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Wooster Square, New Haven, Connecticut, United States of America

Wooster Square holiday rentals

We found 181 holiday rentals — enter your dates for availability

Discover a selection of 181 holiday home rentals in Wooster Square that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at AU$ 175 per night, and holiday houses and flats & apartments are popular options for a stay in Wooster Square. Either way, you'll find holiday accommodation for everyone's needs.
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Houses

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Condos/Apartments

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Studios

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Hotels

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Find the best place to stay — Wooster Square

1 BR in Perfect Location to Yale, Downtown & Pizza

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 245 avg/night
(7)

NEW 1 Bedroom in Downtown NewHaven - Wooster Sq

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 175 avg/night
(1)

Beachfront Year-round Property - Newly Renovated

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
AU$ 505 avg/night
(31)

Cute country cottage for getaway stay

Sleeps 3 · 1 Bedroom · 1 Bathroom
AU$ 267 avg/night
(52)

Beautiful Beach House with Private Beach Access.

Sleeps 8 · 4 Bedrooms · 1 Bathroom
AU$ 435 avg/night
(33)

Search 181 holiday rentals

Top rated rentals — Wooster Square
Stayed Apr 2021

We enjoyed our stay here

Porch very nice to sit on, short walk to the beach. It's decorated very nicely. The beds were comfortable. There are restaurants you can walk to. We went to Lenny's and The Stand and had a drink and listened to music. My son really liked the loaded c...

Elaine M.
Elaine M.
Stayed Apr 2021

Absolutely amazing

Although the place was small OT had everything we needed and then some. We have stayed at several VRBO properties in the past and this one was by far the best. All the amenities were top notch and all the accessories were as well. Beautiful sheets an...

Andy H.
Andy H.
Stayed Apr 2021

Incredible home for our memorable Wedding weekend!

Our stay at the Bassett House was extraordinary. The home and amenities are even better than described! There is so much attention to detail in the decor and such thoughtfulness that went into planning for visitors. Not only was it spotless, but ther...

Mary P.
Mary P.
Stayed Apr 2021

Fabulous place

Chris' property was everything we wanted and more. Covid vaccines allowed adult siblings--New Haven natives--to reunite after a year of no travel. A few of our children joined us and there was room to spread out, spaces to be together as a family, a ...

Lois W.
Lois W.

Takoma Park, MD

Stayed Apr 2021

Gorgeous property!

What a perfect cottage! Plenty of room and so comfortable. The shower is luxurious with great pressure. So peaceful to watch the birds during sunrise over coffee. Sharon is the ideal balance of respecting privacy while also being incredibly responsiv...

terri j.
terri j.
Stayed Mar 2021

A Beauty in Branford

Awesome stay. Idyllic location. Amazing views. Kitchen has everything needed & appliances are top notch. Beds are so comfortable which is not something we usually say when on vacation. Had the best sleep each night. The owner responded quickly with q...

Colleen G.
Colleen G.
Stayed Jan 2021

Remarkable Penthouse Apt.

I greatly enjoyed my stay. Marc, the owner, is a pleasure to work with. He thought of everything and even stocked the refrigerator! The location is great for walking to get coffee and bagels in the morning or Italian food at night. Overall great expe...

Steven H.
Steven H.
Stayed Dec 2020

Winter getaway

We really enjoyed our "not traditional beach vacation" in December. House is perfectly positioned on a long stretch of a sandy beach. Upstairs apartment is very cozy and clean. Kitchen is nice size and well stocked with cooking utensils. Views are am...

PETER F.
PETER F.
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How many holiday accommodation are available around Wooster Square?

Our 2021 accommodation listings offer a large selection of 181 holiday rentals around Wooster Square. From 85 holiday houses to 79 flats & apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Wooster Square is on Stayz.