A river winding through a forest with autumn foliage.

Ashland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Ashland vacation rentals

Smart TV, fireplace, books, stereo

1. Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (10 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is AED 540
AED 845 total
includes taxes & fees
26 Oct - 27 Oct
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Coffee/tea maker, fridge, microwave, stovetop

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.4 out of 10, Exceptional, (16 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 AED 988
AED 1,592 total
includes taxes & fees
4 Oct - 5 Oct
totally remodeled house with fitness room, close to Boston and Worcester
Dining

3. Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
The price is AED 526
AED 772 total
includes taxes & fees
28 Sep - 29 Sep
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Interior

4. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (252 reviews)
"Wonderful!!"
United States
Huynh
The price is AED 334
AED 373 total
includes taxes & fees
1 Oct - 2 Oct
Residences at Solomon Pond
Interior

5. Spacious 3-bedroom apartment in lovely Millis with AC, WiFi

Spacious 3-bedroom apartment in lovely Millis with AC, WiFi
Millis
9.6 out of 10, Exceptional, (15 reviews)
"Great place to stay! "
United States
Jennifer B.
The price is AED 321
AED 1,000 total
includes taxes & fees
1 Oct - 2 Oct
Spacious 3-bedroom apartment in lovely Millis with AC, WiFi
Coffee/tea maker, fridge, microwave, oven

6. 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, (30 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is AED 853
AED 1,342 total
includes taxes & fees
4 Oct - 5 Oct
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
2 bedrooms, WiFi (free)

7. Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (37 reviews)
"Lovely and great location "
United States
Kimberlee K.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Terrace/patio

8. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,285 reviews)
"Great location, close to restaurants and stores. Beautiful rooms. Close enought to Boston without all the traffic. Close to Mass Pike."
United States
Mark
The price is AED 568
AED 635 total
includes taxes & fees
4 Oct - 5 Oct
Crescent Suites Hotel
Smart TV

9. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (54 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
2 bedrooms, iron/ironing board, WiFi

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

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.2 out of 10, Wonderful, (13 reviews)
"Good little spot, would reccommend."
Canada
Julien Alfred Joseph
The price is AED 496
AED 944 total
includes taxes & fees
27 Sep - 28 Sep
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Coffee/tea maker, fridge, microwave, oven

11. Sakura House: Spacious 4BR w/ Gym & Premium Design

Sakura House: Spacious 4BR w/ Gym & Premium Design
Northborough
10.0 out of 10, Exceptional, (14 reviews)
"Very comfortable stay. Highly recommend it."
United States
Susmitha R.
Sakura House: Spacious 4BR w/ Gym & Premium Design
Property grounds

12. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (70 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
The price is AED 507
AED 833 total
includes taxes & fees
30 Sep - 1 Oct
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
TV

13. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is AED 551
AED 1,114 total
includes taxes & fees
28 Sep - 29 Sep
Large 3BD 1st Floor Apartment Minutes from 290
Coffee/tea maker, fridge, microwave, oven

14. 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, (31 reviews)
"Everything was clean and welcoming. Kitchen had everything you need to cook, make coffee, etc. charming and comfortable "
United States
Lindsey D.
The price is AED 437
AED 808 total
includes taxes & fees
27 Sep - 28 Sep
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Exterior

15. Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.6 out of 10, Exceptional, (31 reviews)
"Beds were comfortable, location was convenient for our needs, thankful for the shoveling and clearing of snow in the morning! "
United States
Stephanie G.
The price is AED 657
AED 816 total
includes taxes & fees
27 Sep - 28 Sep
Charming 2-bedroom apartment with WiFi, AC in superb Canton
Exterior

16. ✨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 AED 364
AED 656 total
includes taxes & fees
5 Oct - 6 Oct
✨Private Studio w/ Loft Center Historic Carlisle✨
Dining

17. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
The price is AED 788
AED 924 total
includes taxes & fees
5 Oct - 6 Oct
Zen Inspired Retreat with Private Forest Trails
Smart TV

18. NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (53 reviews)
"That was the most comfortable bed I have slept in away from home!"
United States
Kimberly M.
The price is AED 455
AED 796 total
includes taxes & fees
25 Oct - 26 Oct
NEW Modern Apartment Near Boston & Harvard Square.
Smart TV, books

19. Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76

Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76
Dorchester
9.8 out of 10, Exceptional, (21 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 AED 587
AED 1,490 total
includes taxes & fees
29 Sep - 30 Sep
Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76
Outdoor dining

20. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (91 reviews)
"Honestly, the Boiler Room is even bigger than it looks in the pictures and is so perfectly curated! We LOVED our stay and if I ever get the opportunity to come back to Boaton, I will be staying here!"
United States
Katie C.
The price is AED 426
AED 1,208 total
includes taxes & fees
5 Oct - 6 Oct
🎖The Boiler Room - Close to Subway & Downtown🎖
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Hotel Commonwealth

Hotel Commonwealth

10/10 Excellent
"I've been to Boston six times. This hotel was the nicest, best located I've been in. One minute walk to the Kenmore Green Line subway, numerous low end and high end restaurants close by, close enough to Newbury Street to walk and--wait! There is something else....Oh, yeah!! Five minutes from Fenway Park and all the cool spots that happen before, during and after games. If this place appears to be a bit more expensive that the Hampton Inn, upgrade and make the reservation at the Commonwealth. You'll be glad you did!"
Kenneth 3-night trip
Posted 1 hour ago
Hotel Commonwealth

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?

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking: You might want to consider this vacation home rental near Ashland, which has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Ashland?

Expedia has 3 vacation rentals for your stay in Ashland.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Jordan's Furniture, 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.