Ashland Vacation Rentals

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Our top choices for Ashland vacation 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, (1 review)
"Our stay was very nice, in that there is plenty of space and the shared areas and bedrooms are large spaces. Communication with the host went well, as we needed to get the correct door code to access, and there was a small issue with the thermostat which the host addressed quickly."
United States
John W.
The price is CA $185
CA $403 total
includes taxes & fees
May 11 - May 12
Charming 3-bedroom house in delightful Ashland for your getaway

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is CA $284
CA $500 total
includes taxes & fees
May 18 - May 19
The Chester Hotel

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,189 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is CA $188
CA $210 total
includes taxes & fees
Jun 7 - Jun 8
Crescent Suites Hotel

Luxury Home located in Back Bay 8min walk to Fewnway Park, close to Boston University, Berklee & MIT

Luxury Home located in Back Bay 8min walk to Fewnway Park, close to Boston University, Berklee & MIT
Fenway–Kenmore
10.0 out of 10, Exceptional, (1 review)
The price is CA $473
CA $894 total
includes taxes & fees
May 18 - May 19
Luxury Home located in Back Bay 8min walk to Fewnway Park, close to Boston University, Berklee & MIT

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
The price is CA $295
CA $590 total
includes taxes & fees
May 20 - May 21
Charming 1 Bedroom | Newbury Street

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very good, (41 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is CA $233
CA $431 total
includes taxes & fees
May 11 - May 12
On River/Harvard Sq. two blocks

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

Large victorian home 15 mins from downtown lots of local restaurants and bars
Mattapan
8.6 out of 10, Excellent, (8 reviews)
"The house was as advertised as far as what was seen in the pictures. Some of the light bulbs/fixtures were not operational, but the house as a whole was very clean and accommodating. Communication with the host was quick and straightforward. "
United States
Myles H.
The price is CA $880
CA $1,785 total
includes taxes & fees
May 17 - May 18
Large victorian home 15 mins from downtown lots of local restaurants and bars

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, (166 reviews)
"Great location. Well priced. Its appeals to a specific type of traveler. Overall clean, quiet, solid WiFi services. I had some initial challenges getting in the building, but that was my fault for not checking in and providing the required documents. I would definitely stay again. PS The pizza place right across the street makes a great thin crust pie. "
United States
James
The price is CA $309
CA $481 total
includes taxes & fees
May 31 - Jun 1
Maverick Suites at 245 Newbury St

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
9.8 out of 10, Exceptional, (110 reviews)
"Great place for a short stay. It was clean and cozy, just as described in the listing. The check-in process was very easy and The host was very responsive. Highly recommend."
United States
Phalone P.
The price is CA $272
CA $627 total
includes taxes & fees
May 11 - May 12
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

Relax with family or friends to this elegant apartment in the heart of Waltham

Relax with family or friends to this elegant apartment in the heart of Waltham
South Side
9.6 out of 10, Exceptional, (19 reviews)
"Comfortable for 5 adults, no problems, as advertised, would rent again. "
United States
Brian K.
The price is CA $301
CA $733 total
includes taxes & fees
May 11 - May 12
Relax with family or friends to this elegant apartment in the heart of Waltham

South End Serene Studio

South End Serene Studio
Back Bay
The price is CA $167
CA $421 total
includes taxes & fees
May 11 - May 12
South End Serene Studio

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (77 reviews)
"Beautiful property and rooms. "
Canada
Dawn W.
🎖The Boiler Room - Close to Subway & Downtown🎖

The Chester: Penthouse One Bedroom

The Chester: Penthouse One Bedroom
South End
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely loved my stay. Great location, beautiful place. Clean and bright. We will be back!"
United States
Linda C.
The price is CA $684
CA $1,089 total
includes taxes & fees
May 24 - May 25
The Chester: Penthouse One Bedroom

Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking

Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
Ward Two
9.8 out of 10, Exceptional, (14 reviews)
"Overall, comfortable and well located. Host was quick to respond with any questions we had. "
United States
AJ V.
The price is CA $260
CA $586 total
includes taxes & fees
May 21 - May 22
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking

Compact Back Bay Studio

Compact Back Bay Studio
Back Bay
The price is CA $211
CA $444 total
includes taxes & fees
May 21 - May 22
Compact Back Bay Studio

Spacious 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View

Spacious 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View
Dorchester
10.0 out of 10, Exceptional, (12 reviews)
"We loved this home. It was clean, well equipped and very well located for our family of 8 to visit Boston. Had a great time and loved the house. "
United States
Arlene P.
The price is CA $464
CA $969 total
includes taxes & fees
May 11 - May 12
Spacious 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View

Modern 3BR nest near Franklin Park 558/2

Modern 3BR nest near Franklin Park 558/2
Dorchester
10.0 out of 10, Exceptional, (17 reviews)
"Very nice property, parking is safe, owner give clear checkin and checkout instructions. Very good."
United States
Kevin
The price is CA $195
CA $526 total
includes taxes & fees
May 11 - May 12
Modern 3BR nest near Franklin Park 558/2

Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
9.0 out of 10, Wonderful, (11 reviews)
"Great property. Very clean and spacious. Easy 15 minutes walk to Harvard. Easy check in and check out process"
United States
Tho
The price is CA $295
CA $496 total
includes taxes & fees
May 11 - May 12
Furnished Apts near Harvard Stadium

Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.

Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.
Stoughton
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful for family. "
United States
Karen C.
The price is CA $799
CA $1,360 total
includes taxes & fees
May 11 - May 12
Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.2 out of 10, Wonderful, (11 reviews)
"Very easy and accommodating stay right outside of the city. Would recommend for a stay. "
United States
Nolan B.
The price is CA $185
CA $367 total
includes taxes & fees
May 11 - May 12
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Ashland?

Yes, you can find vacation rentals near top local attractions in Ashland, or you can go with a more secluded option if you're looking for relaxation. 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 vacation rentals that Ashland has to offer?

Cozy Apartment | Near T: Visitors like this Ashland vacation home rental. It 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 vacation rentals like in Ashland?

Vacation rentals are private properties you can reserve for a couple days or more in Ashland. Vacation rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.