Find Vacation Rentals in Highland Park

We have 3,074 properties to choose from
Highland Park
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Popular Highland Park Vacation Rentals

Find the perfect Highland Park vacation rental

Apartment Highland Park
$185 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Highland Park, Boston, Massachusetts, United States
Details
HomeToGo
Details
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House Highland Park
$93 per night
House ∙ 4 guests ∙ 2 bedrooms
Highland Park, Boston, Massachusetts, United States
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Vrbo
Details
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Apartment Highland Park
$111 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Highland Park, Boston, Massachusetts, United States
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Vrbo
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Details
Condo Highland Park
$273 per night
Condo ∙ 9 guests ∙ 4 bedrooms
Highland Park, Boston, Massachusetts, United States
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Vrbo
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Condo Highland Park
$141 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Highland Park, Boston, Massachusetts, United States
Details
Vrbo
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Details
Apartment Highland Park
$171 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Highland Park, Boston, Massachusetts, United States
Details
HomeToGo
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Apartment Highland Park
$152 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (1 rating)
Highland Park, Boston, Massachusetts, United States
Details
Vrbo
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Apartment Highland Park
$111 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.7
Excellent (51 ratings)
Highland Park, Boston, Massachusetts, United States
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Vrbo
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House Highland Park
$375 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Highland Park, Boston, Massachusetts, United States
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Vrbo
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Recommended Rentals With Pools

Apartment  Highland Park
$255 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
3.9
Good (18 ratings)
Highland Park, Boston, Massachusetts, United States
Pool
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Vrbo
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Details
House  Highland Park
$251 per night
House ∙ 4 guests ∙ 1 bedroom
Highland Park, Boston, Massachusetts, United States
Pool
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Vrbo
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House  Highland Park
$248 per night
House ∙ 8 guests ∙ 3 bedrooms
Highland Park, Boston, Massachusetts, United States
Pool
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Vrbo
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Pet-Friendly Homes and Apartments

Apartment  Highland Park
$244 per night
Apartment ∙ 5 guests ∙ 3 bedrooms
Highland Park, Boston, Massachusetts, United States
Pet-friendly
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HomeToGo
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Apartment  Highland Park
$315 per night
Apartment ∙ 14 guests ∙ 4 bedrooms
4.5
Excellent (24 ratings)
Highland Park, Boston, Massachusetts, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment  Highland Park
$182 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.7
Excellent (55 ratings)
Highland Park, Boston, Massachusetts, United States
Pet-friendly
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Vrbo
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Details
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Best vacation rentals with a balcony

Apartment  Highland Park
$248 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (13 ratings)
Highland Park, Boston, Massachusetts, United States
Balcony
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Vrbo
Details
Details
Condo  Highland Park
$405 per night
Condo ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (16 ratings)
Highland Park, Boston, Massachusetts, United States
Balcony
Details
Vrbo
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Maisonette  Highland Park
$188 per night
Maisonette ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding
Highland Park, Boston, Massachusetts, United States
Balcony
Details
Vacasa
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Frequently Asked Questions

How much does it cost to stay in Highland Park?

The price per night in Highland Park starts at $93.

Can I book a vacation rental in Highland Park?

Tripping.com offers great selection on vacation rentals with 3,072 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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