!

Tranquil South End Studio

Tranquil South End Studio
Back Bay
The price is NZ$558
includes taxes & fees
2 July - 3 July
Tranquil South End Studio

Compact Back Bay Studio

Compact Back Bay Studio
Back Bay
The price is NZ$600
includes taxes & fees
30 June - 1 July
Compact Back Bay Studio

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very good, (45 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is NZ$554
includes taxes & fees
30 June - 1 July
On River/Harvard Sq. two blocks

Newly renovated pet friendly apt by parks and train!

Newly renovated pet friendly apt by parks and train!
Roxbury
8.0 out of 10, Very good, (40 reviews)
"Great location and very accommodating host. House was clean, beds extremely comfortable. Best of urban location with lovely home feel! On street parking was a dream and easy to get into downtown Boston, 93 or 128. Many great restaurants to enjoy in JP. Would definitely stay again. "
United States
Lisa L.
Newly renovated pet friendly apt by parks and train!

Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.4 out of 10, Very good, (37 reviews)
"Clean apartment. Close to Harvard Square. Stairs not user-friendly."
United States
Jeffrey
The price is NZ$564
includes taxes & fees
30 June - 1 July
Great Apartment on River/ Harvard Square two blocks

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
8.0 out of 10, Very good, (1 review)
"Although we enjoyed the property, the pics were deceiving."
United States
Barry G.
The price is NZ$776
includes taxes & fees
29 July - 30 July
Beautiful 1BR near Fenway Park + Kenmore!

Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.4 out of 10, Exceptional, (22 reviews)
"Beds were comfortable, location was convenient for our needs, thankful for the shoveling and clearing of snow in the morning! "
United States
Stephanie G.
The price is NZ$394
includes taxes & fees
5 July - 6 July
Charming 2-bedroom apartment with WiFi, AC in superb Canton

Cozy Studio in the South End

Cozy Studio in the South End
Back Bay
The price is NZ$446
includes taxes & fees
1 July - 2 July
Cozy Studio in the South End
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 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 NZ$239 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?

Charming 3-bedroom house in delightful Ashland for your getaway: This highly rated holiday home rental in Ashland comes with laundry facilities so that you can feel at home during your trip.

How many holiday rentals are there in Ashland?

Expedia has 3 holiday rentals for your stay in Ashland.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Apex Entertainment Center, or get outside and enjoy nature at Framingham Town Common. 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.