Photo by Swetha Srinivasan

Search Vacation Homes in Ashland

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 243 Vacation Homes in Ashland with updated reviews, rates, and availability.

Charming home with deck- walkable to transit, shops & restaurants

Charming home with deck- walkable to transit, shops & restaurants

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

10.0 out of 10, Exceptional, (56)
"Really enjoyed the house. Great location, easy checking in. They even had a decorated Christmas tree for us."
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T

Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

8.8 out of 10, Excellent, (20)
"Excellent property; easy to work with owners."
The price is AED 915
AED 1,656 total
includes taxes & fees
16 Mar - 17 Mar
Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (17)
"We had a wonderful stay. The apartment was exactly as advertised. It’s very clean and in a cute borough with some great restaurants and shops and any other convenience you might need. The apartment has a large kitchen that’s great for cooking your own meals if you wish to do so. Check in was completely seamless even though we were arriving late at night. "
The price is AED 477
AED 1,448 total
includes taxes & fees
24 Mar - 25 Mar
Hidden Gem right in the city of Boston!

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (44)
"We had a pleasant stay. The house is cozy, clean and comfortable. It is in a convenient location with several restaurants in walking distance as well as a supermarket. The neighborhood is quiet with little traffic coming through. Victor the host was responsive and answered any questions we had. Would recommend without hesitation."
Boston's Best Vacation Home

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

8.4 out of 10, Very Good, (7)
"Big house with a good living room kitchen space. Quite neighborhood. "
The price is AED 992
AED 1,850 total
includes taxes & fees
16 Mar - 17 Mar
Beautiful two-story home close to downtown worcester 5beds-4bedroom

Cozy 2-Floor Apartment with Garage Access

9.6 out of 10, Exceptional, (19)
"The unit is immaculately clean and comfortable. The host is incredibly responsive. I had a sudden and urgent need for her help. She responded to me within a few minutes and all was resolved. The unit is a short distance to WPI. Thank you."
Cozy 2-Floor Apartment with Garage Access

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"This is a really great apartment in a very convenient location, Cherie was a very attentive host and really we couldn’t have asked for better accommodation for our needs as a family. Thank you."
The price is AED 852
AED 1,674 total
includes taxes & fees
19 Mar - 20 Mar
Funky and cozy home ! A little bit of everything for everyone.

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (13)
"We had a wonderful time. The home was perfect for our stay and we will stay again to enjoy the water."
Worcester Home on Indian Lake w/ Shared Boat Dock!

76-1 - Boston Cozy Apartment Near Ashmont Station

10.0 out of 10, Exceptional, (1)
"My friends and I recently stayed here, and we would highly recommend other people to stay here as well. Jenny was a great host and always super responsive when I had any question. She made sure my friends and I had everything we needed (which wasn't much because the house came with everything we needed). Overall, it was the perfect place for me and my friends, and I am glad we got to stay here! "
The price is AED 694
AED 1,638 total
includes taxes & fees
23 Mar - 24 Mar
76-1 - Boston Cozy Apartment Near Ashmont Station

Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly

10.0 out of 10, Exceptional, (48)
"Super clean, quiet, and easy place to stay. Bathroom is really fancy/cool. Owner is very easy to work with!"
The price is AED 1,102
AED 1,940 total
includes taxes & fees
6 Apr - 7 Apr
Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly

Charming 4-bedroom house with WiFi, AC in amazing Foxborough

10.0 out of 10, Exceptional, (2)
"Lovely stay"
The price is AED 1,836
AED 3,216 total
includes taxes & fees
16 Mar - 17 Mar
Charming 4-bedroom house with WiFi, AC in amazing Foxborough

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (8)
"I just wanna say that everything about the listing is on point. My cousins and I had a great snowboarding weekend at Mount Wachusett and this property was the perfect location for us. Both Spacious and Clean the property is near everything and just a 25 min drive to the slopes..Will definitely stay there again.. "
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Historic house renovated for modern convenience

9.8 out of 10, Exceptional, (118)
"Really great location and the right size for our group! We had a great time"
Historic house renovated for modern convenience

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

9.6 out of 10, Exceptional, (52)
"We truly enjoyed our stay. The house is adorable and located in a beautiful suburban neighbourhoid. It was an excellent home base from which to explore Boston. The host is extremely accommodating and is easily contacted.We would 100% recommend this place as long as you have your own car to get around the city."
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

Home Away from Home!

10.0 out of 10, Exceptional, (2)
"Thank you for our little stay-cation! The property was beautiful and was exactly as expected. Plenty of rooms and bathrooms. My only wish was for more mirrors for us all to do our make up. But we made it work. "
The price is AED 683
AED 1,442 total
includes taxes & fees
17 Mar - 18 Mar
Home Away from Home!

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

9.8 out of 10, Exceptional, (21)
"The apartment was very clean and cozy but if you are tall watch out for the low ceilings. Being in an old home it has some wonderful character! The bed was very comfortable as well and has a nice living room with TV. I would highly recommend this place to stay. The host is also very receptive and on top of everything, thank you Ebenezer."
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Norwood Luxe Suite- Pet friendly & Commuter friendly

10.0 out of 10, Exceptional, (8)
"Our crew have been up several times in the area for work and really enjoyed staying here. The house is lovely and is always clean and welcoming when they arrive for their stay. Susan is an excellent communicator and a wonderful host!"
Norwood Luxe Suite- Pet friendly & Commuter friendly

Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to Subway

10.0 out of 10, Exceptional, (1)
"We truly enjoyed our stay here. All the amenities, furniture, & decorations were so well thought out. After a long day of sightseeing in Boston it was so nice to come home to your house. We loved all the space we had and hope to come back again! Thank you!"
Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to Subway
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.
Don't see what you're looking for?
See all available properties in Ashland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Ashland

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (445)
"The Gentleman at the front desk was amazing assisted us with everything."
The price is AED 770
AED 893 total
includes taxes & fees
22 Mar - 23 Mar
Sonder 907 Main

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (168)
"quiet and clean"
The price is AED 353
AED 764 total
includes taxes & fees
24 Mar - 25 Mar
Maverick Suites at 28 Fenway

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (875)
"Very quaint, clean space with amazing access to the Boston area. Right between Newbury and Comm Ave, with lots to eat and enjoy."
The price is AED 778
AED 918 total
includes taxes & fees
30 Mar - 31 Mar
No. 284 powered by Sonder
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.