Find Vacation Rentals in Highland Park

We have 3,805 properties to choose from
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Popular Highland Park Vacation Rentals

Find the perfect Highland Park vacation rental

Apartment Highland Park
from $162 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Highland Park, Boston, Massachusetts, United States
Agoda
Details
Apartment Highland Park
from $119 per night
Apartment ∙ 4 guests ∙ 1 bedroom
3.9
Good
Highland Park, Boston, Massachusetts, United States
Agoda
Details
Condo Highland Park
from $215 per night
Condo ∙ 9 guests ∙ 4 bedrooms
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $59 per night
Apartment ∙ 2 guests ∙ 4 bedrooms
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $147 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding(13 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $231 per night
Apartment ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(57 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
House Highland Park
from $249 per night
House ∙ 14 guests ∙ 5 bedrooms
4.3
Very good(19 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $112 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $143 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(4 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
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Recommended Rentals With Pools

House  Highland Park
from $202 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(2 ratings)
Highland Park, Boston, Massachusetts, United States
Pool
Vrbo
Details
Apartment  Highland Park
from $167 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Highland Park, Boston, Massachusetts, United States
Pool
Vrbo
Details
House  Highland Park
from $231 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(2 ratings)
Highland Park, Boston, Massachusetts, United States
Pool
Vrbo
Details
View more

Pet-Friendly Homes and Apartments

Apartment  Highland Park
from $239 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(18 ratings)
Highland Park, Boston, Massachusetts, United States
Pet-friendly
Vrbo
Details
Apartment  Highland Park
from $200 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(8 ratings)
Highland Park, Boston, Massachusetts, United States
Pet-friendly
Vrbo
Details
Apartment  Highland Park
from $134 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Highland Park, Boston, Massachusetts, United States
Pet-friendly
Vrbo
Details
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Best vacation rentals with a balcony

Condo  Highland Park
from $418 per night
Condo ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(27 ratings)
Highland Park, Boston, Massachusetts, United States
Balcony
Vrbo
Details
Apartment  Highland Park
from $134 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Highland Park, Boston, Massachusetts, United States
Balcony
Vrbo
Details
House  Highland Park
from $628 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding(1 rating)
Highland Park, Boston, Massachusetts, United States
Balcony
Vrbo
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 $58.

Can I book a vacation rental in Highland Park?

Tripping.com offers great selection on vacation rentals with 3,805 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

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