Find Vacation Rentals in Highland Park

We have 3,368 properties to choose from
Highland Park
Anytime
Guests
Highland Park
Anytime
Guests

Popular Highland Park Vacation Rentals

Find the perfect Highland Park vacation rental

Maisonette Highland Park
$175 per night
Maisonette ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Highland Park, Boston, Massachusetts, United States
Details
Vacasa
Details
Details
Accommodation Highland Park
$122 per night
Accommodation ∙ 5 guests ∙ 1 bedroom
Highland Park, Boston, Massachusetts, United States
Details
HomeToGo
Details
Details
Bed and breakfast Highland Park
$117 per night
Bed and breakfast ∙ 4 guests ∙ 2 bedrooms
Highland Park, Boston, Massachusetts, United States
Details
Vrbo
Details
Details
Apartment Highland Park
$285 per night
Apartment ∙ 11 guests ∙ 4 bedrooms
5.0
Outstanding (60 ratings)
Highland Park, Boston, Massachusetts, United States
Details
Vrbo
Details
Details
Apartment Highland Park
$433 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.7
Excellent (46 ratings)
Highland Park, Boston, Massachusetts, United States
Details
Vrbo
Details
Details
House Highland Park
$463 per night
House ∙ 14 guests ∙ 5 bedrooms
4.3
Very good (11 ratings)
Highland Park, Boston, Massachusetts, United States
Details
Vrbo
Details
Details
Condo Highland Park
$316 per night
Condo ∙ 12 guests ∙ 4 bedrooms
4.6
Excellent (5 ratings)
Highland Park, Boston, Massachusetts, United States
Details
Vrbo
Details
Details
Apartment Highland Park
$156 per night
Apartment ∙ 8 guests ∙ 1 bedroom
3.5
Good (91 ratings)
Highland Park, Boston, Massachusetts, United States
Details
Expedia
Details
Details
Apartment Highland Park
$118 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding (9 ratings)
Highland Park, Boston, Massachusetts, United States
Details
Vrbo
Details
Details
View more

Recommended Rentals With Pools

Apartment  Highland Park
$832 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Highland Park, Boston, Massachusetts, United States
Pool
Details
HomeToGo
Details
Details
Apartment  Highland Park
$943 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Highland Park, Boston, Massachusetts, United States
Pool
Details
HomeToGo
Details
Details
Apartment  Highland Park
$240 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Highland Park, Boston, Massachusetts, United States
Pool
Details
Vrbo
Details
Details
View more

Pet-Friendly Homes and Apartments

Apartment  Highland Park
$510 per night
Apartment ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (47 ratings)
Highland Park, Boston, Massachusetts, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Highland Park
$1,034 per night
House ∙ 11 guests ∙ 3 bedrooms
4.6
Excellent (29 ratings)
Highland Park, Boston, Massachusetts, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment  Highland Park
$346 per night
Apartment ∙ 9 guests ∙ 5 bedrooms
4.7
Excellent (3 ratings)
Highland Park, Boston, Massachusetts, United States
Pet-friendly
Details
Vrbo
Details
Details
View more

Best vacation rentals with a balcony

Apartment  Highland Park
$230 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (74 ratings)
Highland Park, Boston, Massachusetts, United States
Balcony
Details
Vrbo
Details
Details
Condo  Highland Park
$412 per night
Condo ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (22 ratings)
Highland Park, Boston, Massachusetts, United States
Balcony
Details
Vrbo
Details
Details
House  Highland Park
$512 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (144 ratings)
Highland Park, Boston, Massachusetts, United States
Balcony
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

How much does it cost to stay in Highland Park?

The price per night in Highland Park starts at $111.

Can I book a vacation rental in Highland Park?

Tripping.com offers great selection on vacation rentals with 3,368 offers currently available in Highland Park.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Highland

Find the best Highland vacation rentals on Tripping.com. With over 101 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Highland range from $33 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 95 homes in Highland offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 8 rentals with pool or jacuzzi, or relax with the family in one of the 90 homes with cable TV. For all those pet owners with dogs or cats, Highland offers 14 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 6 vacation rental sites in Highland where the top providers in that area are HomeAway, TripAdvisor, and RedAwning. There are 81 HomeAway rentals, 12 TripAdvisor short term rentals and 2 RedAwning vacation rentals.

Popular Day Trips Near Highland Park

Show more
image-tag