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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Ashland holiday homes

A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

1. 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
9.6 out of 10, Exceptional, (34 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is €358
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

2. 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, (17 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 €356
includes taxes & fees
28 Oct - 29 Oct
totally remodeled house with fitness room, close to Boston and Worcester
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

3. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"The house was nice. The beds were very comfortable. The house was close to everything. Check-in and check-out process was easy."
United States
Christina S.
The price is €489
includes taxes & fees
28 Oct - 29 Oct
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
A spacious living room with wooden beams, a sliding glass door to a patio, and a cozy seating area with a sofa and chairs.

4. Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
Framingham
10.0 out of 10, Exceptional, (3 reviews)
"Clean, pet friendly"
United States
Rebecca M.
Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
A spacious living area with a large sectional sofa, a glass coffee table, and a view of the outdoors through large windows.

5. 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, (7 reviews)
"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 €245
includes taxes & fees
1 Nov - 2 Nov
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
A two-story house with a front porch and a garden with purple flowers.

6. ✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.2 out of 10, Wonderful, (37 reviews)
"Wonderful stay"
United States
Brent H.
The price is €154
includes taxes & fees
25 Oct - 26 Oct
✨Private Studio w/ Loft Center Historic Carlisle✨
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

7. Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
The price is €371
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A two-story house with a central entrance, a brick foundation, and a large front yard.

8. 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 €236
includes taxes & fees
23 Oct - 24 Oct
Angel Sky Challenge
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

9. Modern Upper-Level Oasis, Minutes to Boston.

Modern Upper-Level Oasis, Minutes to Boston.
Norwood
9.8 out of 10, Exceptional, (9 reviews)
"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."
United States
Travis B.
The price is €400
includes taxes & fees
25 Oct - 26 Oct
Modern Upper-Level Oasis, Minutes to Boston.
A covered deck with outdoor furniture, a grill, and a sliding glass door leading to a bedroom.

10. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is €253
includes taxes & fees
25 Oct - 26 Oct
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

11. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.4 out of 10, Exceptional, (8 reviews)
"Amazing place and great host!"
United States
Harmoni C.
The price is €189
includes taxes & fees
9 Nov - 10 Nov
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
A modern office space with a desk, chair, and a flat-screen monitor.

12. Newly Renovated 3BR Private Home in Newton

Newly Renovated 3BR Private Home in Newton
Newton Center
The price is €360
includes taxes & fees
5 Nov - 6 Nov
Newly Renovated 3BR Private Home in Newton
A living room with a glass coffee table, two sofas, a dining table with chairs, and lamps.

13. 4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking

4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
Norwood
10.0 out of 10, Exceptional, (3 reviews)
"Not only was Joseph, our host, very accommodating, but the house was amazing! Each bed was comfortable, and each room had a TV. The life size connect 4, the video games, and the fact that every room had AC was an exciting surprise. I would definitely recommend staying here."
United States
Chris B.
The price is €650
includes taxes & fees
28 Oct - 29 Oct
4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
A kitchen with white cabinets, a black faucet, and a dish rack with utensils.

14. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is €493
includes taxes & fees
26 Oct - 27 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A modern kitchen with white cabinets, stainless steel appliances, and wooden shelves. There is a dining area with wicker chairs and a wooden table.

15. Budget-Friendly Basement 2BR Retreat

Budget-Friendly Basement 2BR Retreat
Roslindale
10.0 out of 10, Exceptional, (21 reviews)
"What a beautiful hide-a-way! Truly a diamond in the rough. "
United States
Twanna M.
Budget-Friendly Basement 2BR Retreat
A stainless steel range hood with a digital display and a warning label.

16. Designer Condo in Jamaica Plain | Steps to Forest Hills

Designer Condo in Jamaica Plain | Steps to Forest Hills
Roslindale
The price is €649
includes taxes & fees
28 Oct - 29 Oct
Designer Condo in Jamaica Plain | Steps to Forest Hills
A modern kitchen with a large island, white cabinets, and a dining area with a wooden table and chairs.

17. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is €626
includes taxes & fees
26 Oct - 27 Oct
Entire home in Sterling, Massachusetts, United States
A spacious room with a wooden floor, a white door, and a large window with a view of a staircase.

18. The Harvard Room conveniently near BC & Harvard

The Harvard Room conveniently near BC & Harvard
Brighton
9.0 out of 10, Wonderful, (40 reviews)
"The stay here was perfect for my wife and me. It is close ( 0.5 miles) to the purple line, even closer (.2 miles) to a bus stop, and close to restaurants and a brewery (Notch).Note: Big Daddy's Pizza is very close.2 miles) and was superb!"
United States
Michael D.
The price is €320
includes taxes & fees
26 Oct - 27 Oct
The Harvard Room conveniently near BC & Harvard
A kitchen counter with a coffee maker, a kettle, a coffee machine, two bottles of Torani syrup, a pack of Yogi tea, a wooden board with snacks, and a fruit platter.

19. Cambridge Designer Home / Harvard, MIT, Boston

Cambridge Designer Home / Harvard, MIT, Boston
Wellington-Harrington
The price is €403
includes taxes & fees
15 Nov - 16 Nov
Cambridge Designer Home / Harvard, MIT, Boston
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

20. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
The price is €447
includes taxes & fees
25 Oct - 26 Oct
Spacious 4-bedroom with four and half bathrooms
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

8/10 Good
".."
David 1-night trip
Posted 1 hour ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
128
Accommodation
295 Holiday Homes
Lowest Price
€154
Highest Price
€650