Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Ashland vacation rentals

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, (28 reviews)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is ￥27,899
￥60,393 total
includes taxes & fees
Mar 17 - Mar 18
The Chester Hotel
Oven, stovetop, dishwasher, coffee/tea maker

South End Serene Studio

South End Serene Studio
Back Bay
The price is ￥24,958
￥56,440 total
includes taxes & fees
Mar 17 - Mar 18
South End Serene Studio
Exterior

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very Good, (9 reviews)
"This location is so convenient to BU! Loved how easy check-in was!"
United States
Laura B.
The price is ￥15,738
￥35,568 total
includes taxes & fees
Mar 19 - Mar 20
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Exterior

Unique South End Studio

Unique South End Studio
Back Bay
Unique South End Studio
Desk, iron/ironing board, WiFi, bed sheets

The only 4 Bedroom Apartment w/ Roofdeck in Boston! 8min from Fenway Park, close to universities!

The only 4 Bedroom Apartment w/ Roofdeck in Boston! 8min from Fenway Park, close to universities!
Fenway–Kenmore
The price is ￥20,284
￥80,383 total
includes taxes & fees
Mar 16 - Mar 17
The only 4 Bedroom Apartment w/ Roofdeck in Boston! 8min from Fenway Park, close to universities!
Fridge, microwave, oven, stovetop

80-2 4BR Boston - Bright Family Stay near PJP II Park

80-2 4BR Boston - Bright Family Stay near PJP II Park
Dorchester
9.4 out of 10, Exceptional, (21 reviews)
"The host was always prompt in answering my questions and was able to accommodate my special requests. I would come back and stay here anytime. "
United States
Kelly D.
The price is ￥29,979
￥68,458 total
includes taxes & fees
Mar 18 - Mar 19
80-2 4BR Boston - Bright Family Stay near PJP II Park
Exterior detail

Save 30%, Pet-Friendly Boston Apartment, Free Parking, Near Red Line - 82

Save 30%, Pet-Friendly Boston Apartment, Free Parking, Near Red Line - 82
Dorchester
9.4 out of 10, Exceptional, (32 reviews)
"Very comfortable, lots of room, clean, well appointed.Great location. Appreciated off street parking."
United States
Sandra M.
The price is ￥25,677
￥62,057 total
includes taxes & fees
Mar 15 - Mar 16
Save 30%, Pet-Friendly Boston Apartment, Free Parking, Near Red Line - 82
Exterior

Lovely South End Studio

Lovely South End Studio
Back Bay
The price is ￥15,261
￥39,811 total
includes taxes & fees
Mar 22 - Mar 23
Lovely South End Studio
Exterior

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (7 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
The price is ￥19,394
￥47,368 total
includes taxes & fees
Mar 16 - Mar 17
Stylish Back Bay Retreat, Steps from Prudential
Living area

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.2 out of 10, Very Good, (35 reviews)
"Great place to stay! We loved our time there!"
United States
Melody
The price is ￥29,892
￥53,580 total
includes taxes & fees
Apr 7 - Apr 8
On River/Harvard Sq. two blocks
Fridge, microwave, oven, stovetop

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, (22 reviews)
"We had a fabulous time! It was nice to be able to travel with the dogs and having the fenced yard made it great for the dogs. We were able to visit all our relatives w/o displacing anyone, like before.We will be coming back!"
United States
VERNE W.
The price is ￥17,328
￥32,621 total
includes taxes & fees
Mar 15 - Mar 16
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
TV

558/2 - 3BR Boston - Modern Nest near Franklin Park

558/2 - 3BR Boston - Modern Nest near Franklin Park
Dorchester
10.0 out of 10, Exceptional, (16 reviews)
"Kitchen, bedrooms, and bathrooms were very well equipped and wonderfully clean. Give of us stayed there and it was very comfortable and welcoming. We would stay here again. "
United States
Robert B.
The price is ￥26,887
￥60,360 total
includes taxes & fees
Mar 18 - Mar 19
558/2 - 3BR Boston - Modern Nest near Franklin Park
2 bedrooms, iron/ironing board, WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.0 out of 10, Wonderful, (9 reviews)
"Very easy and accommodating stay right outside of the city. Would recommend for a stay. "
United States
Nolan B.
The price is ￥21,352
￥42,400 total
includes taxes & fees
Mar 23 - Mar 24
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
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, (337 reviews)
"Good place"
United States
Elijah
The price is ￥17,025
￥35,103 total
includes taxes & fees
Mar 23 - Mar 24
Maverick Suites at 28 Fenway
Fridge, microwave, oven, stovetop

60-3 3BR Boston - Sleek Apartment near Franklin Park

60-3 3BR Boston - Sleek Apartment near Franklin Park
Mattapan
9.6 out of 10, Exceptional, (25 reviews)
"Enjoyed our stay"
United States
Sybal C.
The price is ￥25,140
￥57,259 total
includes taxes & fees
Mar 15 - Mar 16
60-3 3BR Boston - Sleek Apartment near Franklin Park
TV

Wonderful Fenway 3br/2ba | Steps from Fenway Park!

Wonderful Fenway 3br/2ba | Steps from Fenway Park!
Fenway–Kenmore
The price is ￥22,838
￥69,062 total
includes taxes & fees
Mar 18 - Mar 19
Wonderful Fenway 3br/2ba | Steps from Fenway Park!
TV, offices

The Chester: Modern Luxury, Historic Charm

The Chester: Modern Luxury, Historic Charm
South End
9.0 out of 10, Wonderful, (2 reviews)
"Easy check in. Clean space. Cute decor and comfortable. Husband and I enjoyed the location. "
United States
Morgan Z.
The price is ￥27,836
￥60,632 total
includes taxes & fees
Mar 18 - Mar 19
The Chester: Modern Luxury, Historic Charm
TV

Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking

Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
Ward Two
9.8 out of 10, Exceptional, (12 reviews)
"Nice visit"
United States
Nate P.
The price is ￥20,974
￥56,288 total
includes taxes & fees
Mar 18 - Mar 19
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
2 bedrooms, WiFi, bed sheets

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, (30 reviews)
"Perfect location for Head of the Charles Regatta!"
United States
Kristy R.
The price is ￥18,362
￥39,119 total
includes taxes & fees
Mar 15 - Mar 16
Great Apartment on River/ Harvard Square two blocks
Interior

14/1 - 3BR Milton - Cozy Apt near Blue Hills Museum

14/1 - 3BR Milton - Cozy Apt near Blue Hills Museum
Milton
9.4 out of 10, Exceptional, (11 reviews)
"Just as lovely in person as in the pictures! Host was quick to respond to questions and very proactive with check in procedure. Wish we could have stayed longer!"
United States
Johnna K.
The price is ￥28,511
￥55,676 total
includes taxes & fees
Mar 22 - Mar 23
14/1 - 3BR Milton - Cozy Apt near Blue Hills Museum
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

Arcadian Hotel

Arcadian Hotel

4/10 Poor
"Bad breakfast. This place is more like college dorm."
Balaji 4-night trip
Posted 5 hours ago
Arcadian Hotel

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 | Near T: Visitors like this Ashland vacation home rental. It offers a patio, a garden, and air-conditioning 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 Fun and Games Family Entertainment Center, 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.