Search Vacation Homes in Boston Highland Station

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sep - 7 Sep

Vacation Homes in Boston Highland Station

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Smart TV, video games, computer monitors, printers

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

9.8 out of 10, Exceptional, (60)
"The property is a great place for a family to stay. Plenty of room, well stocked kitchen, a great location in Boston. Highly recommend! "
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Terrific vacation house only 4.5 miles away from downtown Boston
Outdoor dining

Terrific vacation house only 4.5 miles away from downtown Boston

10.0 out of 10, Exceptional, (42)
"Our host went out of his way to help us in every way Great location for all conveniences."
The price is AED 1,488
AED 2,892 total
includes taxes & fees
17 Jul - 18 Jul
Terrific vacation house only 4.5 miles away from downtown Boston
Stylish Boston Getaway Near Arboretum & T Station!
Exterior

Stylish Boston Getaway Near Arboretum & T Station!

Stylish Boston Getaway Near Arboretum & T Station!
Budget-Friendly Basement 2BR Retreat
Fridge, stovetop

Budget-Friendly Basement 2BR Retreat

10.0 out of 10, Exceptional, (18)
"This property was clean and safe and exactly what we needed! We will definitely be back! Thank you Hitesh! "
Budget-Friendly Basement 2BR Retreat
The Arbor Retreat
Property grounds

The Arbor Retreat

10.0 out of 10, Exceptional, (5)
"My boyfriend and I stayed here for two nights. We loved the property and ease of the check-in process! The property was clean and cozy, with tea and coffee provided (as well as other utensils if you wished to cook). The owners left a "guestbook guide" that had great recommendations for restaurants and things to do around Jamaica Plain. This property is about 5-10 minutes from hot spots in downtown Boston (e.g Fenway). We highly recommend this location and would love to stay again in the future!"
The Arbor Retreat
This Apartment is an great aerie in Boston
Fridge, microwave, oven, stovetop

This Apartment is an great aerie in Boston

10.0 out of 10, Exceptional, (1)
"Everything about this place was awesome! Easy access to stores, trains to the city, and house was awesome!"
This Apartment is an great aerie in Boston
Spacious Single Family House - Great Privacy, 19' train ride to Back Bay Station
Outdoor dining

Spacious Single Family House - Great Privacy, 19' train ride to Back Bay Station

10.0 out of 10, Exceptional, (5)
"Thank you for a very pleasant stay in your spacious and comfortable home."
Spacious Single Family House - Great Privacy, 19' train ride to Back Bay Station
Renovated 2nd-Floor Home |
Fridge, stovetop

Renovated 2nd-Floor Home |

9.6 out of 10, Exceptional, (31)
"Nice location, place as described. Very clean. "
Renovated 2nd-Floor Home |
1918 Family Home near Boston
Fridge, microwave, oven, stovetop

1918 Family Home near Boston

10.0 out of 10, Exceptional, (33)
"Our family celebrated Christmas at the house and it was perfect ! Great hosts! Cozy home. "
1918 Family Home near Boston
“Arboretum Retreat” city of Boston
3 bedrooms, WiFi

“Arboretum Retreat” city of Boston

10.0 out of 10, Exceptional, (4)
"Great location in Roslindale..very helpful host."
“Arboretum Retreat” city of Boston
Comfortable 4-bedroom house 20 minute drive to the Boston Commons.
Exterior

Comfortable 4-bedroom house 20 minute drive to the Boston Commons.

Comfortable 4-bedroom house 20 minute drive to the Boston Commons.
Charming Boston Townhouse
Outdoor dining

Charming Boston Townhouse

Charming Boston Townhouse
Beautiful 2BR apartment in historic house. Walkable neighborhood!
Living area

Beautiful 2BR apartment in historic house. Walkable neighborhood!

Beautiful 2BR apartment in historic house. Walkable neighborhood!
Experience the history of Boston in the most sought after neighborhood.
Exterior

Experience the history of Boston in the most sought after neighborhood.

Experience the history of Boston in the most sought after neighborhood.
Roslindale 3 bedroom 2000 sq ft home with free parking
Smart TV

Roslindale 3 bedroom 2000 sq ft home with free parking

Roslindale 3 bedroom 2000 sq ft home with free parking
Cheerful, family friendly 2 bedroom 3 miles from US Open!
Exterior

Cheerful, family friendly 2 bedroom 3 miles from US Open!

Cheerful, family friendly 2 bedroom 3 miles from US Open!
Single room, access to all household amenities, steps from commuter rail
Living area

Single room, access to all household amenities, steps from commuter rail

Single room, access to all household amenities, steps from commuter rail
One mile from US OPEN Country Club
3 bedrooms, WiFi

One mile from US OPEN Country Club

One mile from US OPEN Country Club
Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village
1 bedroom, WiFi

Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village

Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free