Holiday rentals near Woodbury Ski Area
We found 462 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:3 Oct - 10 Oct
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 NZ$8,983
NZ$8,983
NZ$1,283 per night
includes taxes & fees
Image gallery for Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
1010 out of 10 rating
Exceptional
(5 reviews)
Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
New Fairfield, CT
8% off
Price is NZ$25,494
NZ$25,494
NZ$3,642 per night
includes taxes & fees
Image gallery for Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
1010 out of 10 rating
Exceptional
(79 reviews)
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
New Fairfield, CT
11% off
Price is NZ$20,595
NZ$20,595
NZ$2,942 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 NZ$12,625
NZ$12,625
NZ$1,804 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
7% off
Price is NZ$14,229
NZ$14,229
NZ$2,033 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
(66 reviews)
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
Bethlehem, CT
8% off
Price is NZ$2,989
NZ$2,989
NZ$427 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 NZ$5,086
NZ$5,086
NZ$727 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
(14 reviews)
Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
Bethlehem, CT
8% off
Price is NZ$7,756
NZ$7,756
NZ$1,108 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 NZ$4,406
NZ$4,406
NZ$629 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 NZ$9,029
NZ$9,029
NZ$1,290 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 NZ$18,749
NZ$18,749
NZ$2,678 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 NZ$3,699
NZ$3,699
NZ$528 per night
includes taxes & fees
Image gallery for Charming 1870 cape cottage in Litchfield
1010 out of 10 rating
Exceptional
(51 reviews)
Charming 1870 cape cottage in Litchfield
Litchfield, CT
8% off
Price is NZ$3,289
NZ$3,289
NZ$470 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 NZ$7,849
NZ$7,849
NZ$1,121 per night
includes taxes & fees
Image gallery for Modern Barn, NEW Luxurious Home
1010 out of 10 rating
Exceptional
(35 reviews)
Modern Barn, NEW Luxurious Home
New Preston, CT
8% off
Price is NZ$12,024
NZ$12,024
NZ$1,718 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 NZ$6,634
NZ$6,634
NZ$948 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 NZ$5,008
NZ$5,008
NZ$715 per night
includes taxes & fees
Image gallery for Beautiful Cottage and Waterfront Access
9.89.8 out of 10 rating
Exceptional
(104 reviews)
Beautiful Cottage and Waterfront Access
New Preston, CT
8% off
Price is NZ$3,553
NZ$3,553
NZ$508 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 NZ$5,348
NZ$5,348
NZ$764 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 NZ$8,584
NZ$8,584
NZ$1,226 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 NZ$9,747
NZ$9,747
NZ$1,392 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 NZ$4,900
NZ$4,900
NZ$700 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 NZ$6,201
NZ$6,201
NZ$886 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 NZ$2,342
NZ$2,342
NZ$335 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Woodbury Ski Area
Magnificent Lake View
Sleeps 6 · 2 bedrooms · 1+ bathroom
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Sleeps 20 · 6 bedrooms · 3 bathrooms
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Sleeps 8 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
14 reviews(14 reviews)
Candlewood Lake Retreat
Sleeps 6 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
91 reviews(91 reviews)
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
23 reviews(23 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