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 AU$411
includes taxes & fees
10 June - 11 June
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 AU$495
includes taxes & fees
7 June - 8 June
The Chester Hotel

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"It was a great stay!"
United States
Adina S.
The price is AU$386
includes taxes & fees
4 June - 5 June
Light-filled Studio | Back Bay

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is AU$461
includes taxes & fees
7 June - 8 June
Beautiful 1BR near Fenway Park + Kenmore!

Tranquil South End Studio

Tranquil South End Studio
Back Bay
The price is AU$389
includes taxes & fees
8 June - 9 June
Tranquil South End Studio

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (370 reviews)
"Great stay. "
United States
Anna
The price is AU$362
includes taxes & fees
7 June - 8 June
Maverick Suites at 28 Fenway

Symple Live

Symple Live
4.0 star property
Fenway–Kenmore
8.0 out of 10, Very good, (1 review)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is AU$455
includes taxes & fees
9 June - 10 June
Symple Live

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

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
8.8 out of 10, Excellent, (5 reviews)
"Great place for our overnight stay. Red line was close by to get us in and out of Boston. Host was incredibly responsive. She suggested a restaurant close by, via Cannuccia.. stunning pastries on the weekend. "
United States
Ingrid
The price is AU$286
includes taxes & fees
9 June - 10 June
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.4 out of 10, Very good, (21 reviews)
"Friendly hosts"
United States
Jan
The price is AU$301
includes taxes & fees
4 June - 5 June
Free Parking at 1 Bed Basement Apt, Near BU & MIT

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (80 reviews)
"Beautiful property and rooms. "
Canada
Dawn W.
The price is AU$557
includes taxes & fees
15 June - 16 June
🎖The Boiler Room - Close to Subway & Downtown🎖

Stellar South End Studio

Stellar South End Studio
Back Bay
The price is AU$395
includes taxes & fees
4 June - 5 June
Stellar South End Studio

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (152 reviews)
"The property is clean and for the money, is a win for the visitor. "
United States
Ramon S
The price is AU$310
includes taxes & fees
11 June - 12 June
Maverick Suites at 400 Columbus Ave

Artisan Studio with Exposed Brick

Artisan Studio with Exposed Brick
Back Bay
The price is AU$358
includes taxes & fees
21 June - 22 June
Artisan Studio with Exposed Brick

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 AU$376
includes taxes & fees
7 June - 8 June
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

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, (26 reviews)
"Everything was fine, place is clean and convenient"
United States
Tyson P.
The price is AU$291
includes taxes & fees
8 June - 9 June
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

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, (169 reviews)
"Great place for a solo business trip. Great location"
United States
Eleazar
The price is AU$478
includes taxes & fees
7 June - 8 June
Maverick Suites at 245 Newbury St

Stunning 1BR | Steps to Fenway!

Stunning 1BR | Steps to Fenway!
Fenway–Kenmore
The price is AU$583
includes taxes & fees
7 June - 8 June
Stunning 1BR | Steps to Fenway!

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, (36 reviews)
"Clean apartment. Close to Harvard Square. Stairs not user-friendly."
United States
Jeffrey
The price is AU$448
includes taxes & fees
7 June - 8 June
Great Apartment on River/ Harvard Square two blocks

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
The price is AU$551
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
8.8 out of 10, Excellent, (11 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 AU$577
includes taxes & fees
1 July - 2 July
Stylish Back Bay Retreat, Steps from Prudential
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 favourite 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 depend 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 AU$223 per night. Entering your travel dates in the search wizard might find you 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 2BR Fort Hill Apartment | Near the 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 Massachusetts Horticultural Society's Gardens at Elm Bank, 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 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.