Highland Park holiday lettings

We found 71 holiday rentals — enter your dates for availability

Discover a selection of 11 homes, 16 apartments and other holiday rentals in Highland Park that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as air conditioning and cable TV. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Highland Park

Showing deals for:6 Mar - 13 Mar

Image gallery for Fresh Modern City Loft Apt! Easy Access to the city!

Open City Loft with sleeper sofa
9.8 out of 10, Exceptional, (83 reviews)
Exceptional
(83 reviews)

Fresh Modern City Loft Apt! Easy Access to the city!

Boston, MA

7% off
Price is £1,120
for 7 nights, 1 apartment
£160 per night
includes taxes & fees
Fresh Modern City Loft Apt! Easy Access to the city!

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental in Highland Park?
In Highland Park, holiday houses are quite popular, with several available throughout the area. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor areas ideal for relaxing. Many are set in tranquil neighbourhoods, providing a peaceful retreat for families or groups exploring the local parks and nature trails. Additionally, there are several apartments and condos that offer a more compact living option, often including amenities like modern kitchen appliances and shared facilities such as pools or fitness centres.
How much does it cost to rent a holiday home in Highland Park?
Prices for holiday rentals in Highland Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Highland Park to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Highland Park holiday house rentals?
You can find great discounts on house rentals in Highland Park on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Highland Park?
In Highland Park, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and coffee or tea makers for a comforting start to the day. Many rentals also feature dedicated office spaces, ideal for those needing to work remotely during their stay. Properties often boast kitchen islands, providing additional prep space and a casual dining area. Outdoor patios are also common, offering a pleasant spot to relax and enjoy the fresh air.
Are there any family house rentals in Highland Park?
In Highland Park, Massachusetts, there are several family-friendly house rentals available, providing a comfortable base for visitors. The area boasts a variety of homes that cater to families, featuring spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can enjoy themselves. Many properties also come with amenities such as Wi-Fi and laundry facilities, ensuring a convenient and enjoyable stay.
Are there any Highland Park holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Highland Park with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Highland Park?
A long-stay holiday rental in Highland Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Highland Park for a holiday rental?
The peak season for visiting Highland Park falls between May and July, with July being the most popular month for travellers seeking a vibrant holiday experience. This lively period is ideal for those who enjoy outdoor activities, as the warmer temperatures invite exploration of the local parks and waterfront areas. Expect pleasant climate conditions, typically ranging from the mid-20s to low 30s Celsius, great for leisurely strolls and picnics by the water.

During these summer months, the area buzzes with a variety of events and activities, making it an exciting time for families and friends to gather. The local community often hosts events that showcase the charm of Highland Park, providing ample opportunities for sightseeing and relaxation.

For those looking for a more budget-friendly option, consider planning your visit in December. While it's a quieter time, it offers a great experience with the holiday festivities, showcasing the town's charming decorations and seasonal events. This month allows for a different kind of exploration, with scenic winter walks and cosy indoor activities.
Are there any remote work holiday rentals in Highland Park?
In Highland Park, Massachusetts, there are a variety of remote work holiday rentals available, with around 16 options to choose from. This charming area offers a peaceful environment that is conducive to productivity. Many of the properties are equipped with essential amenities for remote work, including Wi-Fi, dedicated desks, comfortable office chairs, and even computer monitors in some cases. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Highland Park holiday rental?
Book your Highland Park holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Highland Park home rental booking on Vrbo?
To find Highland Park holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Highland Park holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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