Find Vacation Rentals in Highland Park

We have 4,001 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Highland Park Vacation Rentals

Find the perfect Highland Park vacation rental

Apartment Highland Park
from $147 per night
3 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(14 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $340 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

102 m² Apartment

Highland Park, Boston, Massachusetts, United States
Agoda
Details
Condo Highland Park
from $266 per night
9 guests ∙ 5 bedrooms

Condo

4.8
Outstanding(11 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $137 per night
Apartment ∙ 4 guests ∙ 1 bedroom

56 m² Apartment

3.8
Good
Highland Park, Boston, Massachusetts, United States
Agoda
Details
Apartment Highland Park
from $60 per night
2 guests ∙ 4 bedrooms

Apartment

Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $329 per night
Apartment ∙ 10 guests ∙ 4 bedrooms

125 m² Apartment

4.9
Outstanding(106 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $448 per night
11 guests ∙ 4 bedrooms

Apartment

4.9
Outstanding(69 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $180 per night
5 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(8 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Apartment Highland Park
from $422 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

112 m² Apartment

5.0
Outstanding(35 ratings)
Highland Park, Boston, Massachusetts, United States
Vrbo
Details
Show more

Recommended Rentals With Pools

Apartment  Highland Park
from $247 per night
Apartment ∙ 2 guests ∙ 1 bedroom

70 m² Apartment

Highland Park, Boston, Massachusetts, United States
Pool
Vrbo
Details
Apartment  Highland Park
from $516 per night
8 guests ∙ 2 bedrooms

Apartment

Highland Park, Boston, Massachusetts, United States
Pool
Vrbo
Details
Accommodation  Highland Park
from $376 per night
Accommodation ∙ 2 guests ∙ 1 bedroom

33 m² Accommodation

4.8
Outstanding(108 ratings)
Highland Park, Boston, Massachusetts, United States
Pool
HomeToGo
Details
Show more

Pet-Friendly Homes and Apartments

House  Highland Park
from $461 per night
10 guests ∙ 4 bedrooms

House

Highland Park, Boston, Massachusetts, United States
Pet-friendly
Vrbo
Details
Apartment  Highland Park
from $181 per night
Apartment ∙ 5 guests ∙ 4 bedrooms

70 m² Apartment

5.0
Outstanding(9 ratings)
Highland Park, Boston, Massachusetts, United States
Pet-friendly
Vrbo
Details
Apartment  Highland Park
from $622 per night
18 guests ∙ 5 bedrooms

Apartment

Highland Park, Boston, Massachusetts, United States
Pet-friendly
Vrbo
Details
Show more

Vacation rentals with a balcony

Condo  Highland Park
from $229 per night
3 guests ∙ 2 bedrooms

Condo

Highland Park, Boston, Massachusetts, United States
Balcony
Vrbo
Details
House  Highland Park
from $712 per night
14 guests ∙ 6 bedrooms

House

4.5
Excellent(6 ratings)
Highland Park, Boston, Massachusetts, United States
Balcony
Vrbo
Details
House  Highland Park
from $536 per night
16 guests ∙ 8 bedrooms

House

5.0
Outstanding(8 ratings)
Highland Park, Boston, Massachusetts, United States
Balcony
Vrbo
Details
Show more

Frequently Asked Questions

How much does it cost to stay in Highland Park?

The price per night in Highland Park starts at $60.

Can I book a vacation rental in Highland Park?

Tripping.com offers great selection on vacation rentals with 4,001 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

image-tag