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Our top choices for Ashland holiday 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 £233
includes taxes & fees
1 Apr - 2 Apr
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 £200
includes taxes & fees
12 Apr - 13 Apr
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Blissful South End Studio

Blissful South End Studio
Back Bay
10.0 out of 10, Exceptional, (1 review)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is £166
includes taxes & fees
1 Apr - 2 Apr
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 £243
includes taxes & fees
29 Mar - 30 Mar
The Chester: Hip, Renovated, South End

Unique South End Studio

Unique South End Studio
Back Bay
The price is £166
includes taxes & fees
1 Apr - 2 Apr
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 £220
includes taxes & fees
29 Mar - 30 Mar
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 £155
includes taxes & fees
6 Apr - 7 Apr
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 £259
includes taxes & fees
1 Apr - 2 Apr
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 £148
includes taxes & fees
31 Mar - 1 Apr
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
The price is £175
includes taxes & fees
30 Mar - 31 Mar
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 £356
includes taxes & fees
29 Mar - 30 Mar
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 £218
includes taxes & fees
30 Mar - 31 Mar
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, (31 reviews)
"Perfect location for Head of the Charles Regatta!"
United States
Kristy R.
The price is £185
includes taxes & fees
27 Mar - 28 Mar
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 £169
includes taxes & fees
7 Apr - 8 Apr
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 £160
includes taxes & fees
6 Apr - 7 Apr
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 £271
includes taxes & fees
29 Mar - 30 Mar
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, (10 reviews)
"Very easy and accommodating stay right outside of the city. Would recommend for a stay. "
United States
Nolan B.
The price is £198
includes taxes & fees
31 Mar - 1 Apr
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton

14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton
Milton
9.4 out of 10, Exceptional, (11 reviews)
"Enjoyable and comfortable, great spot to chill."
United States
Roxana R.
The price is £287
includes taxes & fees
5 Apr - 6 Apr
14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (340 reviews)
"Clean"
United States
Kristin
The price is £158
includes taxes & fees
14 Apr - 15 Apr
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 £154
includes taxes & fees
29 Mar - 30 Mar
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

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, apart-hotels, 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 £120 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?

Cozy Apartment | Near T: This holiday home rental outside of Ashland 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 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.