Ashland Holiday Rentals

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Our top choices for Ashland holiday rentals

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (326)
"Good place"
United States
Elijah
The price is NZ$344
includes taxes & fees
23 Dec - 24 Dec
Maverick Suites at 28 Fenway

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1143)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel

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, (154)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
8.2 out of 10, Very good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
Maverick Suites at 89 Marion

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (133)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
Maverick Suites at 400 Columbus Ave

Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (224)
"The room are ideal and comfortable, there was no smoke smell. It was a cozy stay. The price was affordable too. "
United States
Jeff
Residences at Solomon Pond

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is NZ$637
includes taxes & fees
17 Dec - 18 Dec
Charlesgate Suites

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is NZ$612
includes taxes & fees
5 Jan - 6 Jan 2026
The Chester Hotel

Lovely 3 bedroom 2 bath “6 miles from downtown”

Lovely 3 bedroom 2 bath “6 miles from downtown”
Dorchester
8.2 out of 10, Very good, (10)
"The host was very responsive and the unit has everything you can think of to feel comfortable for your stay. Clean and very beautiful home. 10/10 experience I would highly recommend and book this unit again."
United States
Vey B.
Lovely 3 bedroom 2 bath “6 miles from downtown”

Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!
Hyde Park
9.6 out of 10, Exceptional, (25)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
United States
TIARA V.
The price is NZ$668
includes taxes & fees
17 Dec - 18 Dec
Hidden Gem right in the city of Boston!

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train
Hyde Park
10.0 out of 10, Exceptional, (17)
"Lots of thoughtful touches, enjoyable spot for us to land while visiting Boston."
United States
Wendy K.
Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
2.0 star property
West Cambridge
8.6 out of 10, Excellent, (29)
"Everything was great! We had a really fun stay and the place was perfect for what we needed! "
United States
millie p.
The price is NZ$406
includes taxes & fees
17 Dec - 18 Dec
Great Apartment on River/ Harvard Square two blocks

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
2.0 star property
West Cambridge
8.2 out of 10, Very good, (30)
"Great place to stay! We loved our time there!"
United States
Melody
The price is NZ$375
includes taxes & fees
18 Dec - 19 Dec
On River/Harvard Sq. two blocks

Beautiful studio in historic neighborhood of Boston. Super close to downtown!

Beautiful studio in historic neighborhood of Boston. Super close to downtown!
Roxbury
9.8 out of 10, Exceptional, (46)
"I loved the location. It was convenient to everything I wanted to do. Madhouse Cafe being in walking distance was a phenomenal find."
United States
Marsha G.
Beautiful studio in historic neighborhood of Boston. Super close to downtown!

NEW! Boston Condo Near MBTA, 3Mi to Fenway ! (U3)

NEW! Boston Condo Near MBTA, 3Mi to Fenway ! (U3)
Roxbury
8.8 out of 10, Excellent, (6)
"The house was clean. The house had all of the basic supplies. "
United States
Pam H.
NEW! Boston Condo Near MBTA, 3Mi to Fenway ! (U3)

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Fenway–Kenmore
10.0 out of 10, Exceptional, (74)
"Perfect location for large groups."
United States
Jason Y.
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Modern 2br with W/D in unit, Parking, central air

Modern 2br with W/D in unit, Parking, central air
Roslindale
10.0 out of 10, Exceptional, (62)
"Lots of room and great location! Wonderful stay!"
United States
Amy C.
Modern 2br with W/D in unit, Parking, central air

Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T
Roxbury
9.4 out of 10, Exceptional, (19)
"The vrbo was very clean and as pictured. Very happy with my stay and would stay again. "
United States
Brenden T.
Clean, Contemporary Escape | Near T

558/3 - 3BR Boston - Modern Nest near Franklin Park

558/3 - 3BR Boston - Modern Nest near Franklin Park
Dorchester
9.2 out of 10, Wonderful, (7)
"Great clean place to stay!"
United States
Madeleine D.
The price is NZ$617
includes taxes & fees
17 Dec - 18 Dec
558/3 - 3BR Boston - Modern Nest near Franklin Park
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 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 NZ$344 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?

Hidden Gem right in the city of Boston!: This holiday home rental outside of Ashland is located near skiing, and offers a selection of games, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.