Ashland Vacation Rentals

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Dec 8 - Dec 9
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Vacation Rentals in Ashland

Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets
Maverick Suites at 28 Fenway

Apartment in Fenway–Kenmore

3.0 star property
8.8 out of 10, Excellent, (322)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
$174 nightly
The price is $201
Jan 8 - Jan 9, 2026
Total with taxes and fees
Maverick Suites at 28 Fenway
Property grounds
Crescent Suites Hotel

Aparthotel in South Side

3.0 star property
9.6 out of 10, Exceptional, (1142)
"Lovely, quiet place."
United States
Fatu
$140 nightly
The price is $157
Dec 19 - Dec 20
Total with taxes and fees
Crescent Suites Hotel
Interior entrance
Maverick Suites at 89 Marion

Aparthotel in Coolidge Corner South Side

2.0 star property
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
$182 nightly
The price is $203
Jan 4 - Jan 5, 2026
Total with taxes and fees
Maverick Suites at 89 Marion
Exterior
Maverick Suites at 245 Newbury St

Aparthotel in Back Bay

2.0 star property
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
$197 nightly
The price is $226
Dec 10 - Dec 11
Total with taxes and fees
Maverick Suites at 245 Newbury St
Business center
Residences at Solomon Pond

Aparthotel in Marlborough

3.5 star property
8.2 out of 10, Very Good, (223)
"The room are ideal and comfortable, there was no smoke smell. It was a cozy stay. The price was affordable too. "
United States
Jeff
$125 nightly
The price is $140
Dec 9 - Dec 10
Total with taxes and fees
Residences at Solomon Pond
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels
Maverick Suites at 402 Columbus Ave

Aparthotel in South End

2.5 star property
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
$193 nightly
The price is $222
Dec 9 - Dec 10
Total with taxes and fees
Maverick Suites at 402 Columbus Ave
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Aparthotel in South End

2.0 star property
7.4 out of 10, Good, (133)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
$172 nightly
The price is $198
Dec 16 - Dec 17
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Aparthotel in Fenway–Kenmore

3.5 star property
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
$310 nightly
The price is $356
Dec 10 - Dec 11
Total with taxes and fees
Charlesgate Suites
City Studio | Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel

Aparthotel in South End

4.0 star property
8.6 out of 10, Excellent, (28)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
$308 nightly
The price is $355
Dec 10 - Dec 11
Total with taxes and fees
The Chester Hotel
Dining
On River/Harvard Sq. two blocks

Apartment in West Cambridge

2.0 star property
8.2 out of 10, Very Good, (30)
"Great place to stay! We loved our time there!"
United States
Melody
$200 nightly
The price is $229
Dec 9 - Dec 10
Total with taxes and fees
On River/Harvard Sq. two blocks
TV, fireplace
Lovely 3 bedroom 2 bath “6 miles from downtown”

Apartment in 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”
Interior
Hidden Gem right in the city of Boston!

Vacation Home in Hyde Park

9.6 out of 10, Exceptional, (24)
"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.
$339 nightly
The price is $389
Dec 16 - Dec 17
Total with taxes and fees
Hidden Gem right in the city of Boston!
Outdoor dining
Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

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

Apartment in Roxbury

9.8 out of 10, Exceptional, (45)
"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!
Fridge, microwave, oven, stovetop
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Vacation Home in Fenway–Kenmore

10.0 out of 10, Exceptional, (74)
"Fantastic home for a large group. Everyone was comfortable in their spaces and appreciated the easy access to the Fenway area."
United States
Christeen R.
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Property grounds
NEW! Boston Condo Near MBTA, 3Mi to Fenway ! (U3)

Condo in 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)
TV, offices
Clean, Contemporary Escape | Near T

Vacation Home in Roxbury

9.4 out of 10, Exceptional, (19)
"Had a perfect stay! The place was wonderful and worked out for what we needed. Thank you!"
United States
Renee G.
Clean, Contemporary Escape | Near T
Exterior detail
Historic house renovated for modern convenience

Vacation Home in Brighton

9.8 out of 10, Exceptional, (134)
"His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
Historic house renovated for modern convenience
Fridge, microwave, oven, stovetop
Stylish, Comfortable Luxury | Near T

Condo in Roxbury

9.8 out of 10, Exceptional, (24)
"We had a great stay! Location was perfect and the beds were super cozy. 5 min walk to train station."
United States
Krystyna N.
Stylish, Comfortable Luxury | Near T
Fridge, microwave, oven, stovetop
Modern 2br with W/D in unit, Parking, central air

Condo in 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
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

Hampton Inn & Suites Boston Crosstown Center

Hampton Inn & Suites Boston Crosstown Center

10/10 Excellent
"Beautiful hotel parking was $25 friendly staff and 2 bar and restaurant on the first floor, pool was clean and up to date highly recommended "
Devdutt 1-night trip
Posted 1 day ago
Hampton Inn & Suites Boston Crosstown Center

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 $140 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?

Hidden Gem right in the city of Boston!: Visitors like this Ashland vacation home rental. It is located near skiing and offers a selection of games, air-conditioning, and free WiFi 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 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 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.