Photo by Anthony Salonga
Holiday rentals near Wooster Square
We found 392 holiday rentals — enter your dates for availability
Choose the perfect holiday home within easy reach of Wooster Square. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as cable TV and a washer and dryer. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Wooster Square
Showing deals for:31 Oct - 7 Nov
Image gallery for Historic Whitneyville Cottage
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Historic Whitneyville Cottage
Hamden, CT
7% off
Price is NZ$2,279
NZ$2,279
NZ$326 per night
includes taxes & fees
Image gallery for Spacious Modern Beach House, perfect for families and groups up to 12
1010 out of 10 rating
Exceptional
(11 reviews)
Spacious Modern Beach House, perfect for families and groups up to 12
Branford, CT
16% off
Price is NZ$7,739
NZ$7,739
NZ$1,106 per night
includes taxes & fees
Image gallery for Beautiful Waterfront Beach House for Family Vacations
1010 out of 10 rating
Exceptional
(43 reviews)
Beautiful Waterfront Beach House for Family Vacations
Branford, CT
8% off
Price is NZ$7,914
NZ$7,914
NZ$1,131 per night
includes taxes & fees
Image gallery for Bohemian Beach Oasis- Welcome to paradise and your own private beach!
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Bohemian Beach Oasis- Welcome to paradise and your own private beach!
Milford, CT
5% off
Price is NZ$5,977
NZ$5,977
NZ$854 per night
includes taxes & fees
Image gallery for Waterfront Cottage in Branford
1010 out of 10 rating
Exceptional
(95 reviews)
Waterfront Cottage in Branford
Branford, CT
8% off
Price is NZ$9,988
NZ$9,988
NZ$1,427 per night
includes taxes & fees
Image gallery for Dove Haven | Find your Peace
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Dove Haven | Find your Peace
New Haven, CT
8% off
Price is NZ$12,522
NZ$12,522
NZ$1,789 per night
includes taxes & fees
Image gallery for Direct Waterfront Private Beach Escape
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Direct Waterfront Private Beach Escape
East Haven, CT
15% off
Price is NZ$8,949
NZ$8,949
NZ$1,278 per night
includes taxes & fees
Image gallery for Beach House steps from sand & Amazing Views
1010 out of 10 rating
Exceptional
(9 reviews)
Beach House steps from sand & Amazing Views
West Haven, CT
8% off
Price is NZ$9,015
NZ$9,015
NZ$1,288 per night
includes taxes & fees
Image gallery for Clear LI Sound waterview, Wedding pics, Yale&Beach
1010 out of 10 rating
Exceptional
(5 reviews)
Clear LI Sound waterview, Wedding pics, Yale&Beach
East Haven, CT
8% off
Price is NZ$5,289
NZ$5,289
NZ$756 per night
includes taxes & fees
Image gallery for Sleeping Giant Getaway w/ Swim Spa/Tonal/Peloton
1010 out of 10 rating
Exceptional
(10 reviews)
Sleeping Giant Getaway w/ Swim Spa/Tonal/Peloton
Hamden, CT
8% off
Price is NZ$9,608
NZ$9,608
NZ$1,373 per night
includes taxes & fees
Image gallery for StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.
1010 out of 10 rating
Exceptional
(10 reviews)
StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.
Branford, CT
7% off
Price is NZ$2,808
NZ$2,808
NZ$401 per night
includes taxes & fees
Image gallery for Large Waterfront Modern Beach House
1010 out of 10 rating
Exceptional
(20 reviews)
Large Waterfront Modern Beach House
East Haven, CT
8% off
Price is NZ$9,988
NZ$9,988
NZ$1,427 per night
includes taxes & fees
Image gallery for Historic cottage 100 yards from private beach on private compound
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Historic cottage 100 yards from private beach on private compound
Branford, CT
19% off
Price is NZ$4,790
NZ$4,790
NZ$684 per night
includes taxes & fees
Image gallery for Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
1010 out of 10 rating
Exceptional
(49 reviews)
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
West Haven, CT
8% off
Price is NZ$7,996
NZ$7,996
NZ$1,142 per night
includes taxes & fees
Image gallery for BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
9.69.6 out of 10 rating
Exceptional
(10 reviews)
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Branford, CT
7% off
Price is NZ$3,249
NZ$3,249
NZ$464 per night
includes taxes & fees
Image gallery for Charming 3 Bedroom Beach Front Cottage with Fireplace
9.49.4 out of 10 rating
Exceptional
(28 reviews)
Charming 3 Bedroom Beach Front Cottage with Fireplace
Milford, CT
11% off
Price is NZ$5,889
NZ$5,889
NZ$841 per night
includes taxes & fees
Image gallery for Last minute cancellation for Labor Day Beautiful Ocean, botanical Garden.
1010 out of 10 rating
Exceptional
(15 reviews)
Last minute cancellation for Labor Day Beautiful Ocean, botanical Garden.
East Haven, CT
7% off
Price is NZ$2,858
NZ$2,858
NZ$408 per night
includes taxes & fees
Image gallery for 4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
1010 out of 10 rating
Exceptional
(33 reviews)
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
East Haven, CT
27% off
Price is NZ$8,407
NZ$8,407
NZ$1,201 per night
includes taxes & fees
Image gallery for Luxury private beach front property
1010 out of 10 rating
Exceptional
(11 reviews)
Luxury private beach front property
Milford, CT
12% off
Price is NZ$11,487
NZ$11,487
NZ$1,641 per night
includes taxes & fees
Image gallery for Ranch style living at its best with country garden & patio!
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Ranch style living at its best with country garden & patio!
North Haven, CT
8% off
Price is NZ$3,393
NZ$3,393
NZ$485 per night
includes taxes & fees
Image gallery for Beachside Retreat
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Beachside Retreat
West Haven, CT
7% off
Price is NZ$4,335
NZ$4,335
NZ$619 per night
includes taxes & fees
Image gallery for Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
West Haven, CT
10% off
Price is NZ$6,844
NZ$6,844
NZ$978 per night
includes taxes & fees
Image gallery for Ocean View cottage in Indian Neck. Super Host with 5-Star Rating
1010 out of 10 rating
Exceptional
(13 reviews)
Ocean View cottage in Indian Neck. Super Host with 5-Star Rating
Branford, CT
7% off
Price is NZ$3,276
NZ$3,276
NZ$468 per night
includes taxes & fees
Image gallery for Relax at Rudy's peaceful resting place...
1010 out of 10 rating
Exceptional
(5 reviews)
Relax at Rudy's peaceful resting place...
East Haven, CT
8% off
Price is NZ$3,454
NZ$3,454
NZ$493 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Wooster Square
Showing deals for: 31 Oct - 3 Nov
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
The current price is NZ$2,340
NZ$2,340
for 3 nights, 1 home
NZ$780 per night
includes taxes & fees
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Sleeps 22 · 11 bedrooms · 5+ bathrooms
The current price is NZ$37,982
NZ$37,982
for 3 nights, 1 home
NZ$12,661 per night
includes taxes & fees
Direct waterfront cottage on private sandy beach
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
The current price is NZ$2,039
NZ$2,039
for 3 nights, 1 cottage
NZ$680 per night
includes taxes & fees
Direct Waterfront Private Beach Escape
Sleeps 9 · 4 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
The current price is NZ$4,593
NZ$4,593
for 3 nights, 1 home
NZ$1,531 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Sleeps 6 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
The current price is NZ$4,085
NZ$4,085
for 3 nights, 1 home
NZ$1,362 per night
includes taxes & fees
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
Sleeps 10 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
The current price is NZ$5,208
NZ$5,208
for 3 nights, 1 home
NZ$1,736 per night
includes taxes & fees
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, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value