Holiday rentals near Woodbury Ski Area
We found 454 holiday rentals — enter your dates for availability
Take a look at private holiday rentals close to Woodbury Ski Area that can be your home away from home. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include Wi-Fi and a hot tub. You're sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Woodbury Ski Area
Showing deals for:26 Sept - 3 Oct
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
17% off
Price is AU$18,067
AU$18,067
AU$2,581 per night
includes taxes & fees
Image gallery for Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
1010 out of 10 rating
Exceptional
(9 reviews)
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Watertown, CT
8% off
Price is AU$12,764
AU$12,764
AU$1,823 per night
includes taxes & fees
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$8,976
AU$8,976
AU$1,282 per night
includes taxes & fees
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 AU$11,583
AU$11,583
AU$1,655 per night
includes taxes & fees
Image gallery for Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball
1010 out of 10 rating
Exceptional
(5 reviews)
Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball
New Fairfield, CT
8% off
Price is AU$4,665
AU$4,665
AU$666 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 AU$12,616
AU$12,616
AU$1,802 per night
includes taxes & fees
Image gallery for Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
1010 out of 10 rating
Exceptional
(13 reviews)
Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
Bethlehem, CT
8% off
Price is AU$7,083
AU$7,083
AU$1,012 per night
includes taxes & fees
Image gallery for Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
9.69.6 out of 10 rating
Exceptional
(65 reviews)
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
Bethlehem, CT
8% off
Price is AU$2,777
AU$2,777
AU$397 per night
includes taxes & fees
Image gallery for Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Cornwall Bridge, CT
8% off
Price is AU$9,142
AU$9,142
AU$1,306 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
(6 reviews)
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Bethel, CT
8% off
Price is AU$2,821
AU$2,821
AU$403 per night
includes taxes & fees
Image gallery for Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!
1010 out of 10 rating
Exceptional
(11 reviews)
Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!
Bethlehem, CT
7% off
Price is AU$4,097
AU$4,097
AU$585 per night
includes taxes & fees
Image gallery for Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
Brewster, NY
8% off
Price is AU$13,350
AU$13,350
AU$1,907 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$3,966
AU$3,966
AU$567 per night
includes taxes & fees
Image gallery for Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
1010 out of 10 rating
Exceptional
(5 reviews)
Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
New Milford, CT
12% off
Price is AU$7,170
AU$7,170
AU$1,024 per night
includes taxes & fees
Image gallery for 4BR 3BA @ Woodridge Lake with Pool, Tennis, Beaches, Gym, Events, AC, WiFi
1010 out of 10 rating
Exceptional
(22 reviews)
4BR 3BA @ Woodridge Lake with Pool, Tennis, Beaches, Gym, Events, AC, WiFi
Goshen, CT
10% off
Price is AU$7,546
AU$7,546
AU$1,078 per night
includes taxes & fees
Image gallery for Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!
1010 out of 10 rating
Exceptional
(26 reviews)
Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!
Roxbury, CT
11% off
Price is AU$2,050
AU$2,050
AU$293 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$6,182
AU$6,182
AU$883 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$4,976
AU$4,976
AU$711 per night
includes taxes & fees
Image gallery for Candlewood Cabin - with Private Waterfront
1010 out of 10 rating
Exceptional
(8 reviews)
Candlewood Cabin - with Private Waterfront
New Fairfield, CT
8% off
Price is AU$4,015
AU$4,015
AU$574 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 AU$7,844
AU$7,844
AU$1,121 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 Amazing Lake House
1010 out of 10 rating
Exceptional
(31 reviews)
Amazing Lake House
Brookfield, CT
8% off
Price is AU$4,987
AU$4,987
AU$712 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
8% off
Price is AU$4,218
AU$4,218
AU$603 per night
includes taxes & fees
Image gallery for Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
1010 out of 10 rating
Exceptional
(7 reviews)
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Sherman, CT
8% off
Price is AU$5,771
AU$5,771
AU$824 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Woodbury Ski Area
Cozy cute Relaxing home
Sleeps 3 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Have a quiet weekend retreat at my recently renovated riverside bungalow
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 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