Holiday rentals near Waterski Connecticut
We found 905 holiday rentals — enter your dates for availability
Select the perfect holiday rental that's close to Waterski Connecticut. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a pool. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Waterski Connecticut
Showing deals for:19 Sept - 26 Sept
Image gallery for A Secluded Modern Getaway
1010 out of 10 rating
Exceptional
(7 reviews)
A Secluded Modern Getaway
Redding, CT
8% off
Price is NZ$12,369
NZ$12,369
NZ$1,767 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$9,701
NZ$9,701
NZ$1,386 per night
includes taxes & fees
Image gallery for Litchfield County Four Season Country Paradise
9.69.6 out of 10 rating
Exceptional
(40 reviews)
Litchfield County Four Season Country Paradise
Roxbury, CT
8% off
Price is NZ$13,915
NZ$13,915
NZ$1,988 per night
includes taxes & fees
Image gallery for Waterfront home- Sleeps 10 - private beach-epic pool
1010 out of 10 rating
Exceptional
(25 reviews)
Waterfront home- Sleeps 10 - private beach-epic pool
Branford, CT
5% off
Price is NZ$24,508
NZ$24,508
NZ$3,501 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$9,548
NZ$9,548
NZ$1,364 per night
includes taxes & fees
Image gallery for 6-Acre Luxurious Country Home with Goddess Point Lookout
1010 out of 10 rating
Exceptional
(9 reviews)
6-Acre Luxurious Country Home with Goddess Point Lookout
Woodbury, CT
8% off
Price is NZ$9,690
NZ$9,690
NZ$1,384 per night
includes taxes & fees
Image gallery for On the Water Spacious Comfortable Historic Home
1010 out of 10 rating
Exceptional
(5 reviews)
On the Water Spacious Comfortable Historic Home
West Haven, CT
8% off
Price is NZ$9,006
NZ$9,006
NZ$1,287 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
7% off
Price is NZ$4,236
NZ$4,236
NZ$605 per night
includes taxes & fees
Image gallery for BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Branford, CT
8% off
Price is NZ$3,997
NZ$3,997
NZ$571 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$8,701
NZ$8,701
NZ$1,243 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$11,502
NZ$11,502
NZ$1,643 per night
includes taxes & fees
Image gallery for Lakeside luxury: beautiful, relaxing 4 bedroom home
1010 out of 10 rating
Exceptional
(22 reviews)
Lakeside luxury: beautiful, relaxing 4 bedroom home
Trumbull, CT
8% off
Price is NZ$6,306
NZ$6,306
NZ$901 per night
includes taxes & fees
Image gallery for Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
1010 out of 10 rating
Exceptional
(9 reviews)
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Weston, CT
8% off
Price is NZ$4,902
NZ$4,902
NZ$700 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$11,229
NZ$11,229
NZ$1,604 per night
includes taxes & fees
Image gallery for Direct Waterfront Private Beach Escape
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Direct Waterfront Private Beach Escape
East Haven, CT
15% off
Price is NZ$10,031
NZ$10,031
NZ$1,433 per night
includes taxes & fees
Image gallery for Amazing Lake House
1010 out of 10 rating
Exceptional
(31 reviews)
Amazing Lake House
Brookfield, CT
8% off
Price is NZ$5,594
NZ$5,594
NZ$799 per night
includes taxes & fees
Image gallery for Charming 3 Bedroom Beach Front Cottage with Fireplace
9.49.4 out of 10 rating
Exceptional
(27 reviews)
Charming 3 Bedroom Beach Front Cottage with Fireplace
Milford, CT
8% off
Price is NZ$8,064
NZ$8,064
NZ$1,152 per night
includes taxes & fees
Image gallery for Direct Lakefront Home on Lake Lillinonah with Elevator Access
1010 out of 10 rating
Exceptional
(29 reviews)
Direct Lakefront Home on Lake Lillinonah with Elevator Access
Brookfield, CT
8% off
Price is NZ$8,670
NZ$8,670
NZ$1,239 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$4,730
NZ$4,730
NZ$676 per night
includes taxes & fees
Image gallery for Historic Designer City Getaway
1010 out of 10 rating
Exceptional
(9 reviews)
Historic Designer City Getaway
Easton, CT
7% off
Price is NZ$12,899
NZ$12,899
NZ$1,843 per night
includes taxes & fees
Image gallery for A country guest house just 21-32 minutes Bridgeport or New Haven Universities.
9.49.4 out of 10 rating
Exceptional
(20 reviews)
A country guest house just 21-32 minutes Bridgeport or New Haven Universities.
Shelton, CT
8% off
Price is NZ$1,870
NZ$1,870
NZ$267 per night
includes taxes & fees
Image gallery for Beachside Retreat
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Beachside Retreat
West Haven, CT
7% off
Price is NZ$4,336
NZ$4,336
NZ$619 per night
includes taxes & fees
Image gallery for 3br\2ba: Quiet and Cozy Getaway in Milford
1010 out of 10 rating
Exceptional
(5 reviews)
3br\2ba: Quiet and Cozy Getaway in Milford
Milford, CT
24% off
Price is NZ$2,660
NZ$2,660
NZ$380 per night
includes taxes & fees
Image gallery for Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
1010 out of 10 rating
Exceptional
(5 reviews)
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Bethlehem, CT
7% off
Price is NZ$4,643
NZ$4,643
NZ$663 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Waterski Connecticut
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
131 reviews(131 reviews)
The Queen of the Thimble Islands
Sleeps 15 · 8 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Cute country cottage for getaway stay
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
188 reviews(188 reviews)
CT Private Home on Belden Island
Sleeps 8 · 4 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
1 review(1 review)
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
Sleeps 12 · 6 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 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