Photo by Anthony Salonga
Wooster Square holiday lettings
We found 60 holiday rentals — enter your dates for availability
Discover a selection of 20 apartments and other holiday rentals in Wooster Square that are perfect for your trip. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a fireplace. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
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Find the best place to stay - Wooster Square
Downtown loft apartment in the heart of downtown New Haven.
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
The Brick Wooster Square | Yale | Skyline Deck
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
Luxurious 3BR Apartment with Premium Amenities
Sleeps 7 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
Garden Level Suite, Court Street
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Cozy Escape - Wooster Square
Sleeps 2 · 1 bedroom · 1 bathroom
8.48.4 out of 10
Very goodvery good
9 reviews(9 reviews)
The Matisse at Wooster Square | Yale | Parking
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Top rated rentals - Wooster Square
Good location, great stay overall
1010 out of 10
Exceptionalexceptional
42 reviews(42 reviews)
High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again.
Coco N.
Stayed Jun 2025
Always a pleasure
1010 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
This was our second stay here, and the apartment is as lovely as ever. Immaculately clean, comfortable, convenient, and with great air conditioning in this hot weather. We will definitely be back.
Leah H.
Stayed Jun 2018
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in Wooster Square?
In Wooster Square, apartments are the most popular type of holiday rental, with around 35 available in the area. These apartments are often situated in charming neighbourhoods, providing easy access to local attractions such as the historic Wooster Square Park and the vibrant food scene nearby. Most rooms come with amenities like fully equipped kitchens, inviting living areas, and in some cases, private balconies to enjoy the lively surroundings.
Are there any beach house rentals in Wooster Square?
In Wooster Square, Connecticut, there are beach house rentals available, primarily situated near the waterfront. These properties typically offer a comfortable and inclusive setting, with amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios for enjoying the nearby views. The area is known for its charming neighbourhood, featuring lovely parks and proximity to local attractions, including the historic Wooster Square Park and a variety of restaurants.
How much does it cost to rent a holiday home in Wooster Square?
Prices for holiday 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 holiday 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 comforting start to the day. Many properties also offer onsite parking, making it convenient for those travelling by car. Additionally, some rentals permit pets, accommodating travellers who wish to bring their furry companions along, while service animals are also welcome.
Are there any family house rentals in Wooster Square?
In Wooster Square, Connecticut, there are numerous family-friendly house rentals available, with around 18 properties to choose from. This charming neighbourhood is known for its historic architecture and vibrant community, making it an excellent choice for families. Many of these homes offer spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the fresh air.
Can I rent a holiday home with a pool or hot tub in Wooster Square?
In Wooster Square, Connecticut, there are several holiday homes available for rent that feature pools and potentially hot tubs, providing a great option for travellers seeking relaxation and comfort during their stay. This charming neighbourhood, known for its historic architecture and vibrant community, offers a mix of amenities in its rentals. Expect to find homes with private pools, outdoor spaces ideal for gatherings, and fully equipped kitchens for home-cooked meals. Many properties also include air conditioning and Wi-Fi, ensuring a pleasant and convenient experience for guests.
Are there any Wooster Square holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Wooster Square 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.
Are there pet-friendly holiday rentals in Wooster Square?
In Wooster Square, visitors can indeed find a variety of pet-friendly holiday rentals, with around 19 options available to choose from. These accommodations often feature modern amenities such as fully equipped kitchens, spacious living areas, and sometimes private outdoor spaces, making them superbly suited for travellers with pets. The charming neighbourhood is known for its beautiful parks and historic architecture, providing a pleasant environment for leisurely strolls with your furry companions. Nearby, Wooster Square Park offers lovely green spaces and walking paths, ideal for enjoying the outdoors with pets.
Can I find long-stay holiday rentals in Wooster Square?
A long-stay holiday rental in Wooster Square 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 Wooster Square for a holiday rental?
September is the most popular time to visit Wooster Square, as the summer crowds start to wane and the area comes alive with early autumn charm. The peak season runs from July to September, with visitors flocking to experience the vibrant atmosphere, especially during the famous Wooster Square Cherry Blossom Festival in early April, which captures the hearts of many.
As summer transitions into autumn, September typically enjoys pleasant temperatures averaging in the mid-teens Celsius, creating comfortable conditions for outdoor activities such as strolling through the historic district and sampling the local cuisine. The nearby parks and gardens bloom with colour, making it an idyllic time for sightseeing and enjoying al fresco dining at charming cafes.
If you're looking for a more budget-friendly option, consider visiting in May, when the area is less crowded yet equally appealing. This month offers a lovely springtime experience, with blooming flowers and a chance to explore the local art scene without the hustle and bustle of peak tourist activity.
Are there any remote work holiday rentals in Wooster Square?
In Wooster Square, Connecticut, there are numerous holiday rentals suitable for remote work, with around 31 options available. This vibrant neighbourhood, known for its charming historic homes and beautiful cherry blossom trees, provides a conducive environment for productivity. Many of the properties feature dedicated office spaces or laptop workstations, ensuring a comfortable setting for work. Amenities commonly found in these rentals include high-speed Wi-Fi, desks with ergonomic chairs, and additional conveniences such as safes and computer monitors. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Wooster Square holiday rental?
Book your Wooster Square 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.
What are the top attractions in Wooster Square?
In Wooster Square, visitors can enjoy a charming neighbourhood known for its historic architecture and vibrant community atmosphere. The area is famous for its beautiful cherry blossom trees, which bloom spectacularly in spring, making it a picturesque spot for a stroll. A highlight of Wooster Square is the Wooster Square Park, which is ideal for picnics and leisurely walks. The neighbourhood is also renowned for its delicious pizza, with several local pizzerias that draw both residents and visitors alike.
Can I change or cancel my Wooster Square home rental booking on Vrbo?
To find Wooster Square 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Wooster Square 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.