Holiday rentals near Ski Sundown
We found 358 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:31 Oct - 7 Nov
Image gallery for County Seat Colonial
1010 out of 10 rating
Exceptional
(11 reviews)
County Seat Colonial
Litchfield, CT
8% off
Price is AU$4,635
AU$4,635
AU$662 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(35 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is AU$6,197
AU$6,197
AU$885 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
(40 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
9% off
Price is AU$2,588
AU$2,588
AU$370 per night
includes taxes & fees
Image gallery for Charming 1870 cape cottage in Litchfield
1010 out of 10 rating
Exceptional
(52 reviews)
Charming 1870 cape cottage in Litchfield
Litchfield, CT
8% off
Price is AU$3,024
AU$3,024
AU$432 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
(18 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is AU$2,467
AU$2,467
AU$352 per night
includes taxes & fees
Image gallery for Mountaintop Horse Farm with Heated Pool
1010 out of 10 rating
Exceptional
(31 reviews)
Mountaintop Horse Farm with Heated Pool
Bloomfield, CT
8% off
Price is AU$3,517
AU$3,517
AU$502 per night
includes taxes & fees
Image gallery for Direct Waterfront with Private Beach - Entire Home
1010 out of 10 rating
Exceptional
(33 reviews)
Direct Waterfront with Private Beach - Entire Home
Harwinton, CT
8% off
Price is AU$3,441
AU$3,441
AU$492 per night
includes taxes & fees
Image gallery for A “Wow” Experience everywhere there is something to stimulate your mind Interest
9.29.2 out of 10 rating
Wonderful
(7 reviews)
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Windsor, CT
8% off
Price is AU$3,915
AU$3,915
AU$559 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$2,292
AU$2,292
AU$327 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(17 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is AU$2,897
AU$2,897
AU$414 per night
includes taxes & fees
Image gallery for Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Avon, CT
8% off
Price is AU$3,629
AU$3,629
AU$518 per night
includes taxes & fees
Image gallery for Stylish & Luxurious 3 BDR Home with Play Station
9.29.2 out of 10 rating
Wonderful
(15 reviews)
Stylish & Luxurious 3 BDR Home with Play Station
Bristol, CT
7% off
Price is AU$1,883
AU$1,883
AU$269 per night
includes taxes & fees
Image gallery for AUGUST 2025 AVAILABLE for 15K 4BR 3BA @ Woodridge Lake with Pool, Tennis, Gym
1010 out of 10 rating
Exceptional
(22 reviews)
AUGUST 2025 AVAILABLE for 15K 4BR 3BA @ Woodridge Lake with Pool, Tennis, Gym
Goshen, CT
16% off
Price is AU$7,005
AU$7,005
AU$1,001 per night
includes taxes & fees
Image gallery for Charming apartment 7 minute walk to downtown
1010 out of 10 rating
Exceptional
(13 reviews)
Charming apartment 7 minute walk to downtown
Torrington, CT
8% off
Price is AU$2,068
AU$2,068
AU$295 per night
includes taxes & fees
Image gallery for Cherrybrook Hideaway - Book now for autumn colors!
1010 out of 10 rating
Exceptional
(14 reviews)
Cherrybrook Hideaway - Book now for autumn colors!
Canton, CT
8% off
Price is AU$3,856
AU$3,856
AU$551 per night
includes taxes & fees
Image gallery for Cozy Lakefront Bungalow w firepit/dock/kayaks
1010 out of 10 rating
Exceptional
(29 reviews)
Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth, CT
8% off
Price is AU$6,197
AU$6,197
AU$885 per night
includes taxes & fees
Image gallery for Peaceful Meadow Retreat
1010 out of 10 rating
Exceptional
(9 reviews)
Peaceful Meadow Retreat
Granby, CT
10% off
Price is AU$1,603
AU$1,603
AU$229 per night
includes taxes & fees
Image gallery for Riverside Farm
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Riverside Farm
Canton, CT
8% off
Price is AU$5,028
AU$5,028
AU$718 per night
includes taxes & fees
Image gallery for NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.49.4 out of 10 rating
Exceptional
(23 reviews)
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Windsor, CT
7% off
Price is AU$1,822
AU$1,822
AU$260 per night
includes taxes & fees
Image gallery for Cozy BoHo pet & family friendly near downtown & hospitals
8.28.2 out of 10 rating
Very good
(10 reviews)
Cozy BoHo pet & family friendly near downtown & hospitals
Hartford, CT
13% off
Price is AU$1,343
AU$1,343
AU$192 per night
includes taxes & fees
Image gallery for Linny’s Lake Retreat, Family-Friendly & Dock Access
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Linny’s Lake Retreat, Family-Friendly & Dock Access
Southwick, CT
8% off
Price is AU$2,735
AU$2,735
AU$391 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
(42 reviews)
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Winsted, CT
8% off
Price is AU$1,604
AU$1,604
AU$229 per night
includes taxes & fees
Image gallery for Summer Lake Escape - Hot Tub • Game Room • 1-Min Walk to Kayaking & Swimming
1010 out of 10 rating
Exceptional
(5 reviews)
Summer Lake Escape - Hot Tub • Game Room • 1-Min Walk to Kayaking & Swimming
Terryville, CT
22% off
Price is AU$2,487
AU$2,487
AU$355 per night
includes taxes & fees
Image gallery for Charming 2-bedroom house centrally located in Bristol
9.69.6 out of 10 rating
Exceptional
(12 reviews)
Charming 2-bedroom house centrally located in Bristol
Bristol, CT
8% off
Price is AU$1,830
AU$1,830
AU$261 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Ski Sundown
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Sleeps 10 · 5 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
CT Gate House Goshen CT, Gate House Goshen CT
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Beautiful Home w/ Hot Tub in a Private Lake Community
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!
Sleeps 9 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Litchfield Hills Lakefront Home! Amazing location, views and sunsets
Sleeps 10 · 5 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
Top rated rentals - Ski Sundown
Lovely
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Lovely home, lovely area, very comfy bed, very welcoming hosts.
Jennifer C.
Stayed May 2024
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