Holiday Homes in Holliston

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Holliston holiday homes

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 €178
includes taxes & fees
9 Jun - 10 Jun
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Smart TV

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.6 out of 10, Exceptional, (47 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is €248
includes taxes & fees
3 Jun - 4 Jun
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Bathroom

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 €250
includes taxes & fees
8 Jun - 9 Jun
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Interior

Lorenzo Inn

Lorenzo Inn
Dorchester
10.0 out of 10, Exceptional, (1 review)
The price is €341
includes taxes & fees
9 Jun - 10 Jun
Lorenzo Inn
Shower, hair dryer, towels, soap

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 €186
includes taxes & fees
3 Jul - 4 Jul
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
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, (15 reviews)
"Overall, comfortable and well located. Host was quick to respond with any questions we had. "
United States
AJ V.
The price is €382
includes taxes & fees
8 Jun - 9 Jun
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
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
9.0 out of 10, Wonderful, (10 reviews)
"Property was as described. It was clean and owner was very responsive. Could walk to great coffee shop. "
United States
michelle s.
The price is €280
includes taxes & fees
7 Jun - 8 Jun
totally remodeled house with fitness room, close to Boston and Worcester
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 €254
includes taxes & fees
10 Jun - 11 Jun
Charming 3-bedroom house in delightful Ashland for your getaway
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 €226
includes taxes & fees
3 Jun - 4 Jun
Angel Sky Challenge
Smart TV, fireplace, books

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, (22 reviews)
"Clean home, comfortable beds, host very responsive."
United States
Richard M.
The price is €264
includes taxes & fees
10 Jun - 11 Jun
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Interior

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

Exclusive Summer Offer · Cozy 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
Dorchester
The price is €339
includes taxes & fees
4 Jun - 5 Jun
Exclusive Summer Offer · Cozy 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"10/10 great place to stay"
United States
Tyler B.
The price is €430
includes taxes & fees
10 Jun - 11 Jun
Spacious 4-bedroom with four and half bathrooms
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, (1 review)
"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 €359
includes taxes & fees
7 Jun - 8 Jun
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Private kitchen

Spacious 5BR Executive Retreat - 10 Min to Boston

Spacious 5BR Executive Retreat - 10 Min to Boston
Milton
Spacious 5BR Executive Retreat - 10 Min to Boston
Smart TV

Centrally located in the heart of Boston near T

Centrally located in the heart of Boston near T
Dorchester
9.0 out of 10, Wonderful, (22 reviews)
"Excellent stay! "
United States
Melissa R.
The price is €425
includes taxes & fees
3 Jun - 4 Jun
Centrally located in the heart of Boston near T
Fridge, microwave, oven, stovetop

Upper-Level Oasis – Ideal for 2026 World Cup 2026 visitors

Upper-Level Oasis – Ideal for 2026 World Cup 2026 visitors
Norwood
9.6 out of 10, Exceptional, (4 reviews)
"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."
United States
Travis B.
The price is €359
includes taxes & fees
8 Jun - 9 Jun
Upper-Level Oasis – Ideal for 2026 World Cup 2026 visitors
Fridge, microwave, oven, stovetop

Spacious Home ~Families & Groups~ Parking~Backyard

Spacious Home ~Families & Groups~ Parking~Backyard
Roxbury
The price is €754
includes taxes & fees
8 Jun - 9 Jun
Spacious Home ~Families & Groups~ Parking~Backyard
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.
Cozy house close to Brandeis, Bentley, Moody St
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, (24 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 €691
includes taxes & fees
10 Jun - 11 Jun
Funky and cozy home ! A little bit of everything for everyone.
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, (12 reviews)
"We loved this home. It was clean, well equipped and very well located for our family of 8 to visit Boston. Had a great time and loved the house. "
United States
Arlene P.
The price is €485
includes taxes & fees
3 Jun - 4 Jun
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
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 Holliston Hotel Reviews

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

6/10 Okay
"Entiendo que esta sobreprecio. No vimos que mas que cafe y una fruta. Fuimos temprano y mas tarde y fue igual. Esta limpio, la cama bien, y el servicio de recepcion es muy bueno y la atencion del personal tambien."
Juan 3-night trip
Posted 1 hour ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Holliston

Holliston Holiday Homes information

Number of reviews
19,667
Accommodation
335 Holiday Homes
Lowest Price
€75
Highest Price
€249