Ashland Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Ashland vacation rentals

Private kitchen

Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
Ashland
$280 nightly
The price is $296
May 10 - May 11
Total with taxes and fees
Charming 3-bedroom house in delightful Ashland for your getaway
Premium Apartment | Living area | 24-inch Smart TV with digital channels

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
$330 nightly
The price is $379
May 8 - May 9
Total with taxes and fees
The Chester Hotel
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,186 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
$133 nightly
The price is $149
May 10 - May 11
Total with taxes and fees
Crescent Suites Hotel
Interior

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)
$551 nightly
The price is $648
May 12 - May 13
Total with taxes and fees
Luxury Home located in Back Bay 8min walk to Fewnway Park, close to Boston University, Berklee & MIT
TV

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
$371 nightly
The price is $436
May 10 - May 11
Total with taxes and fees
Charming 1 Bedroom | Newbury Street
Living area

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
$270 nightly
The price is $309
May 10 - May 11
Total with taxes and fees
On River/Harvard Sq. two blocks
Smart TV, fireplace

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.
$1,136 nightly
The price is $1,305
May 10 - May 11
Total with taxes and fees
Large victorian home 15 mins from downtown lots of local restaurants and bars
Exterior

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
$274 nightly
The price is $315
May 10 - May 11
Total with taxes and fees
Maverick Suites at 245 Newbury St
Outdoor dining

🎖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.
$399 nightly
The price is $459
May 11 - May 12
Total with taxes and fees
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dining

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.
$474 nightly
The price is $529
May 9 - May 10
Total with taxes and fees
Relax with family or friends to this elegant apartment in the heart of Waltham
Oven, stovetop, dishwasher, coffee/tea maker

South End Serene Studio

South End Serene Studio
Back Bay
$291 nightly
The price is $339
May 11 - May 12
Total with taxes and fees
South End Serene Studio
Outdoor dining

🎖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.
$363 nightly
The price is $417
May 10 - May 11
Total with taxes and fees
🎖The Boiler Room - Close to Subway & Downtown🎖
TV, offices

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.
$480 nightly
The price is $552
May 10 - May 11
Total with taxes and fees
The Chester: Penthouse One Bedroom
TV

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.
$376 nightly
The price is $420
May 11 - May 12
Total with taxes and fees
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
1 bedroom, WiFi

Compact Back Bay Studio

Compact Back Bay Studio
Back Bay
$235 nightly
The price is $276
May 10 - May 11
Total with taxes and fees
Compact Back Bay Studio
Interior

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.
$639 nightly
The price is $735
May 11 - May 12
Total with taxes and fees
Spacious 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View
TV

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
$333 nightly
The price is $383
May 10 - May 11
Total with taxes and fees
Modern 3BR nest near Franklin Park 558/2
Apartment, 2 Bedrooms | Interior

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
$238 nightly
The price is $274
May 8 - May 9
Total with taxes and fees
Furnished Apts near Harvard Stadium
Interior

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.
$890 nightly
The price is $994
May 11 - May 12
Total with taxes and fees
Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.
2 bedrooms, iron/ironing board, WiFi

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.
$239 nightly
The price is $267
May 10 - May 11
Total with taxes and fees
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

citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Hands down my favorite hotel chain. Only disappointment was that the website implies that the kitchen is available 24/7, but it actually meant that snacks were available 24/7. Otherwise, my stay was great! Staff is friendly & helpful, the location is ideal, & the views are beautiful."
Cristina 1-night trip
Posted 3 hours ago
citizenM Boston Back Bay

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 $130 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

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.