Ashland Reservoir aerial view with fall foliage in Ashland State Park in town of Ashland, Massachusetts MA, USA.

Ashland Vacation Rentals

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Our top choices for Ashland vacation 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 ¥24,373
¥50,152 total
includes taxes & fees
Jun 21 - Jun 22
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 ¥25,638
¥49,732 total
includes taxes & fees
Jun 30 - Jul 1
The Chester Hotel

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
8.0 out of 10, Very Good, (2 reviews)
"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 ¥27,719
¥47,518 total
includes taxes & fees
Jul 15 - Jul 16
Symple Live

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, (23 reviews)
"Friendly hosts"
United States
Jan
The price is ¥27,722
¥51,330 total
includes taxes & fees
Jun 19 - Jun 20
Free Parking at 1 Bed Basement Apt, Near BU & MIT

The Chester: Urban Chic Stay In South End

The Chester: Urban Chic Stay In South End
South End
10.0 out of 10, Exceptional, (1 review)
"We had a great stay in Boston and the Chester was perfect for our trip. First time in Boston so we did a lot of the usual things, but this location was great to easily connect with bus and train options as we decided not to rent a vehicle. Space was comfortable for group of three - lots of shops and restaurants in the area. We were touring a lot, so didn’t spend a lot of time in the unit, but it was very comfortable and would definitely come back again!"
United States
Chad T.
The price is ¥32,689
¥66,956 total
includes taxes & fees
Jul 1 - Jul 2
The Chester: Urban Chic Stay In South End

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 ¥35,573
¥66,285 total
includes taxes & fees
Jul 1 - Jul 2
Stylish Back Bay Retreat, Steps from Prudential

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Fenway–Kenmore
10.0 out of 10, Exceptional, (2 reviews)
"Great location with comfortable accommodations!! Easy access to great restaurants, Fenway, and the T. Host provided excellent communication and was extremely responsive. Highly recommend!"
United States
Andrea G.
The price is ¥30,926
¥71,686 total
includes taxes & fees
Jul 6 - Jul 7
Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway

Serene South End Studio

Serene South End Studio
Back Bay
10.0 out of 10, Exceptional, (1 review)
"Nice and clean room, close walking distance to Ma General hospital and also BU Hospital, and nice friendly staff. Would rent again!"
United States
Dylan S.
Serene South End Studio

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 ¥13,140
¥40,700 total
includes taxes & fees
Jul 6 - Jul 7
Light-filled Studio | Back Bay

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

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.4 out of 10, Exceptional, (19 reviews)
"Beds were comfortable, location was convenient for our needs, thankful for the shoveling and clearing of snow in the morning! "
United States
Stephanie G.
The price is ¥28,683
¥36,155 total
includes taxes & fees
Jun 17 - Jun 18
Charming 2-bedroom apartment with WiFi, AC in superb Canton

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very Good, (44 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is ¥30,285
¥54,100 total
includes taxes & fees
Jun 30 - Jul 1
On River/Harvard Sq. two blocks

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,219 reviews)
"Everything was comfortable."
United States
John
The price is ¥25,815
¥28,835 total
includes taxes & fees
Jul 5 - Jul 6
Crescent Suites Hotel

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, (37 reviews)
"Clean apartment. Close to Harvard Square. Stairs not user-friendly."
United States
Jeffrey
The price is ¥30,285
¥55,202 total
includes taxes & fees
Jun 30 - Jul 1
Great Apartment on River/ Harvard Square two blocks

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
The price is ¥19,069
¥52,899 total
includes taxes & fees
Jun 21 - Jun 22
Charming 1 Bedroom | Newbury Street

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (32 reviews)
"Lovely and great location "
United States
Kimberlee K.
The price is ¥27,257
¥49,598 total
includes taxes & fees
Jun 21 - Jun 22
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Blissful South End Studio

Blissful South End Studio
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is ¥24,837
¥57,675 total
includes taxes & fees
Jun 29 - Jun 30
Blissful South End Studio

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (213 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is ¥31,888
¥64,285 total
includes taxes & fees
Jun 30 - Jul 1
Charlesgate Suites

Compact Back Bay Studio

Compact Back Bay Studio
Back Bay
The price is ¥32,689
¥69,429 total
includes taxes & fees
Jun 24 - Jun 25
Compact Back Bay Studio

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (81 reviews)
"Host was amazing and responded right away with any questions or concerns we had! Beautiful place to stay!"
United States
Amy I.
The price is ¥23,876
¥65,022 total
includes taxes & fees
Jun 21 - Jun 22
🎖The Boiler Room - Close to Subway & Downtown🎖

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is ¥22,914
¥58,672 total
includes taxes & fees
Jun 21 - Jun 22
Beautiful 1BR near Fenway Park + Kenmore!
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Top Ashland Hotel Reviews

Find out more about Ashland

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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?

Clean contemporary escape: Visitors like this Ashland vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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 Apex Entertainment Center, or get outside and enjoy nature at Framingham Town Common. Other places in town to visit include Ashland State Park and Hopkinton 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.