Vacation Rentals in Woolsey Hall, CT: Compare 10+ Sites & Save

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379 Best Vacation Rentals in Woolsey Hall (Starting from $144)

Charming Studio Near Yale Downtown New Haven
Charming Studio Near Yale Downtown New Haven
Apartment
New Haven, CT, USA
0.5k from Woolsey Hall center

Apartments, Accommodations, Lodgings, Places to stay

3 Bedrooms2 Guests
3.0

Review score

1 reviews

$180
Average price / night
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“Elm City” Retreat Near Yale, Parking, Gym, Downtown, Wooster Sq & Union Station
“Elm City” Retreat Near Yale, Parking, Gym, Downtown, Wooster Sq & Union Station
Apartment
New Haven, CT, 06511, United States
0.4k from Woolsey Hall center

AC, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$393
Average price / night
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Perfect Downtown Stay Yale Walk Sallys Apizza
Perfect Downtown Stay Yale Walk Sallys Apizza
Apartment
New Haven, CT, USA
0.5k from Woolsey Hall center

Internet, Security/Safety, Air Conditioner, Pet Friendly

1 Bedroom2 Guests
New to Booking
$146
Average price / night
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Prime Yale Studio Steps to Sallys Apizza
Prime Yale Studio Steps to Sallys Apizza
Apartment
New Haven, CT, 06511, United States
0.5k from Woolsey Hall center

AC, Dryer, Heater, Internet, Microwave, No Smoking, TV, Washer

New to Booking
$200
Average price / night
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Spacious Stay near Yale in Downtown New Haven
Spacious Stay near Yale in Downtown New Haven
Apartment
New Haven, CT, USA
0.6k from Woolsey Hall center

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

6 Bedrooms16 Guests
8.6

Fabulous

112 reviews

$244
Average price / night
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Bright Downtown Room near Yale & East Rock!
Bright Downtown Room near Yale & East Rock!
Apartment
New Haven, CT, 06511, United States
0.5k from Woolsey Hall center

AC, Dryer, Heater, Internet, Microwave, No Smoking, TV, Washer

New to Booking
$154
Average price / night
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Downtown Haven Walk to Yale Renovated Parking
Downtown Haven Walk to Yale Renovated Parking
Apartment
New Haven, CT, USA
0.6k from Woolsey Hall center

Internet, Air Conditioner, Security/Safety, Pet Friendly, Parking, Child Friendly

1 Bedroom9 Guests
New to Booking
$414
Average price / night
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Penthouse Apartment at Yale University.
Penthouse Apartment at Yale University.
Apartment
New Haven, CT, 06510, United States
0.5k from Woolsey Hall center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

106 reviews

$343
Average price / night
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Modern New Haven Condo Less Than 1 Mi to Downtown!
Modern New Haven Condo Less Than 1 Mi to Downtown!
Apartment
New Haven, CT, USA
0.7k from Woolsey Hall center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Condos

3 Bedrooms6 Guests
6.5

Good

4 reviews

$252
Average price / night
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DTWN I Near Yale I King Beds I  Free Parking I Gym I Free Coffee I Pets Welcome!
DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!
Apartment
New Haven, CT, 06511, United States
0.6k from Woolsey Hall center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$364
Average price / night
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Modern & Spacious 2BR Apartment with Gym & Parking
Modern & Spacious 2BR Apartment with Gym & Parking
Apartment
New Haven, CT, USA
0.7k from Woolsey Hall center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$394
Average price / night
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Downtown Groups | Walk to Yale | Backyard +Parking
Downtown Groups | Walk to Yale | Backyard +Parking
House
New Haven, CT, 06511, United States
0.6k from Woolsey Hall center

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

4 Bedrooms11 Guests
New to Booking
$561
Average price / night
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Home Haven, Walk to Little Italy & Wooster Square
Home Haven, Walk to Little Italy & Wooster Square
Apartment
New Haven, CT, USA
0.8k from Woolsey Hall 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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Landing | Spectacular 1BD, Gym
Landing | Spectacular 1BD, Gym
Apartment
New Haven, CT, 06510, United States
0.6k from Woolsey Hall center

AC, Heater, Internet, Kitchen, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$170
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
0.8k from Woolsey Hall 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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Landing | Incredible 1BD, Gym
Landing | Incredible 1BD, Gym
Apartment
New Haven, CT, 06510, United States
0.6k from Woolsey Hall center

AC, Heater, Internet, Kitchen, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$144
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
0.8k from Woolsey Hall 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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Landing | Chic 1BD, Gym
Landing | Chic 1BD, Gym
Apartment
New Haven, CT, 06510, United States
0.6k from Woolsey Hall center

AC, Heater, Internet, Kitchen, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$180
Average price / night
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CoHouse New Haven steps to Yale University
CoHouse New Haven steps to Yale University
Apartment
New Haven, CT, USA
0.8k from Woolsey Hall center

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

7 Bedrooms15 Guests
9.1

Superb

33 reviews

$195
Average price / night
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Stylish Yale Wooster Square Downtown Laundry
Stylish Yale Wooster Square Downtown Laundry
Apartment
New Haven, CT, USA
0.8k from Woolsey Hall 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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Landing | Modern 1BD, Gym
Landing | Modern 1BD, Gym
Apartment
New Haven, CT, 06510, United States
0.6k from Woolsey Hall center

AC, Heater, Internet, Kitchen, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$162
Average price / night
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DTWN Yale Wooster Square Laundry
DTWN Yale Wooster Square Laundry
Apartment
New Haven, CT, USA
0.8k from Woolsey Hall 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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Spacious Stay Downtown New Haven
Spacious Stay Downtown New Haven
Apartment
New Haven, CT, 06510, United States
0.6k from Woolsey Hall center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$321
Average price / night
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Beautiful Downtown New Haven Retreat
Beautiful Downtown New Haven Retreat
Apartment
New Haven, CT, 06510, United States
0.6k from Woolsey Hall center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$321
Average price / night
Check Availability
Bright Downtown New Haven Escape
Bright Downtown New Haven Escape
Apartment
New Haven, CT, 06510, United States
0.6k from Woolsey Hall center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$316
Average price / night
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Modern Studio Stay On Howe
Modern Studio Stay On Howe
Apartment
New Haven, CT, 06511, United States
0.7k from Woolsey Hall center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
9.0

Fabulous

4 reviews

$157
Average price / night
Check Availability
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
0.7k from Woolsey Hall center

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

4 Bedrooms8 Guests
New to Booking
$376
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 Vacation Rentals in Woolsey Hall.

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Woolsey Hall Vacation Rentals on the Map

Frequently Asked Questions

You can explore 379 verified vacation rentals in Woolsey Hall. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Woolsey Hall vary depending on the season, property size, and location. Rates typically start from around $144 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Woolsey Hall include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Woolsey Hall welcome pets. Currently, 56 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Woolsey Hall often include amenities such as Fireplace/Heating, Guest Services, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.