Wooster Square vacation rentals

We found 66 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 42 options available in this historic neighborhood known for its charming streets and proximity to local eateries and parks. These apartments typically feature modern amenities such as fully equipped kitchens, comfortable living spaces, and some even include outdoor balconies for enjoying the pleasant atmosphere of the area. Additionally, there are several vacation houses and condos available, which cater to families or larger groups seeking extra space. These properties often come with multiple bedrooms, inviting living areas, and outdoor spaces, making them ideal for gatherings.
Are there any beach house rentals in Wooster Square?
In Wooster Square, Connecticut, there are several beach house rentals available, primarily situated near the picturesque Wooster Square Park and the vibrant local community. These rentals typically feature a range of amenities, including fully equipped kitchens, comfortable living spaces, and outdoor areas for relaxation. The homes often reflect the charm of the neighborhood, with some offering access to private gardens or patios, making them ideal for families or groups looking to enjoy the area's parks, eateries, and nearby attractions.
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, vacation rentals typically feature a variety of amenities that enhance the stay for travelers. Many properties include fully equipped kitchens, allowing guests to prepare their own meals, and often come with a coffee and tea maker for a convenient morning routine. Onsite parking is also commonly available, making it easier for visitors who are driving. Additional amenities such as blenders and dining areas contribute to a comfortable and home-like atmosphere.
Are there any family house rentals in Wooster Square?
In Wooster Square, Connecticut, there are some family-friendly house rentals available, making it a great choice for groups visiting the area. This charming neighborhood is known for its historic ambiance and proximity to local attractions. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the fresh air.

Visitors will appreciate the convenience of amenities like Wi-Fi and air conditioning, ensuring a comfortable stay. The neighborhood is also famous for its beautiful parks, such as Wooster Square Park, where families can relax, have picnics, or participate in community events. Additionally, the local culinary scene features renowned pizza spots and eateries, great for family outings.
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 historic architecture and beautiful park, making it an appealing choice for travelers. Many of the available properties come with amenities such as private pools, outdoor patios, and hot tubs, superb for relaxation after a day of exploring the area. Additionally, these homes often include full kitchens and spacious living areas, providing a comfortable setting for families or groups.
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.
Are there pet-friendly vacation rentals in Wooster Square?
Yes, there are several pet-friendly vacation rentals available in Wooster Square, Connecticut. This charming neighborhood is known for its historic architecture and beautiful parks, making it an excellent choice for travelers with pets. Many of the vacation rentals here offer modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.

The nearby Wooster Square Park is a highlight, providing a lovely green space superb for walks and outdoor activities with your furry friends. Additionally, the area features pet-friendly cafes and local shops that welcome pets, ideal for visitors traveling with their companions.
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?
September is the most popular time to visit Wooster Square, as the summer heat begins to wane and the fall colors start to emerge. This month attracts visitors seeking to enjoy the vibrant local culture, particularly the renowned Wooster Square Cherry Blossom Festival, which showcases the area's stunning gardens and historic architecture.

The peak season typically spans from July to September, when travelers flock to the area to take advantage of pleasant temperatures, ranging from the mid-60s to the low 80s Fahrenheit. This is an ideal time for outdoor activities, including leisurely strolls through the picturesque parks and enjoying the local eateries that showcase Connecticut's culinary delights.

For those looking for a more budget-friendly option, May tends to be a quieter month. While the weather is warm and inviting, it offers a more relaxed atmosphere superb for exploring the charming streets and indulging in the local food scene without the hustle and bustle of peak season.

Ultimately, your choice of when to visit Wooster Square will depend on whether you prefer the lively ambiance of summer or the tranquil beauty of spring.
Are there any remote work vacation rentals in Wooster Square?
In Wooster Square, Connecticut, there are a variety of remote work vacation rentals available, with around 38 options to choose from. This charming neighborhood is known for its picturesque parks and historic architecture, providing a pleasant backdrop for both work and leisure. Many of the rentals come equipped with essential remote work amenities, including high-speed Wi-Fi, dedicated desk spaces, comfortable desk chairs, and even laptop workstations. Some properties may also offer additional features like safes for security, computer monitors for enhanced productivity, and office setups designed for convenience.

Located near popular attractions such as the Wooster Square Park, famous for its cherry blossoms in spring, and a range of local eateries, these rentals allow for a great balance between work and exploration. 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?
In Wooster Square, visitors can experience a charming neighborhood known for its historic architecture and vibrant community. The area is famous for its beautiful Wooster Square Park, which is particularly popular during the cherry blossom season, offering picturesque views and a lovely spot for picnics. Vacation rentals here often provide easy access to local eateries, especially the renowned pizzerias that the neighborhood is known for, making it a culinary delight for visitors.

Additionally, Wooster Square is located near the cultural attractions of downtown New Haven, where travelers can explore Yale University and its art galleries, museums, and theaters.
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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