Holiday rentals near Waterski Connecticut
We found 889 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:7 Nov - 14 Nov
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 NZ$12,138
NZ$12,138
NZ$1,734 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 NZ$2,384
NZ$2,384
NZ$341 per night
includes taxes & fees
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 NZ$3,779
NZ$3,779
NZ$540 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$7,692
NZ$7,692
NZ$1,099 per night
includes taxes & fees
Image gallery for Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
Brookfield, CT
16% off
Price is NZ$22,036
NZ$22,036
NZ$3,148 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 NZ$4,245
NZ$4,245
NZ$606 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
52% off
Price is NZ$7,456
NZ$7,456
NZ$1,065 per night
includes taxes & fees
Image gallery for Candlewood Lake Perfection: Large and very private House, property and pool.
1010 out of 10 rating
Exceptional
(18 reviews)
Candlewood Lake Perfection: Large and very private House, property and pool.
Danbury, CT
8% off
Price is NZ$27,436
NZ$27,436
NZ$3,919 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
7% off
Price is NZ$13,030
NZ$13,030
NZ$1,861 per night
includes taxes & fees
Image gallery for Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!
Fairfield, CT
8% off
Price is NZ$20,814
NZ$20,814
NZ$2,973 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 NZ$2,702
NZ$2,702
NZ$386 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$9,544
NZ$9,544
NZ$1,363 per night
includes taxes & fees
Image gallery for Litchfield County Four Season Country Paradise
9.69.6 out of 10 rating
Exceptional
(46 reviews)
Litchfield County Four Season Country Paradise
Roxbury, CT
8% off
Price is NZ$14,040
NZ$14,040
NZ$2,006 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$9,635
NZ$9,635
NZ$1,376 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$7,936
NZ$7,936
NZ$1,134 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$12,937
NZ$12,937
NZ$1,848 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$9,016
NZ$9,016
NZ$1,288 per night
includes taxes & fees
Image gallery for Charming home, easy access - everything Branford. Super Host with 5-Star Rating
1010 out of 10 rating
Exceptional
(14 reviews)
Charming home, easy access - everything Branford. Super Host with 5-Star Rating
Branford, CT
7% off
Price is NZ$2,868
NZ$2,868
NZ$410 per night
includes taxes & fees
Image gallery for Stunning Waterfall View - 5 Bedroom
1010 out of 10 rating
Exceptional
(9 reviews)
Stunning Waterfall View - 5 Bedroom
Westport, CT
8% off
Price is NZ$10,032
NZ$10,032
NZ$1,433 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
(7 reviews)
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Bethel, CT
8% off
Price is NZ$3,062
NZ$3,062
NZ$437 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$8,989
NZ$8,989
NZ$1,284 per night
includes taxes & fees
Image gallery for Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
1010 out of 10 rating
Exceptional
(25 reviews)
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Danbury, CT
8% off
Price is NZ$6,710
NZ$6,710
NZ$959 per night
includes taxes & fees
Image gallery for Bohemian Beach Oasis- Welcome to paradise and your own private beach!
8.08.0 out of 10 rating
Very good
(6 reviews)
Bohemian Beach Oasis- Welcome to paradise and your own private beach!
Milford, CT
5% off
Price is NZ$4,545
NZ$4,545
NZ$649 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$5,380
NZ$5,380
NZ$769 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
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
136 reviews(136 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
Cute country cottage for getaway stay
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
194 reviews(194 reviews)
Top rated rentals - Waterski Connecticut
Beautiful home away from home
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Clean and tidy, close to amenities, friendly responsive hosts, would definitely stay again.
Cheryl A.
Stayed Apr 2025
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