Photo by Tiffany Zhou
Holiday rentals near Woolsey Hall
We found 779 holiday rentals — enter your dates for availability
Take a look at private holiday rentals near Woolsey Hall that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for spending time at your holiday home, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Woolsey Hall
Showing deals for:18 Jul - 25 Jul
Image gallery for Vrbo Property
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Vrbo Property
Bridgeport, CT
8% off
Price is NZ$6,991
NZ$6,991
NZ$999 per night
includes taxes & fees
Image gallery for Entire home PRIVATE BEACH live like a celebrity! Saturday-Saturday ONLY
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Entire home PRIVATE BEACH live like a celebrity! Saturday-Saturday ONLY
Milford, CT
8% off
Price is NZ$10,197
NZ$10,197
NZ$1,457 per night
includes taxes & fees
Image gallery for Luxury Beach Oasis with Amazing Panoramic Ocean Views
1010 out of 10 rating
Exceptional
(6 reviews)
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Milford, CT
8% off
Price is NZ$16,953
NZ$16,953
NZ$2,422 per night
includes taxes & fees
Image gallery for Enjoy the serenity of the countryside at Pleasant Valley Trails - Home & Acres
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Enjoy the serenity of the countryside at Pleasant Valley Trails - Home & Acres
Shelton, CT
10% off
Price is NZ$1,858
NZ$1,858
NZ$265 per night
includes taxes & fees
Image gallery for Private Home - Pool and Close to CT Shoreline Beaches
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Private Home - Pool and Close to CT Shoreline Beaches
North Branford, CT
16% off
Price is NZ$9,856
NZ$9,856
NZ$1,408 per night
includes taxes & fees
Image gallery for Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!
1010 out of 10 rating
Exceptional
(86 reviews)
Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!
Trumbull, CT
5% off
Price is NZ$5,591
NZ$5,591
NZ$799 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$11,514
NZ$11,514
NZ$1,645 per night
includes taxes & fees
Image gallery for Amazing 11 Bedroom 15 Bathroom Mansion Close to Beaches
1010 out of 10 rating
Exceptional
(5 reviews)
Amazing 11 Bedroom 15 Bathroom Mansion Close to Beaches
Killingworth, CT
8% off
Price is NZ$37,958
NZ$37,958
NZ$5,423 per night
includes taxes & fees
Image gallery for Direct Waterfront Private Beach Escape
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Direct Waterfront Private Beach Escape
East Haven, CT
8% off
Price is NZ$13,005
NZ$13,005
NZ$1,858 per night
includes taxes & fees
Image gallery for 1930s Waterfront Cottage on Tuttle's Point
9.89.8 out of 10 rating
Exceptional
(28 reviews)
1930s Waterfront Cottage on Tuttle's Point
Guilford, CT
7% off
Price is NZ$7,750
NZ$7,750
NZ$1,107 per night
includes taxes & fees
Image gallery for Fun Lake Front Cottage!
9.89.8 out of 10 rating
Exceptional
(89 reviews)
Fun Lake Front Cottage!
Middlefield, CT
7% off
Price is NZ$3,067
NZ$3,067
NZ$438 per night
includes taxes & fees
Image gallery for Winchester - Your Home Away from Home
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Winchester - Your Home Away from Home
New Haven, CT
8% off
Price is NZ$3,610
NZ$3,610
NZ$516 per night
includes taxes & fees
Image gallery for Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
1010 out of 10 rating
Exceptional
(26 reviews)
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Fairfield, CT
8% off
Price is NZ$6,704
NZ$6,704
NZ$958 per night
includes taxes & fees
Image gallery for Newly renovated w/ Brand new kitchen and updated living room with more windows!
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Newly renovated w/ Brand new kitchen and updated living room with more windows!
Guilford, CT
8% off
Price is NZ$7,864
NZ$7,864
NZ$1,123 per night
includes taxes & fees
Image gallery for Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
1010 out of 10 rating
Exceptional
(128 reviews)
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Branford, CT
8% off
Price is NZ$6,016
NZ$6,016
NZ$859 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$9,544
NZ$9,544
NZ$1,363 per night
includes taxes & fees
Image gallery for 4 bedroom - steps to sandy beach in perfect location!
1010 out of 10 rating
Exceptional
(20 reviews)
4 bedroom - steps to sandy beach in perfect location!
Madison, CT
8% off
Price is NZ$10,186
NZ$10,186
NZ$1,455 per night
includes taxes & fees
Image gallery for 🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass
9.29.2 out of 10 rating
Wonderful
(88 reviews)
🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass
Guilford, CT
8% off
Price is NZ$6,823
NZ$6,823
NZ$975 per night
includes taxes & fees
Image gallery for Historic Whitneyville Cottage
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Historic Whitneyville Cottage
Hamden, CT
7% off
Price is NZ$2,349
NZ$2,349
NZ$336 per night
includes taxes & fees
Image gallery for Lake Front Home.....
9.89.8 out of 10 rating
Exceptional
(89 reviews)
Lake Front Home.....
Middlefield, CT
8% off
Price is NZ$4,706
NZ$4,706
NZ$672 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$3,393
NZ$3,393
NZ$485 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
(30 reviews)
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
East Haven, CT
17% off
Price is NZ$10,014
NZ$10,014
NZ$1,431 per night
includes taxes & fees
Image gallery for Cheerful 4 bedrooms residential house.
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Cheerful 4 bedrooms residential house.
Bridgeport, CT
8% off
Price is NZ$4,287
NZ$4,287
NZ$612 per night
includes taxes & fees
Image gallery for Centric property close to all the great things in the city
8.28.2 out of 10 rating
Very good
(10 reviews)
Centric property close to all the great things in the city
Bridgeport, CT
12% off
Price is NZ$2,311
NZ$2,311
NZ$330 per night
includes taxes & fees
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Find the best place to stay - Woolsey Hall
The Queen of the Thimble Islands
Sleeps 15 · 8 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Cute country cottage for getaway stay
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
180 reviews(180 reviews)
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Sleeps 22 · 11 bedrooms · 5+ bathrooms
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
128 reviews(128 reviews)
Beautiful fully equipped CT Walnut Beach cottage w/SUP & Kayak 4 min from beach!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
35 reviews(35 reviews)
Beautiful 4BR Beach House with Private Beach Access.
Sleeps 8 · 4 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
70 reviews(70 reviews)
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