Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is CA $178
CA $449 total
includes taxes & fees
Apr 1 - Apr 2
The Chester Hotel

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very good, (10 reviews)
"Amazing location for the price. Check-in was super easy with clear instructions. Free parking was such a great perk for Boston. As for the house, despite a few visual damages (and 2 lightbulbs for the lamps not working), there was not much to complain about. Would recommend "
United States
Mai
The price is CA $130
CA $296 total
includes taxes & fees
Mar 26 - Mar 27
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Blissful South End Studio

Blissful South End Studio
Back Bay
The price is CA $103
CA $303 total
includes taxes & fees
Apr 13 - Apr 14
Blissful South End Studio

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 price is CA $149
CA $447 total
includes taxes & fees
Mar 25 - Mar 26
The Chester: Hip, Renovated, South End

Unique South End Studio

Unique South End Studio
Back Bay
The price is CA $103
CA $305 total
includes taxes & fees
Apr 1 - Apr 2
Unique South End Studio

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.4 out of 10, Very good, (8 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
The price is CA $167
CA $404 total
includes taxes & fees
Mar 25 - Mar 26
Stylish Back Bay Retreat, Steps from Prudential

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

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Lincoln
10.0 out of 10, Exceptional, (23 reviews)
"We had a fabulous time! It was nice to be able to travel with the dogs and having the fenced yard made it great for the dogs. We were able to visit all our relatives w/o displacing anyone, like before.We will be coming back!"
United States
VERNE W.
The price is CA $150
CA $285 total
includes taxes & fees
Mar 25 - Mar 26
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

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, (13 reviews)
"Nice visit"
United States
Nate P.
The price is CA $182
CA $487 total
includes taxes & fees
Mar 25 - Mar 26
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.0 out of 10, Wonderful, (2 reviews)
"Easy check-in, and the host was available to assist with any needs. Space was nice and cozy. Also, the view from the top floor was pretty dope. Will definitely book again."
United States
Breshan B.
The price is CA $162
CA $267 total
includes taxes & fees
Mar 30 - Mar 31
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

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, (160 reviews)
"Great location, clean and great 😌 "
United States
Catherine
Maverick Suites at 245 Newbury St

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
The price is CA $207
CA $739 total
includes taxes & fees
Mar 30 - Mar 31
The only 4 Bedroom Apartment w/ Roofdeck in Boston! 8min from Fenway Park, close to universities!

3BR Dorchester Boston, Free Parking, Pet-Friendly, Near Franklin Park - 558/1

3BR Dorchester Boston, Free Parking, Pet-Friendly, Near Franklin Park - 558/1
Dorchester
9.0 out of 10, Wonderful, (11 reviews)
"Had a great stay! The apartment was nice and the host was flexible and accommodating. I would recommend."
United States
Andrew M.
The price is CA $148
CA $412 total
includes taxes & fees
Mar 30 - Mar 31
3BR Dorchester Boston, Free Parking, Pet-Friendly, Near Franklin Park - 558/1

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, (30 reviews)
"Perfect location for Head of the Charles Regatta!"
United States
Kristy R.
The price is CA $159
CA $339 total
includes taxes & fees
Mar 27 - Mar 28
Great Apartment on River/ Harvard Square two blocks

NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (51 reviews)
"Pefect location for us to be near family. Hosts were extremely accomodating and apartment had every little detail provided for. We would absolutely stay again!"
United States
Sherry K.
The price is CA $122
CA $244 total
includes taxes & fees
Mar 25 - Mar 26
NEW Modern Apartment Near Boston & Harvard Square.

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (4 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
The price is CA $178
CA $293 total
includes taxes & fees
Mar 29 - Mar 30
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

4BR Pet-Friendly Home w/ 4 Parking Randolph - 17

4BR Pet-Friendly Home w/ 4 Parking Randolph - 17
Randolph
10.0 out of 10, Exceptional, (4 reviews)
"It was a cozy and clean home with everything needed to accommodate your stay. My family and young nephews had a great time here and I’d recommend it to anyone looking to visit Boston"
United States
Nicholas P.
The price is CA $135
CA $416 total
includes taxes & fees
Mar 26 - Mar 27
4BR Pet-Friendly Home w/ 4 Parking Randolph - 17

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

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.0 out of 10, Wonderful, (9 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 $368 total
includes taxes & fees
Apr 10 - Apr 11
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

14/1 - 3BR Milton - Cozy Apt near Blue Hills Museum

14/1 - 3BR Milton - Cozy Apt near Blue Hills Museum
Milton
9.4 out of 10, Exceptional, (11 reviews)
"Just as lovely in person as in the pictures! Host was quick to respond to questions and very proactive with check in procedure. Wish we could have stayed longer!"
United States
Johnna K.
The price is CA $135
CA $359 total
includes taxes & fees
Mar 25 - Mar 26
14/1 - 3BR Milton - Cozy Apt near Blue Hills Museum

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (340 reviews)
"Good place"
United States
Elijah
The price is CA $143
CA $299 total
includes taxes & fees
Mar 30 - Mar 31
Maverick Suites at 28 Fenway

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

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.8 out of 10, Exceptional, (18 reviews)
"Overall comfortable stay"
United States
Jolly J.
The price is CA $221
CA $282 total
includes taxes & fees
Apr 12 - Apr 13
Charming 2-bedroom apartment with WiFi, AC in superb Canton
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 Hopkinton State Park and Ashland 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.