A river winding through a forest with autumn foliage.

Holiday Homes in Ashland

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Ashland holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

1. 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 NZ$493
includes taxes & fees
23 Aug - 24 Aug
Charming 3-bedroom house in delightful Ashland for your getaway

2. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is NZ$446
includes taxes & fees
23 Aug - 24 Aug
Game Room + Bar Lounge, 35 Min to Boston

3. Cambridge Designer Home / Harvard, MIT, Boston

Cambridge Designer Home / Harvard, MIT, Boston
Wellington-Harrington
The price is NZ$1,129
includes taxes & fees
13 Sept - 14 Sept
Cambridge Designer Home / Harvard, MIT, Boston

4. Entire Cambridge Home / Near Harvard, MIT & Boston

Entire Cambridge Home / Near Harvard, MIT & Boston
Ward Two
Entire Cambridge Home / Near Harvard, MIT & Boston
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

5. 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, (28 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is NZ$522
includes taxes & fees
23 Aug - 24 Aug
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.

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.4 out of 10, Exceptional, (13 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 NZ$742
includes taxes & fees
28 Aug - 29 Aug
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.

7. 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, (4 reviews)
"House was very well equipped and comfortable. Very close to nearby shopping. Felt like home without being home!"
United States
Matthew D.
The price is NZ$902
includes taxes & fees
23 Aug - 24 Aug
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
A modern living room with a blue sofa, a leather armchair, and a patterned rug.

8. Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool

Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
Framingham
10.0 out of 10, Exceptional, (6 reviews)
"Very nice"
United States
Tricia S.
The price is NZ$1,154
includes taxes & fees
14 Sept - 15 Sept
Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool

9. 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, (4 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 NZ$380
includes taxes & fees
20 Sept - 21 Sept
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.

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

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (36 reviews)
"Wonderful stay"
United States
Brent H.
The price is NZ$321
includes taxes & fees
24 Aug - 25 Aug
✨Private Studio w/ Loft Center Historic Carlisle✨
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
9.0 out of 10, Wonderful, (6 reviews)
"The apartment was perfect for our needs & the host communicated everything we needed without us needing to ask! Wonderful stay."
United States
Arwen D.
The price is NZ$342
includes taxes & fees
7 Sept - 8 Sept
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
A hallway with a dark grey door, a large ornate mirror, and a light wooden floor.

12. Harvard Charm / Near Boston + New build

Harvard Charm / Near Boston + New build
Ward Two
The price is NZ$819
includes taxes & fees
31 Aug - 1 Sept
Harvard Charm / Near Boston + New build
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

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

Modern Upper-Level Oasis, Minutes to Boston.
Norwood
9.8 out of 10, Exceptional, (7 reviews)
"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."
United States
Travis B.
The price is NZ$713
includes taxes & fees
7 Sept - 8 Sept
Modern Upper-Level Oasis, Minutes to Boston.
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

14. 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 NZ$432
includes taxes & fees
21 Aug - 22 Aug
Angel Sky Challenge
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a glass table and leather sofas.

15. 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
10.0 out of 10, Exceptional, (1 review)
"Was clean and easy to get into. Good amount of parking and easy to contact host with questions!"
United States
Julie C.
The price is NZ$775
includes taxes & fees
24 Aug - 25 Aug
Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with two chairs.

16. Bright & Cozy Woodland Home In Foxborough

Bright & Cozy Woodland Home In Foxborough
Foxborough
10.0 out of 10, Exceptional, (4 reviews)
"We loved the place, it’s clean and great location for going to concerts or Patriots games"
United States
Mark A.
The price is NZ$878
includes taxes & fees
24 Aug - 25 Aug
Bright & Cozy Woodland Home In Foxborough
A spacious living area with a dining table set for six, a sofa, and a kitchen in the background.

17. 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, (7 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 NZ$879
includes taxes & fees
25 Aug - 26 Aug
Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
A living room with a brown leather sofa, a black coffee table, and a television on a wooden stand.

18. 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, (20 reviews)
"Close walk to redline train. Walkable restaurants in area. Good location for using public transportation to get to downtown. Property very clean. Host responsive to inquiry’s."
United States
shelly H.
The price is NZ$1,071
includes taxes & fees
25 Aug - 26 Aug
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
A staircase with white balusters and blue handrails leading to a room with a bed and a painting on the wall.

19. 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
9.8 out of 10, Exceptional, (18 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 NZ$1,191
includes taxes & fees
25 Aug - 26 Aug
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
A modern kitchen with wooden cabinets, stainless steel appliances, and a tiled backsplash.

20. Elegant 5BR House Near Boston/ King Beds + 5 Free parking

Elegant 5BR House Near Boston/ King Beds + 5 Free parking
Dorchester
The price is NZ$1,178
includes taxes & fees
23 Aug - 24 Aug
Elegant 5BR House Near Boston/ King Beds + 5 Free parking
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

Hotel Commonwealth

Hotel Commonwealth

10/10 Excellent
"The staff was the best part. All were amazing. The gym needs improvement though. It’s small but still sizeable enough for some better equipment."
Roberto 3-night trip
Posted less than an hour ago
Hotel Commonwealth

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
153
Accommodation
342 Holiday Homes
Lowest Price
NZ$321
Highest Price
NZ$1,191