Vacation Rentals in Highland Park, MA

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Highland Park, MA

Book a vacation rental in Highland Park that has the highest visitor rating. Here are 6 of the best vacation rentals in Highland Park.
*Fort Hill Inn *Sunny* Penthouse Duplex!! L@@K 3 bed, 2 bath, 1.5 miles Center
10

Excellent

·
Highland Park
·
3 br
·
Sleeps 6
·
Fireplace · Wifi · Dishwasher ·
From
$356/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Fireplace
Wifi
Dishwasher
Air Conditioning
Elevator
Hardwood Floor
Furnished
Oven
Other spaces
Kitchen
Price drop
Stylish Modern Home | near South End
10

Excellent

·
Highland Park
·
1 br
·
Sleeps 7
·
Wifi · Air Conditioning · Kitchen ·
From
$159/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Wifi
Air Conditioning
Furnished
Dishwasher
In Unit Laundry
Package Service
Oven
Other spaces
Kitchen
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
10

Excellent

·
Highland Park
·
4 br
·
Sleeps 8
·
Air Conditioning · Fireplace · Dishwasher ·
From
$518/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Air Conditioning
Fireplace
Dishwasher
Oven
In Unit Laundry
Elevator
Furnished
Hardwood Floor
Other spaces
Kitchen
Price drop
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
10

Excellent

·
Highland Park
·
1 br
·
Sleeps 4
·
Air Conditioning · In Unit Laundry · Wifi ·
From
$175/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
In Unit Laundry
Wifi
Furnished
Dishwasher
Fitness Center
Fireplace
Oven
Other spaces
Workspace, Kitchen
Price drop
SUNNY!! ***BOOK NOW!*** FABULOUS! ** UbEr Cool** Minutes to Center!
10

Excellent

·
Highland Park
·
3 br
·
Sleeps 8
·
Dishwasher · Wifi · Furnished ·
From
$350/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Dishwasher
Wifi
Furnished
Fitness Center
In Unit Laundry
Fireplace
Oven
Air Conditioning
Other spaces
Kitchen, Workspace
Price drop
**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!
10

Excellent

·
Highland Park
·
4 br
·
Sleeps 8
·
Fireplace · In Unit Laundry · Kitchen ·
From
$550/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Fireplace
In Unit Laundry
Hardwood Floor
Air Conditioning
Wifi
Furnished
Elevator
Other spaces
Kitchen

Our Recommended Vacation Rentals in Highland Park, MA

We analyzed vacation rentals in Highland Park from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Highland Park to help you find a deal for your next trip.
Price drop
Luxe Home | Near T Su

No rating

·
Highland Park
·
2 br
·
Sleeps 6
·
Oven · Balcony · Kitchen ·
From
$225/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Oven
In Unit Laundry
Air Conditioning
Wifi
Dishwasher
Furnished
Package Service
Other spaces
Balcony, Kitchen
Beautiful Two Bedroom Apartment.

No rating

·
Highland Park
·
2 br
·
Sleeps 3
·
Wifi · Oven · In Unit Laundry ·
From
$115/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Wifi
Oven
In Unit Laundry
Dishwasher
Furnished
Air Conditioning
Other spaces
Kitchen
Price drop
Expansive Luxury Triplex | near T

No rating

·
Highland Park
·
7 br
·
Sleeps 29
·
Furnished · Kitchen · Oven ·
From
$838/night
Check availability
Property
House · 7 Beds · 5 baths
Amenities
Furnished
Oven
Package Service
Central Heat
Wifi
Air Conditioning
In Unit Laundry
Other spaces
Kitchen
Price drop
Charming Luxury Duplex | near T

No rating

·
Highland Park
·
3 br
·
Sleeps 14
·
In Unit Laundry · Package Service · Furnished ·
From
$283/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
In Unit Laundry
Package Service
Furnished
Air Conditioning
Oven
Wifi
Dishwasher
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Highland Park, MA

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Highland Park starting at $85. Use the price filter at the top of the page to search for more specific prices.
4BD 1 and half BTH Comfy Newly Renovated Apt
6.9

Good

·
Highland Park
·
4 br
·
Sleeps 8
·
Wifi · Kitchen · Workspace ·
From
$85/night
Check availability
Property
Apartment · 4 Beds · 1 bath
Amenities
Wifi
Furnished
Smoking Allowed
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Other spaces
Kitchen, Workspace
Price drop
Charming 2 level apartment

No rating

·
Highland Park
·
1 br
·
Sleeps 1
·
Air Conditioning · Wifi · Oven ·
From
$115/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Wifi
Oven
Furnished
In Unit Laundry
Dishwasher
Other spaces
Kitchen
Furnished 2 BED Near Hospitals top of Ft Hill Park

No rating

·
Highland Park
·
2 br
·
Microwave · On Site Laundry · Dishwasher ·
From
$117/night
Min stay: 30 nights
Property
Condo · 2 Beds · 1 bath
Amenities
Microwave
On Site Laundry
Dishwasher
Furnished
In Unit Laundry
Hardwood Floor
Spacious 2 bedroom apartment
10

Excellent

·
Highland Park
·
2 br
·
Sleeps 4
·
Balcony · Furnished · Dishwasher ·
From
$125/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Furnished
Dishwasher
Fitness Center
Air Conditioning
In Unit Laundry
Wifi
Oven
Other spaces
Balcony, Kitchen
Private Two level Apartment easy accessible to Hospitals and University areas

No rating

·
Highland Park
·
2 br
·
Sleeps 4
·
In Unit Laundry · Balcony · Beach ·
From
$144/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
In Unit Laundry
Beach
Furnished
Wifi
Air Conditioning
Oven
Dishwasher
Other spaces
Balcony, Workspace, Kitchen
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Updated: September 19, 2023