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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
17 July - 19 July
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Ashland holiday homes

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 AU$421
includes taxes & fees
6 July - 7 July
Charming 3-bedroom house in delightful Ashland for your getaway
Shower, hair dryer, towels, soap

2-bedroom townhome in Primary Cambridge location. Walking to MIT and Red line.

2-bedroom townhome in Primary Cambridge location. Walking to MIT and Red line.
Cambridgeport
The price is AU$650
includes taxes & fees
27 July - 28 July
2-bedroom townhome in Primary Cambridge location. Walking to MIT and Red line.
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 AU$297
includes taxes & fees
14 July - 15 July
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Interior

76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston

76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Dorchester
10.0 out of 10, Exceptional, (14 reviews)
"Our stay was excellent, the property was clean and spacious with everything we needed. The host was responsive and very helpful before and throughout the trip."
United States
Clark A.
The price is AU$813
includes taxes & fees
7 July - 8 July
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Exterior

✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (34 reviews)
"Wonderful stay"
United States
Brent H.
The price is AU$328
includes taxes & fees
14 July - 15 July
✨Private Studio w/ Loft Center Historic Carlisle✨
Smart TV, fireplace, books

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
10.0 out of 10, Exceptional, (1 review)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
United States
Eva O.
The price is AU$286
includes taxes & fees
16 July - 17 July
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Fridge, microwave, oven, stovetop

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.8 out of 10, Exceptional, (25 reviews)
"Clean home, comfortable beds, host very responsive."
United States
Richard M.
The price is AU$498
includes taxes & fees
3 Aug - 4 Aug
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Dining

Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17

Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
Randolph
10.0 out of 10, Exceptional, (6 reviews)
"It was a cozy and clean home with everything needed to accommodate your stay. My family and young nephews had a great time here and I’d recommend it to anyone looking to visit Boston"
United States
Nicholas P.
The price is AU$916
includes taxes & fees
14 July - 15 July
Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
Fridge, microwave, stovetop, coffee/tea maker

totally remodeled house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.2 out of 10, Wonderful, (11 reviews)
"Nicely located in neighbor with easy access to highways and walking distance to coffee shop this single home is perfect for being near Boston. Space is comfortable with all the comforts of home. "
United States
Karyn V.
The price is AU$502
includes taxes & fees
17 July - 18 July
totally remodeled house with fitness room, close to Boston and Worcester
Smart TV, books

76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Dorchester
9.6 out of 10, Exceptional, (16 reviews)
"Amazing location close to everything you are going to want to see in Boston, and great communication with the host."
United States
Shane M.
The price is AU$690
includes taxes & fees
28 July - 29 July
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Property grounds

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
Worcester
9.8 out of 10, Exceptional, (17 reviews)
"Great host! Easy to contact via text. Home was clean and perfect for my family!"
United States
Michael B.
The price is AU$647
includes taxes & fees
19 July - 20 July
Lakefront Cottage 2 Mi to Palladium in Worcester!
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is AU$547
includes taxes & fees
26 July - 27 July
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Interior

Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is AU$376
includes taxes & fees
6 July - 7 July
Angel Sky Challenge
Desk, iron/ironing board, travel cot, free WiFi

Harvard Charm / Near Boston + New build

Harvard Charm / Near Boston + New build
Wellington-Harrington
The price is AU$977
includes taxes & fees
13 July - 14 July
Harvard Charm / Near Boston + New build
Private kitchen

Bright & Cozy Woodland Home In Foxborough

Bright & Cozy Woodland Home In Foxborough
Foxborough
10.0 out of 10, Exceptional, (1 review)
"Great host hospitality"
United States
Elijah S.
The price is AU$609
includes taxes & fees
14 July - 15 July
Bright & Cozy Woodland Home In Foxborough
TV

Cozy house close to Brandeis, Bentley, Moody St

Cozy house close to Brandeis, Bentley, Moody St
South Side
9.2 out of 10, Wonderful, (7 reviews)
"We enjoy our stayed at the place.it’s nice and clean."
United States
Gabriel C.
The price is AU$724
includes taxes & fees
6 July - 7 July
Cozy house close to Brandeis, Bentley, Moody St
Fridge, microwave, oven, stovetop

Boston 5BR Retreat Sleeps 12 Free Parking Backyard

Boston 5BR Retreat Sleeps 12 Free Parking Backyard
Roxbury
The price is AU$702
includes taxes & fees
6 July - 7 July
Boston 5BR Retreat Sleeps 12 Free Parking Backyard
Exterior detail

Funky and cozy home ! A little bit of everything for everyone.

Funky and cozy home ! A little bit of everything for everyone.
Arlington
10.0 out of 10, Exceptional, (26 reviews)
"Fantastic home, very clean, great location, and wonderful communication with the host. Truly a 5 star stay!"
United States
Tim S.
The price is AU$1,016
includes taxes & fees
12 July - 13 July
Funky and cozy home ! A little bit of everything for everyone.
Interior

Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2

Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
Dorchester
The price is AU$830
includes taxes & fees
12 July - 13 July
Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
Fridge, microwave, oven, stovetop

3BR Upper-Level Oasis, Minutes to Boston Stadium, World Cup Ready

3BR Upper-Level Oasis, Minutes to Boston Stadium, World Cup Ready
Norwood
9.8 out of 10, Exceptional, (7 reviews)
"Nice location. Close to everything. Quiet neighborhood. House was very clean and ready for us. Communication with host was excellent."
United States
David S.
The price is AU$700
includes taxes & fees
20 July - 21 July
3BR Upper-Level Oasis, Minutes to Boston Stadium, World Cup Ready
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 Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

10/10 Excellent
"The hotel is well located and the rooms are clean and spacious"
Luis Pedro Del Valle 2-night trip
Posted less than an hour ago
The Colonnade Hotel Back Bay

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
175
Accommodation
323 Holiday Homes
Lowest Price
AU$286
Highest Price
AU$1,016