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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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Ashland vacation rentals

Private kitchen

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 AED 552
AED 1,131 total
includes taxes & fees
24 Jun - 25 Jun
Charming 3-bedroom house in delightful Ashland for your getaway
Premium Apartment | Living area | 24-inch Smart TV with digital channels

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 AED 588
AED 1,140 total
includes taxes & fees
30 Jun - 1 Jul
The Chester Hotel
Studio | Iron/ironing board, free WiFi

The Concord Hotel

The Concord Hotel
2.0 star property
South End
The price is AED 640
AED 1,200 total
includes taxes & fees
30 Jun - 1 Jul
The Concord Hotel
Exterior

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (3 reviews)
"It was a great stay!"
United States
Adina S.
The price is AED 301
AED 929 total
includes taxes & fees
6 Jul - 7 Jul
Light-filled Studio | Back Bay
TV

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is AED 367
AED 1,113 total
includes taxes & fees
24 Jun - 25 Jun
Beautiful 1BR near Fenway Park + Kenmore!
Outdoor dining

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (82 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 AED 437
AED 1,372 total
includes taxes & fees
14 Jul - 15 Jul
🎖The Boiler Room - Close to Subway & Downtown🎖
TV

Cozy Studio in the South End

Cozy Studio in the South End
Back Bay
The price is AED 382
AED 1,051 total
includes taxes & fees
1 Jul - 2 Jul
Cozy Studio in the South End
TV

Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2

Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2
Dorchester
10.0 out of 10, Exceptional, (18 reviews)
"Very nice property, parking is safe, owner give clear checkin and checkout instructions. Very good."
United States
Kevin
The price is AED 624
AED 1,448 total
includes taxes & fees
24 Jun - 25 Jun
Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2
Exterior

Artisan Studio with Exposed Brick

Artisan Studio with Exposed Brick
Back Bay
8.0 out of 10, Very Good, (1 review)
"Great space, great location. Excellent communication with host. Bathroom was a bit small and outdated. Worked for a short stay."
United States
Jim P.
The price is AED 360
AED 1,014 total
includes taxes & fees
6 Jul - 7 Jul
Artisan Studio with Exposed Brick
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (4 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 AED 743
AED 1,213 total
includes taxes & fees
24 Jun - 25 Jun
Symple Live
TV

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
The price is AED 430
AED 1,203 total
includes taxes & fees
30 Jun - 1 Jul
Charming 1 Bedroom | Newbury Street
Exterior

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 AED 529
AED 1,037 total
includes taxes & fees
30 Jun - 1 Jul
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Private kitchen

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 AED 465
AED 759 total
includes taxes & fees
16 Jul - 17 Jul
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Exterior

Tranquil South End Studio

Tranquil South End Studio
Back Bay
The price is AED 466
AED 1,175 total
includes taxes & fees
1 Jul - 2 Jul
Tranquil South End Studio
Desk, iron/ironing board, WiFi, bed sheets

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 AED 830
AED 1,649 total
includes taxes & fees
5 Jul - 6 Jul
The Chester: Urban Chic Stay In South End
Exterior

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, (175 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is AED 704
AED 809 total
includes taxes & fees
24 Jun - 25 Jun
Maverick Suites at 245 Newbury St
Exterior

Compact Back Bay Studio

Compact Back Bay Studio
Back Bay
The price is AED 602
AED 1,378 total
includes taxes & fees
24 Jun - 25 Jun
Compact Back Bay Studio
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (156 reviews)
"The property is clean and for the money, is a win for the visitor. "
United States
Ramon S
The price is AED 605
AED 695 total
includes taxes & fees
30 Jun - 1 Jul
Maverick Suites at 400 Columbus Ave
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (376 reviews)
"Great stay. "
United States
Anna
The price is AED 479
AED 910 total
includes taxes & fees
28 Jun - 29 Jun
Maverick Suites at 28 Fenway
TV

Stunning 1BR | Steps to Fenway!

Stunning 1BR | Steps to Fenway!
Fenway–Kenmore
10.0 out of 10, Exceptional, (1 review)
"Nice place, good location. Would definitely stay again!"
United States
Amy K.
The price is AED 514
AED 1,322 total
includes taxes & fees
29 Jun - 30 Jun
Stunning 1BR | Steps to Fenway!
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

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"Our room was clean and bigger than the ones in NY and DC and for less. We didn't have much contact with the staff as we were always on the go. We had a clean room and fresh towels. We walked everywhere we wanted and used Uber twice. Great location, maybe not the best for where we wanted to go, but that had zero impact on anything! I think the closer to the Center was a lot more expensive. I would 100% stay here again. Clean and safe, slept well!"
John 2-night trip
Posted less than an hour ago
The Midtown Hotel MOD Collection by Sonesta

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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?

Charming 3-bedroom house in delightful Ashland for your getaway: Visitors give good reviews to this Ashland vacation home rental, which comes with laundry facilities so you can feel at home during your trip.

How many vacation rentals are there in Ashland?

Expedia has 3 vacation rentals for your stay in Ashland.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Medfield Meadow Lots, 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 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.