Short-Term Rentals in Wooster Square, CT: Compare 10+ Sites & Save

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388 Best Short-Term Rentals in Wooster Square (Starting from $118)

The Historic Mansion
The Historic Mansion
House
New Haven, CT, USA
0.2k from Wooster Square center

B&bs, Accommodations, Parking, Guest houses, Homestays, 3-star, Lodgings, Vacation rentals, Places to stay

5 Bedrooms8 Guests
7.7

Good

183 reviews

$118
Average price / night
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Unit 101 · RENOVATED, 1 mile from YALE!
Unit 101 · RENOVATED, 1 mile from YALE!
Apartment
New Haven, CT, 06511, United States
0.1k from Wooster Square center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom3 Guests
New to Booking
$138
Average price / night
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Gorgeous 1BR Wooster Sq. apt. - wshr/dryr, parking
Gorgeous 1BR Wooster Sq. apt. - wshr/dryr, parking
Apartment
New Haven, CT, USA
0.2k from Wooster Square center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom3 Guests
9.3

Superb

24 reviews

$162
Average price / night
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Unit 102 · NEAR YALE AND DOWNTOWN  NEWLY RENOVATED
Unit 102 · NEAR YALE AND DOWNTOWN NEWLY RENOVATED
Apartment
New Haven, CT, 06511, United States
0.1k from Wooster Square center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom3 Guests
New to Booking
$171
Average price / night
Check Availability
Home Haven, Walk to Little Italy & Wooster Square
Home Haven, Walk to Little Italy & Wooster Square
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom6 Guests
9.4

Superb

12 reviews

$234
Average price / night
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The Matisse: Walk to Yale & Wooster SQ + Parking!
The Matisse: Walk to Yale & Wooster SQ + Parking!
Apartment
New Haven, CT, 06511, United States
0.1k from Wooster Square center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$338
Average price / night
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The Brick House Wooster Sq at Yale with Skyline Deck and WD
The Brick House Wooster Sq at Yale with Skyline Deck and WD
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms8 Guests
9.5

Superb

2 reviews

$589
Average price / night
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Upper Maisonette, Court Street
Upper Maisonette, Court Street
Apartment
New Haven, CT, 06511, United States
0.2k from Wooster Square center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$379
Average price / night
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The Matisse at Wooster Square Yale with Parking
The Matisse at Wooster Square Yale with Parking
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
9.0

Fabulous

1 reviews

$369
Average price / night
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Modern Stylish Unit in Wooster Sq, New Haven - This is a 29-night min booking
Modern Stylish Unit in Wooster Sq, New Haven - This is a 29-night min booking
Apartment
New Haven, CT, 06511, United States
0.2k from Wooster Square center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$525
Average price / night
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AO Destinations - Wooster Street in Little Italy New Haven
AO Destinations - Wooster Street in Little Italy New Haven
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering

2 Bedrooms10 Guests
8.1

Very Good

7 reviews

$215
Average price / night
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A brick's throw away to Sally's Apizza!
A brick's throw away to Sally's Apizza!
Apartment
New Haven, CT, 06511, United States
0.2k from Wooster Square center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

2 Bedrooms5 Guests
8.8

Fabulous

3 reviews

$320
Average price / night
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Stylish Yale Wooster Square Downtown Laundry
Stylish Yale Wooster Square Downtown Laundry
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

1 Bedroom5 Guests
8.5

Very Good

2 reviews

$229
Average price / night
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Garden Level Suite, Court Street
Garden Level Suite, Court Street
Apartment
New Haven, CT, 06511, United States
0.2k from Wooster Square center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$515
Average price / night
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DTWN Yale Wooster Square Laundry
DTWN Yale Wooster Square Laundry
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering

1 Bedroom5 Guests
9.0

Fabulous

3 reviews

$537
Average price / night
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The Brick: Rooftop Deck Home. Walk to Yale!
The Brick: Rooftop Deck Home. Walk to Yale!
Apartment
New Haven, CT, 06511, United States
0.2k from Wooster Square center

AC, Balcony, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
8.6

Fabulous

8 reviews

$474
Average price / night
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Wooster Square Gems
Wooster Square Gems
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

5 Bedrooms15 Guests
9.7

Exceptional

3 reviews

$460
Average price / night
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Cozy Stay by Little Italy & Wooster Street
Cozy Stay by Little Italy & Wooster Street
Apartment
New Haven, CT, 06511, United States
0.3k from Wooster Square center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom6 Guests
10.0

Exceptional

2 reviews

$203
Average price / night
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Central 2BR Near Yale WiFi with Washer and Dryer
Central 2BR Near Yale WiFi with Washer and Dryer
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms5 Guests
9.3

Superb

4 reviews

$188
Average price / night
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Stylish Yale at Wooster Square + Washer & Dryer
Stylish Yale at Wooster Square + Washer & Dryer
Apartment
New Haven, CT, 06511, United States
0.3k from Wooster Square center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
9.6

Exceptional

7 reviews

$568
Average price / night
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Stylish Comfort Wooster Square Yale Wi-Fi
Stylish Comfort Wooster Square Yale Wi-Fi
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

1 Bedroom5 Guests
New to Booking
$363
Average price / night
Check Availability
Modern Downtown Yale, Wooster Square apartment
Modern Downtown Yale, Wooster Square apartment
Apartment
New Haven, CT, 06511, United States
0.3k from Wooster Square center

AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
8.0

Good

2 reviews

$334
Average price / night
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Downtown Loft 1BR Near Yale University with Wifi
Downtown Loft 1BR Near Yale University with Wifi
Apartment
New Haven, CT, USA
0.3k from Wooster Square center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

1 Bedroom3 Guests
New to Booking
$303
Average price / night
Check Availability
Modern King Suite near Wooster Square and Yale
Modern King Suite near Wooster Square and Yale
Apartment
New Haven, CT, 06511, United States
0.3k from Wooster Square center

AC, Dryer, Elevator, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
8.8

Fabulous

3 reviews

$358
Average price / night
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Stylish Wooster Square Home Walk to Yale
Stylish Wooster Square Home Walk to Yale
Apartment
New Haven, CT, 06511, United States
0.3k from Wooster Square center

AC, Dryer, Elevator, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms5 Guests
9.4

Superb

3 reviews

$377
Average price / night
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Prime Yale Living in Modern Wooster Square
Prime Yale Living in Modern Wooster Square
Apartment
New Haven, CT, 06511, United States
0.3k from Wooster Square center

AC, Crib, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, TV

2 Bedrooms6 Guests
New to Booking
$271
Average price / night
Check Availability
Modern Loft near Yale and Wooster Square + Parking
Modern Loft near Yale and Wooster Square + Parking
Apartment
New Haven, CT, 06511, United States
0.3k from Wooster Square center

AC, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$280
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Wooster Square.

Where to stay in Wooster Square? Best neighborhoods & areas

Wooster Square Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 388 verified short-term rentals in Wooster Square, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Wooster Square vary depending on location, property size, and travel dates. Rates typically start from around $118 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Wooster Square include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Wooster Square, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Wooster Square often include amenities such as Pet Friendly, Guest Services, and Fireplace/Heating, providing a comfortable and convenient stay.

Short-term rentals in Wooster Square are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.