Holiday rentals near Waterski Connecticut
We found 892 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:21 Nov - 28 Nov
Image gallery for Lakefront Home, Close to Mt Southington!
1010 out of 10 rating
Exceptional
(19 reviews)
Lakefront Home, Close to Mt Southington!
Wolcott, CT
7% off
Price is AU$3,828
AU$3,828
AU$547 per night
includes taxes & fees
Image gallery for Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
1010 out of 10 rating
Exceptional
(20 reviews)
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Danbury, CT
8% off
Price is AU$10,868
AU$10,868
AU$1,553 per night
includes taxes & fees
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 AU$2,137
AU$2,137
AU$305 per night
includes taxes & fees
Image gallery for 100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ
9.89.8 out of 10 rating
Exceptional
(6 reviews)
100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ
Roxbury, CT
51% off
Price is AU$8,460
AU$8,460
AU$1,209 per night
includes taxes & fees
Image gallery for Renovated Milford Beach home by Charles Island/Silver Sands Pk
1010 out of 10 rating
Exceptional
(6 reviews)
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Milford, CT
8% off
Price is AU$3,867
AU$3,867
AU$552 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 AU$7,279
AU$7,279
AU$1,040 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 AU$4,668
AU$4,668
AU$667 per night
includes taxes & fees
Image gallery for Beautiful Beachfront Cottage Leading Directly To Your Own Sandy Beach
1010 out of 10 rating
Exceptional
(40 reviews)
Beautiful Beachfront Cottage Leading Directly To Your Own Sandy Beach
Milford, CT
12% off
Price is AU$5,538
AU$5,538
AU$791 per night
includes taxes & fees
Image gallery for 3br\2ba: Quiet and Cozy Getaway in Milford
1010 out of 10 rating
Exceptional
(6 reviews)
3br\2ba: Quiet and Cozy Getaway in Milford
Milford, CT
24% off
Price is AU$2,598
AU$2,598
AU$371 per night
includes taxes & fees
Image gallery for Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
1010 out of 10 rating
Exceptional
(26 reviews)
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Danbury, CT
8% off
Price is AU$7,325
AU$7,325
AU$1,046 per night
includes taxes & fees
Image gallery for BEST TOWN ROXBURY! PoshPadsCT "PAINTER - POOL" 1.5Hrs NYC, Mint, Ski, Fires, BBQ
9.49.4 out of 10 rating
Exceptional
(8 reviews)
BEST TOWN ROXBURY! PoshPadsCT "PAINTER - POOL" 1.5Hrs NYC, Mint, Ski, Fires, BBQ
Roxbury, CT
35% off
Price is AU$10,356
AU$10,356
AU$1,479 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 AU$11,633
AU$11,633
AU$1,662 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 AU$4,834
AU$4,834
AU$691 per night
includes taxes & fees
Image gallery for Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
1010 out of 10 rating
Exceptional
(8 reviews)
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Bethel, CT
8% off
Price is AU$2,932
AU$2,932
AU$419 per night
includes taxes & fees
Image gallery for New England Beach House ~ Just Steps To The Beach ~ Perfect Getaway!
9.69.6 out of 10 rating
Exceptional
(27 reviews)
New England Beach House ~ Just Steps To The Beach ~ Perfect Getaway!
Milford, CT
7% off
Price is AU$2,707
AU$2,707
AU$387 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 AU$8,947
AU$8,947
AU$1,278 per night
includes taxes & fees
Image gallery for Historic Designer City Getaway
1010 out of 10 rating
Exceptional
(11 reviews)
Historic Designer City Getaway
Easton, CT
8% off
Price is AU$12,940
AU$12,940
AU$1,849 per night
includes taxes & fees
Image gallery for Direct Waterfront "The Palms" Beach House
1010 out of 10 rating
Exceptional
(9 reviews)
Direct Waterfront "The Palms" Beach House
Milford, CT
8% off
Price is AU$6,707
AU$6,707
AU$958 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
8% off
Price is AU$3,366
AU$3,366
AU$481 per night
includes taxes & fees
Image gallery for Charming 3-bedroom house with WiFi, AC in serene Fairfield
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Fairfield, CT
7% off
Price is AU$2,488
AU$2,488
AU$355 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 AU$9,056
AU$9,056
AU$1,294 per night
includes taxes & fees
Image gallery for BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
1010 out of 10 rating
Exceptional
(37 reviews)
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Milford, CT
8% off
Price is AU$1,892
AU$1,892
AU$270 per night
includes taxes & fees
Image gallery for Charming Beach Home-Steps To Sandy Beach
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Charming Beach Home-Steps To Sandy Beach
Milford, CT
8% off
Price is AU$3,662
AU$3,662
AU$523 per night
includes taxes & fees
Image gallery for Hat Shop House: Charming Retreat in the Heart of New England. Family friendly.
1010 out of 10 rating
Exceptional
(7 reviews)
Hat Shop House: Charming Retreat in the Heart of New England. Family friendly.
Bridgewater, CT
8% off
Price is AU$7,181
AU$7,181
AU$1,026 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Waterski Connecticut
The Queen of the Thimble Islands
Sleeps 15 · 8 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
139 reviews(139 reviews)
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)
CT Private Home on Belden Island
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Sleeps 22 · 11 bedrooms · 5+ bathrooms
Direct Waterfront Private Beach Escape
Sleeps 9 · 4 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
16 reviews(16 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