Squirrel Hill vacation rentals

We found 129 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Squirrel Hill that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll have the amenities you expect and more, which might include a hot tub and garden. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

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Find out more about Squirrel Hill

Why visit Squirrel Hill

  • Cultural richness: Squirrel Hill is known for its vibrant cultural scene, making it ideal for family vacations.
  • Charming local shops: Explore a variety of unique boutiques and eateries that reflect the neighborhood's welcoming atmosphere.
  • Beautiful parks: Enjoy scenic views and outdoor activities in the many parks scattered throughout Squirrel Hill.
  • Community events: Participate in local events and gatherings that showcase the friendly spirit of the area.
  • Diverse accommodation options: Choose from cozy apartments, charming cottages, or spacious vacation homes for a comfortable stay.

Popular types of accommodation around Squirrel Hill

Looking for the perfect getaway in Squirrel Hill? You're in the right place. Our most popular vacation rental options include houses, cozy apartments, and charming cottages. Whether you’re searching for a spacious house rental or a stylish apartment in Squirrel Hill, we have a variety of choices to meet your needs. Discover the comfort and convenience of Squirrel Hill, PA, where your ideal home away from home awaits.

  • Houses: The top choice for visitors to Squirrel Hill, offering spacious and comfortable accommodations perfect for families or groups.
  • Apartments: A popular option for travelers seeking convenient locations and modern amenities, ideal for solo adventurers or couples.
  • Cottages: A charming and cozy option, perfect for those wanting a quaint and peaceful retreat during their stay.
  • Cabins: These rustic hideaways provide a unique experience for nature enthusiasts looking to unwind.
  • Condos: A versatile choice that combines comfort and style, appealing to those who appreciate a home-like atmosphere.**

Top attractions in and around Squirrel Hill

Squirrel Hill, Pittsburgh, is perfect for a city-themed family vacation rich in culture. Visitors can explore modern colleges and universities, enjoy events at entertainment arenas, and attend conferences at local venues. This charming neighborhood offers a variety of attractions that cater to travelers seeking cultural experiences and family-friendly activities. Make sure to immerse yourself in the vibrant community during your visit.

  • Carnegie Mellon University: Known for its cutting-edge research and innovation, Carnegie Mellon University boasts a vibrant campus atmosphere surrounded by city life. Visitors can explore beautiful architecture and a lively student community, making it a unique educational experience.
  • PPG Paints Arena: Just 3 miles away, this state-of-the-art arena hosts thrilling sports events and concerts. With family-friendly activities and an energetic atmosphere, it’s a hub for entertainment in Pittsburgh.
  • David L Lawrence Convention Center: Located 4 miles away, this modern venue is perfect for conferences and exhibitions, offering a professional environment infused with business energy and innovative design.

Things to do recommended for couples

For a romantic getaway in Squirrel Hill, enjoy a scenic ride on the Monongahela Incline, savor luxury at the Oakmont Country Club, or catch a lively show at the Rex Theater. Each experience adds a unique charm to your couple's vacation in Pittsburgh.

Things to do recommended for families

Families will love the excitement at Sandcastle Water Park, only 3 miles from Squirrel Hill, perfect for adventure and fun. Additionally, Schenley Park, just 1 mile away, offers a peaceful space for relaxation, while Acrisure Stadium, 5 miles away, provides thrilling sports experiences.

Things to do recommended for groups

Group travelers in Squirrel Hill can enjoy shopping and entertainment at The Waterfront, embark on an adventurous hike along the Three Rivers Heritage Trail, and experience cultural performances at the nearby Kelly Strayhorn Theater, all while soaking up the vibrant local atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Squirrel Hill

If you're traveling with a group, family, or pets, or if you're looking for extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Squirrel Hill with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, Vrbo allows you to easily filter for these features and plenty more.
  • Traveling to Squirrel Hill with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about your location in relation to family-friendly attractions is a wise choice.
  • Taking your pets with you to Squirrel Hill: For many families, a vacation isn’t truly fulfilling without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Squirrel Hill: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Squirrel Hill

Squirrel Hill, a vibrant neighborhood in Pittsburgh, offers a delightful blend of family-friendly activities and cultural experiences. Known for its welcoming atmosphere and scenic views, visitors can explore charming local shops, parks, and eateries. Just a short distance away, the surrounding areas provide a taste of urban life with a friendly vibe. Whether you're wandering through Squirrel Hill South or enjoying the community spirit, this destination promises memorable moments for every traveler.

  • Pittsburgh: Pittsburgh is a vibrant metropolis known for its rich history and cultural diversity. Nestled in the heart of western Pennsylvania, Squirrel Hill is a charming neighborhood within this dynamic city. Visitors to Pittsburgh can enjoy a variety of experiences, from outdoor activities in scenic parks to family-friendly attractions. The city is home to notable landmarks such as sports stadiums and modern universities, making it an ideal destination for sports fans and academics alike. With its blend of urban life and natural beauty, Pittsburgh offers something for everyone.
  • Downtown Pittsburgh: Located just 4 miles from Squirrel Hill, Downtown Pittsburgh is the bustling heart of the city. This neighborhood is perfect for travelers seeking a mix of family entertainment and sports experiences. Downtown features a range of attractions, including arena entertainment facilities and urban parks, where visitors can enjoy outdoor activities in a lively atmosphere. With its vibrant shopping malls and access to major sports venues, Downtown Pittsburgh is an essential stop for anyone looking to immerse themselves in the city's lively culture.
  • Shadyside: Only 0.7 miles from Squirrel Hill, Shadyside is a charming neighborhood known for its upscale shopping and dining options. This area attracts both families and business travelers, offering a unique blend of city-themed experiences. Visitors can explore local boutiques and enjoy meals at diverse restaurants while being in proximity to educational institutions and sports facilities. Shadyside’s inviting atmosphere and vibrant community make it a delightful area to visit on your Pittsburgh vacation.

Best time to go to Squirrel Hill

If you're planning a trip to Squirrel Hill, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and October, while off-peak times, like February, May and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.6°F (-1.9°C)Light RainMostly CloudyAverageSlightly Low
February31.3°F (-0.4°C)Light RainMostly CloudyLowSlightly Low
March40.5°F (4.7°C)Light RainMostly CloudyAverageSlightly Low
April51.1°F (10.6°C)Light RainMostly CloudyHighAverage
May61.7°F (16.5°C)Light RainMostly SunnyLowAverage
June69.4°F (20.8°C)Light RainMostly SunnyAverageSlightly High
July73.9°F (23.3°C)Light RainMostly SunnyHighAverage
August72.1°F (22.3°C)Light RainMostly SunnyAverageAverage
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October54.7°F (12.6°C)Light RainMostly SunnyHighSlightly High
November42.6°F (5.9°C)Light RainMostly SunnyAverageSlightly High
December35.2°F (1.8°C)Light RainMostly CloudyLowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Plus, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, feel free to use our filters to narrow down your search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. It truly benefits you to take on the role of organizer. Become a part of our One Key rewards program to enjoy exclusive savings for members and earn OneKeyCash on qualifying stays. Sign up today and start reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is designed to help you plan your trips with ease. You can create new itineraries, refine your existing plans, or manage your reservations all in one place. Your saved and booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Squirrel Hill?
In Squirrel Hill, vacation houses and apartments are both popular choices, with several of each type available throughout the neighborhood. These rentals are typically situated in a charming, residential setting, providing a cozy atmosphere for visitors. Most apartments come equipped with fully functional kitchens, comfortable living spaces, and amenities like Wi-Fi and laundry facilities. Vacation houses generally offer more space, featuring multiple bedrooms, private yards, and outdoor seating areas, which are ideal for families or groups looking to relax and enjoy the local charm.
How much does it cost to rent a vacation home in Squirrel Hill?
Prices for vacation rentals in Squirrel Hill 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 Squirrel Hill 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 Squirrel Hill vacation house rentals?
You can find great discounts on house rentals in Squirrel Hill 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 Squirrel Hill?
In Squirrel Hill, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals and enjoy the convenience of home cooking. Many rentals also feature designated workspaces, complete with desks for those needing to catch up on work or study during their stay. Onsite parking is another sought-after amenity, making it easy for travelers with vehicles to access the area without hassle. Additionally, families traveling with young children can expect rentals equipped with travel cribs, ensuring a comfortable stay for little ones. Many properties also provide coffee and tea makers, great for guests looking to enjoy a warm beverage in the comfort of their rental.
Can I find family house rentals in Squirrel Hill?
In Squirrel Hill, Pennsylvania, there are several family-friendly house rentals available, making it a great choice for those traveling with kids. This neighborhood is known for its tree-lined streets and proximity to parks, such as Schenley Park, which offers playgrounds, sports facilities, and scenic walking trails. Many of the homes in this area provide spacious living rooms, fully equipped kitchens for family meals, and outdoor areas where children can play safely.

Visitors will appreciate amenities like Wi-Fi, air conditioning, and laundry facilities, contributing to a comfortable stay. Additionally, Squirrel Hill features a vibrant community with local shops, restaurants, and cultural attractions, ensuring that families can enjoy both relaxation and adventure during their visit.
Can I rent a vacation home with a pool or hot tub in Squirrel Hill?
In Squirrel Hill, Pennsylvania, there are several vacation homes available for rent that feature hot tubs, making it an appealing option for travelers looking for relaxation. This charming neighborhood is known for its beautiful parks and vibrant community atmosphere. Many of the vacation rentals in the area come equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where guests can unwind. Additionally, properties may include private hot tubs, allowing for a soothing experience after a day of exploring the local shops and restaurants.
Are there any Squirrel Hill vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Squirrel Hill with parking available—perfect for families or travelers 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 vacation rentals in Squirrel Hill?
A long-stay vacation rental in Squirrel Hill is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Squirrel Hill for a vacation rental?
The best time to visit Squirrel Hill for a vacation rental is during the peak season from September to November, with October being the most popular month. This delightful period showcases the vibrant fall foliage, creating a picturesque setting for outdoor activities and leisurely strolls through the neighborhood's charming parks. Visitors can enjoy the crisp autumn air while exploring local cafes, boutiques, and cultural sites, all contributing to the area's community vibe.

October in Squirrel Hill typically brings mild temperatures, ranging from the low 40s to the mid-60s Fahrenheit, making it comfortable for sightseeing and outdoor events. With a range of seasonal festivals and activities, this month offers a lively option that enhances the experience of visiting.

If you're looking for a more budget-friendly option, consider traveling in February, when the crowds are thinner and you can enjoy the tranquility of the neighborhood. While the weather may be cooler, this month provides a great opportunity for cozy indoor activities, such as visiting local art galleries and enjoying the culinary scene without the hustle and bustle of high tourist season.

Ultimately, your choice will depend on whether you prefer the vibrant energy of fall or the peaceful charm of winter in Squirrel Hill.
Are there any remote work vacation rentals in Squirrel Hill?
In Squirrel Hill, Pennsylvania, there are several remote work vacation rentals available, making it a suitable destination for those looking to combine work and leisure. Many properties in this charming neighborhood offer amenities tailored for remote workers, such as dedicated desks and high-speed Wi-Fi, ensuring a productive environment. Additionally, guests can enjoy free Wi-Fi in public areas, providing flexibility for work outside of their rental.

Squirrel Hill is known for its vibrant community, with easy access to local parks, cafes, and shops, offering plenty of opportunities for relaxation after a day of work. Travelers can expect comfortable accommodations that cater to both work and leisure needs, often featuring well-equipped kitchens, spacious living areas, and inviting atmospheres that encourage a balanced stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Squirrel Hill vacation rental?
Book your Squirrel Hill vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Squirrel Hill, Pennsylvania, United States of America?
In Squirrel Hill, visitors can enjoy a blend of cultural and recreational attractions. The neighborhood's proximity to Schenley Park offers expansive green spaces for outdoor activities such as hiking, picnicking, and sports. Within the park, you can also find the Phipps Conservatory and Botanical Gardens, which features stunning plant exhibits and seasonal displays.

The area is known for its vibrant dining scene, particularly along Murray Avenue, where you can explore a variety of cuisines, from casual eateries to more upscale dining options. Additionally, Squirrel Hill is home to the historic Frick Park, which provides more trails and open space for nature lovers.

For those interested in cultural experiences, the nearby Carnegie Library of Pittsburgh is a noteworthy landmark, offering a wealth of resources and community events.
Can I change or cancel my Squirrel Hill home rental booking on Vrbo?
To find Squirrel Hill vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Squirrel Hill vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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