Holiday rentals near Ski Sundown
We found 361 holiday rentals — enter your dates for availability
Take a look at private holiday rentals near Ski Sundown that provide the perfect home base for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for spending time at your holiday home, which might include air conditioning and a pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Ski Sundown
Showing deals for:19 Sept - 26 Sept
Image gallery for Sweetbrier Farm -- Gorgeous Views, Beautiful Home
1010 out of 10 rating
Exceptional
(28 reviews)
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield, CT
12% off
Price is AU$8,425
AU$8,425
AU$1,204 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is AU$2,899
AU$2,899
AU$414 per night
includes taxes & fees
Image gallery for ISLAND WATERFRONT Sleeps up to 8
9.09.0 out of 10 rating
Wonderful
(72 reviews)
ISLAND WATERFRONT Sleeps up to 8
Southwick, MA
8% off
Price is AU$3,118
AU$3,118
AU$445 per night
includes taxes & fees
Image gallery for Cozy Ranch - Conveniently Located - Entire Home Available for Use!
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Cozy Ranch - Conveniently Located - Entire Home Available for Use!
East Granby, CT
8% off
Price is AU$3,648
AU$3,648
AU$521 per night
includes taxes & fees
Image gallery for Cozy Lakefront Bungalow w firepit/dock/kayaks
1010 out of 10 rating
Exceptional
(26 reviews)
Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth, CT
8% off
Price is AU$6,203
AU$6,203
AU$886 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(33 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is AU$4,993
AU$4,993
AU$713 per night
includes taxes & fees
Image gallery for Charming Historic Owl House in Old Wethersfield
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Charming Historic Owl House in Old Wethersfield
Wethersfield, CT
8% off
Price is AU$8,658
AU$8,658
AU$1,237 per night
includes taxes & fees
Image gallery for Hilltop House
1010 out of 10 rating
Exceptional
(5 reviews)
Hilltop House
Bantam, CT
8% off
Price is AU$6,824
AU$6,824
AU$975 per night
includes taxes & fees
Image gallery for Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
1010 out of 10 rating
Exceptional
(56 reviews)
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Canton, CT
8% off
Price is AU$3,818
AU$3,818
AU$545 per night
includes taxes & fees
Image gallery for A “Wow” Experience everywhere there is something to stimulate your mind Interest
9.69.6 out of 10 rating
Exceptional
(5 reviews)
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Windsor, CT
8% off
Price is AU$3,917
AU$3,917
AU$560 per night
includes taxes & fees
Image gallery for Direct Waterfront with Private Beach - Entire Home
1010 out of 10 rating
Exceptional
(31 reviews)
Direct Waterfront with Private Beach - Entire Home
Harwinton, CT
8% off
Price is AU$4,222
AU$4,222
AU$603 per night
includes taxes & fees
Image gallery for Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
1010 out of 10 rating
Exceptional
(19 reviews)
Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
Harwinton, CT
7% off
Price is AU$2,955
AU$2,955
AU$422 per night
includes taxes & fees
Image gallery for Lakefront Tranquility/Fishermans Delight
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Lakefront Tranquility/Fishermans Delight
New Hartford, CT
8% off
Price is AU$3,520
AU$3,520
AU$503 per night
includes taxes & fees
Image gallery for Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.29.2 out of 10 rating
Wonderful
(41 reviews)
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Winsted, CT
8% off
Price is AU$1,628
AU$1,628
AU$233 per night
includes taxes & fees
Image gallery for Mountaintop Horse Farm with Heated Pool
1010 out of 10 rating
Exceptional
(25 reviews)
Mountaintop Horse Farm with Heated Pool
Bloomfield, CT
8% off
Price is AU$3,520
AU$3,520
AU$503 per night
includes taxes & fees
Image gallery for Cozy BoHo pet & family friendly near downtown & hospitals
8.68.6 out of 10 rating
Excellent
(8 reviews)
Cozy BoHo pet & family friendly near downtown & hospitals
Hartford, CT
13% off
Price is AU$1,479
AU$1,479
AU$211 per night
includes taxes & fees
Image gallery for Peaceful Meadow Retreat
1010 out of 10 rating
Exceptional
(9 reviews)
Peaceful Meadow Retreat
Granby, CT
12% off
Price is AU$1,705
AU$1,705
AU$244 per night
includes taxes & fees
Image gallery for Romantic weekend getaway for two! featuring a fireplace and hot tub,
9.89.8 out of 10 rating
Exceptional
(57 reviews)
Romantic weekend getaway for two! featuring a fireplace and hot tub,
Sandisfield, MA
8% off
Price is AU$2,652
AU$2,652
AU$379 per night
includes taxes & fees
Image gallery for The Overlook near South Farms in Litchfield County is Hospitality, integrated.
9.29.2 out of 10 rating
Wonderful
(5 reviews)
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris, CT
8% off
Price is AU$2,641
AU$2,641
AU$377 per night
includes taxes & fees
Image gallery for Charming 2-bedroom house centrally located in Bristol
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Charming 2-bedroom house centrally located in Bristol
Bristol, CT
8% off
Price is AU$1,862
AU$1,862
AU$266 per night
includes taxes & fees
Image gallery for Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is AU$2,280
AU$2,280
AU$326 per night
includes taxes & fees
Image gallery for Beautiful retreat in a lake community to the enjoy the summer season.
1010 out of 10 rating
Exceptional
(39 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
9% off
Price is AU$2,589
AU$2,589
AU$370 per night
includes taxes & fees
Image gallery for Linny’s Lake Retreat, Family-Friendly & Dock Access
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Linny’s Lake Retreat, Family-Friendly & Dock Access
Southwick, CT
8% off
Price is AU$2,966
AU$2,966
AU$424 per night
includes taxes & fees
Image gallery for comfortable home away from home
8.08.0 out of 10 rating
Very good
(9 reviews)
comfortable home away from home
East Hartford, CT
7% off
Price is AU$2,320
AU$2,320
AU$331 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
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Chalet
Find the best place to stay - Ski Sundown
Lake Congamond Cozy Stylish Comfortable House
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Tolland Cabin w/ Private Hot Tub & Grill!
Sleeps 5 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Lakefront Granby Escape w/ Private Dock & Kayaks!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
11 reviews(11 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
Top rated rentals - Ski Sundown
Lovely
1010 out of 10
Exceptionalexceptional
27 reviews(27 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