Wooster Square vacation rentals

We found 72 vacation rentals — enter your dates for availability

Discover a selection of 19 apartments and other vacation rentals in Wooster Square that are perfect for your trip. Vacation rentals provide the amenities you need and want for your stay with friends, family, or just your pet, like WiFi and a washer and dryer. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.

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Find out more about Wooster Square

Why visit Wooster Square

  • Historical Charm: Explore the rich history of Wooster Square, surrounded by historic colleges and universities.
  • Delicious Cuisine: Savor the famous New Haven pizza and other mouthwatering local dishes.
  • Beautiful Parks: Enjoy the scenic beauty of urban parks, perfect for outdoor activities and family outings.
  • Vibrant Community: Experience the friendly atmosphere and engage with welcoming locals in a charming neighborhood.
  • Diverse Accommodations: Choose from a range of budget-friendly vacation rentals, including cozy homes and modern apartments.

Popular types of accommodation around Wooster Square

Discover your perfect getaway in Wooster Square with Vrbo's diverse selection of vacation rentals. Whether you're looking for cozy houses, charming cottages, or modern apartments, we have something for everyone. Popular options include Haven Apartments and new New Haven apartments, as well as Whit Apartments. With transparent pricing and great savings, your ideal stay in Wooster Square awaits.

  • Houses: The top choice for visitors in Wooster Square, offering spacious and comfortable settings for families or groups.
  • Cottages: A charming option, these cozy retreats provide a quaint atmosphere for a relaxing getaway.
  • Apartments: Ideal for solo travelers or couples, apartments offer convenient amenities and a home-like feel.
  • Condos: These modern residences combine luxury with convenience, perfect for short or extended stays.
  • Villas: A lavish choice for those seeking upscale accommodations with ample space and privacy.**

Top attractions near Wooster Square

Wooster Square is an ideal destination for outdoor enthusiasts and families alike, offering a blend of history and adventure. Visitors can explore nearby historic colleges and universities, enjoy the scenic beauty of urban parks, or relax at the local beach. With a variety of cultural experiences and family-friendly activities, Wooster Square promises a fulfilling vacation for all travelers seeking to immerse themselves in the charm of New Haven.

  • Yale University: A prestigious institution with stunning architecture and rich history. Explore its museums, libraries, and beautiful campus, soaking in the vibrant academic culture.
  • Yale Bowl: A historic sports stadium that hosts Yale football games and other events. Experience the excitement of college sports in a venue steeped in tradition.
  • New Haven Green: A picturesque urban park perfect for families and outdoor activities. Enjoy picnics, concerts, and community events in this central city hub.

Things to do recommended for couples

For a romantic getaway in Wooster Square, catch a concert at Woolsey Hall, just 0.6 miles away, or sip wine at Gouveia Winery, 12 miles away. If you're feeling adventurous, hit the slopes at Powder Ridge Mountain Park, located 16 miles from your cozy retreat.

Things to do recommended for families

Your family can enjoy a day at the Connecticut Sportsplex for some active fun, relax at East Rock Park's scenic trails, and take a spin on the charming Lighthouse Point Carousel, all within a short drive from Wooster Square. It's a perfect mix of adventure and relaxation.

Things to do recommended for groups

Enjoy a night out at the Shubert Theater, just 0.7 miles from Wooster Square, where culture and entertainment await. For some local brews, visit Stony Creek Brewery, 6 miles away, or shop at Westfield Connecticut Post Mall, 8 miles away, perfect for family fun and city vibes.

*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 Wooster Square

If you're traveling with a group, family, or pets, or if you're planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Wooster Square with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor space for gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Wooster Square with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with amenities that cater to their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wooster Square: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring everyone feels at home.
  • Planning for a long term stay visiting Wooster Square: If you're in search of vacation rentals offering discounts for stays of a month or longer, 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 include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Wooster Square

Wooster Square in New Haven, Connecticut, is a charming neighborhood perfect for family-friendly adventures and outdoor excursions. Explore the vibrant atmosphere filled with friendly locals, delightful parks, and mouthwatering cuisine, especially the famous pizza. Nearby neighborhoods and Orchard Street offer additional experiences, making it an ideal base for discovering the rich culture and history of New Haven. Enjoy a budget-friendly vacation packed with memorable moments in this welcoming community.

  • New Haven: New Haven is a vibrant city known for its rich cultural scene and educational institutions, including the prestigious Yale University. Located in close proximity to Wooster Square, this city offers an array of attractions such as museums, theaters, and music venues. Visitors can enjoy shopping in trendy boutiques or dining at an eclectic mix of restaurants. The historic architecture adds to the charm, making it a great destination for families and culture enthusiasts alike. Don't miss the beautiful beach nearby for a relaxing day by the water.
  • West Haven: Just 3 miles from Wooster Square, West Haven is a picturesque coastal city that provides a fantastic blend of outdoor activities and cultural experiences. Known for its family-friendly environment, travelers can explore recreational areas, enjoy the scenic beaches, and visit local shops. The presence of a historic college university enhances the educational vibe of the city. Whether it’s a day at the beach or a stroll in the parks, West Haven is perfect for those looking to enjoy both relaxation and adventure.
  • Branford: Located 6 miles from Wooster Square, Branford is a charming town that offers stunning natural scenery and outdoor adventures. It’s a great spot for romantic getaways, with picturesque views of the shoreline and nearby lakes. Visitors can partake in recreational activities like hiking and skiing, depending on the season. The town's beautiful beaches and family-friendly parks make it an ideal destination for nature lovers and families looking to enjoy quality time together in a serene setting.

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner truly pays off. When you enroll in our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin saving.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient area for you to plan new travels, manage your existing itineraries, or check and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Wooster Square?
In Wooster Square, apartments are the most popular type of vacation rental, with about 29 available in this charming neighborhood known for its historic architecture and vibrant community. These apartments typically come with modern amenities, including fully equipped kitchens, comfortable living areas, and some may offer outdoor spaces like balconies to enjoy the local views. Additionally, there are several condos and vacation houses available, which provide more spacious options for families or larger groups, often featuring multiple bedrooms and private outdoor areas for relaxing.
Are there any beach house rentals in Wooster Square?
In Wooster Square, beach house rentals are available, providing a unique option for travelers looking to enjoy the coastal charm of Connecticut. While this neighborhood is primarily known for its historic homes and vibrant community, some rentals offer a cozy retreat. These beach houses typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces where guests can relax and enjoy the scenery. Located near parks and local eateries, these properties allow visitors to experience the rich culture of Wooster Square while being close to the shoreline.
How much does it cost to rent a vacation home in Wooster Square?
Prices for vacation rentals in Wooster Square 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 Wooster Square 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 Wooster Square vacation house rentals?
You can find great discounts on house rentals in Wooster Square 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 Wooster Square?
In Wooster Square, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and coffee and tea makers for a convenient morning routine. Many properties offer onsite parking, making it easy for travelers with vehicles to explore the area. Additionally, rentals often feature dedicated desk spaces for those needing to work or study during their stay, and dining areas where guests can enjoy meals together.
Can I find family house rentals in Wooster Square?
In Wooster Square, Connecticut, there are a variety of family-friendly house rentals available, with around 14 options to choose from. This charming neighborhood is known for its beautiful parks, historic architecture, and proximity to attractions like the Wooster Square Park, famous for its cherry blossoms in spring and local pizza spots that will delight both kids and adults.

Many of these homes offer spacious living areas that are superb for family gatherings, along with full kitchens where you can prepare meals together. Outdoor spaces, such as patios or gardens, can provide a safe area for children to play. Additionally, amenities like Wi-Fi and laundry facilities are often included, ensuring a comfortable and convenient stay for your family.
Can I rent a vacation home with a pool or hot tub in Wooster Square?
In Wooster Square, Connecticut, there are several vacation homes available for rent that feature pools and hot tubs. This charming neighborhood is known for its beautiful historic architecture and proximity to parks, making it an appealing destination for travelers. Many of these rentals offer amenities such as private pools, hot tubs, outdoor seating areas, and fully equipped kitchens, superb for both relaxation and family gatherings. Guests can enjoy the vibrant local culture, with nearby restaurants and shops adding to the overall experience.
Are there any Wooster Square vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Wooster Square 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 book pet-friendly vacation rentals in Wooster Square?
Yes, you can book pet-friendly vacation rentals in Wooster Square, Connecticut. This charming neighborhood is known for its picturesque parks and beautiful cherry blossom trees, providing a lovely backdrop for pet owners. Many vacation rentals here offer amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air.

Within Wooster Square, there are local parks like Wooster Square Park, which features walking paths and green spaces, great for leisurely strolls with your furry friends. The neighborhood is also home to pet-friendly cafes and restaurants, ideal for travelers looking to explore the area with their pets.
Can I find long-stay vacation rentals in Wooster Square?
A long-stay vacation rental in Wooster Square 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 Wooster Square for a vacation rental?
The best time to visit Wooster Square for a vacation rental is during the enchanting month of September. As summer transitions to fall, this period attracts visitors eager to experience the vibrant setting and stunning scenery of the area. Peak tourist activity typically spans from July to September, when travelers flock to enjoy the delightful weather and local festivals, particularly the famous Wooster Square Cherry Blossom Festival.

Throughout September, visitors can relish mild temperatures ranging from the low 50s to mid-70s Fahrenheit, making it an ideal time for outdoor activities like strolling through the charming streets, exploring the historic architecture, or indulging in the local cuisine at nearby cafes and eateries. The comfortable climate enhances the enjoyment of leisurely walks or picnics in the beautiful parks.

For those mindful of travel expenses, May presents a wonderful opportunity to visit Wooster Square. With fewer crowds and pleasant spring weather, this month allows travelers to explore the area's blooming parks and gardens while enjoying more affordable accommodation options.
Are there any remote work vacation rentals in Wooster Square?
In Wooster Square, Connecticut, there are 26 remote work-friendly vacation rentals available for those looking to combine work and leisure. This charming neighborhood is known for its beautiful parks and historic architecture, providing a pleasant backdrop for remote work. Many of the rentals come equipped with dedicated workspaces, including desks and comfortable desk chairs, ensuring a productive environment. Additionally, travelers can expect high-speed Wi-Fi and reliable internet access, which are essential for remote work.

The area is also famous for its lovely cherry blossom trees and proximity to local attractions, such as the Wooster Square Historic District, where you'll find excellent dining options featuring the renowned New Haven-style pizza. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Wooster Square vacation rental?
Book your Wooster Square 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 Wooster Square, Connecticut, United States of America?
In Wooster Square, travelers can enjoy a variety of attractions that showcase the area's charm and history. The neighborhood is famous for its beautiful Wooster Square Park, which features lovely cherry blossom trees and a vibrant setting, especially during the annual Cherry Blossom Festival. This park is a great spot for picnics and leisurely strolls.

Nearby, visitors can explore the historic architecture, including the iconic St. Michael's Church, known for its striking design. The area is also renowned for its delicious pizza, with several local pizzerias offering a taste of the city's culinary heritage.
Can I change or cancel my Wooster Square home rental booking on Vrbo?
To find Wooster Square 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 Wooster Square 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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