Holiday rentals near Woodbury Ski Area
We found 468 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:15 Aug - 22 Aug
Image gallery for Sweetbrier Farm -- Gorgeous Views, Beautiful Home
1010 out of 10 rating
Exceptional
(27 reviews)
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield, CT
12% off
Price is NZ$9,747
NZ$9,747
NZ$1,392 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
12% off
Price is NZ$20,410
NZ$20,410
NZ$2,916 per night
includes taxes & fees
Image gallery for Bantam Beauty - Surrounded By Nature!
1010 out of 10 rating
Exceptional
(11 reviews)
Bantam Beauty - Surrounded By Nature!
Bantam, CT
9% off
Price is NZ$9,996
NZ$9,996
NZ$1,428 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 NZ$17,084
NZ$17,084
NZ$2,441 per night
includes taxes & fees
Image gallery for Charming 3BR Hilltop House, Newly Remodeled with Arcade
1010 out of 10 rating
Exceptional
(19 reviews)
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Terryville, CT
7% off
Price is NZ$2,744
NZ$2,744
NZ$392 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$5,747
NZ$5,747
NZ$821 per night
includes taxes & fees
Image gallery for 1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
1010 out of 10 rating
Exceptional
(11 reviews)
1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
Litchfield, CT
25% off
Price is NZ$5,437
NZ$5,437
NZ$777 per night
includes taxes & fees
Image gallery for 6-Acre Luxurious Country Home with Goddess Point Lookout
1010 out of 10 rating
Exceptional
(8 reviews)
6-Acre Luxurious Country Home with Goddess Point Lookout
Woodbury, CT
8% off
Price is NZ$9,848
NZ$9,848
NZ$1,407 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$5,365
NZ$5,365
NZ$766 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$8,956
NZ$8,956
NZ$1,279 per night
includes taxes & fees
Image gallery for My favorite place!
9.49.4 out of 10 rating
Exceptional
(6 reviews)
My favorite place!
Danbury, CT
8% off
Price is NZ$12,234
NZ$12,234
NZ$1,748 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 NZ$9,103
NZ$9,103
NZ$1,300 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(32 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is NZ$6,810
NZ$6,810
NZ$973 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 NZ$3,484
NZ$3,484
NZ$498 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$9,268
NZ$9,268
NZ$1,324 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
(22 reviews)
Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!
Roxbury, CT
12% off
Price is NZ$2,571
NZ$2,571
NZ$367 per night
includes taxes & fees
Image gallery for Charming Cottage in Washington Depot
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Charming Cottage in Washington Depot
Washington Depot, CT
8% off
Price is NZ$4,798
NZ$4,798
NZ$685 per night
includes taxes & fees
Image gallery for Private Kent Getaway With Views, Pond & Pool
1010 out of 10 rating
Exceptional
(15 reviews)
Private Kent Getaway With Views, Pond & Pool
Kent, CT
8% off
Price is NZ$4,160
NZ$4,160
NZ$594 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
(17 reviews)
Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
Harwinton, CT
7% off
Price is NZ$3,253
NZ$3,253
NZ$465 per night
includes taxes & fees
Image gallery for Romantic Botanical Glamping with pool, gardens & smoked dinner for 2 available.
1010 out of 10 rating
Exceptional
(16 reviews)
Romantic Botanical Glamping with pool, gardens & smoked dinner for 2 available.
Southbury, CT
8% off
Price is NZ$2,892
NZ$2,892
NZ$413 per night
includes taxes & fees
Image gallery for Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
1010 out of 10 rating
Exceptional
(8 reviews)
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
New Fairfield, CT
8% off
Price is NZ$7,905
NZ$7,905
NZ$1,129 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 NZ$2,871
NZ$2,871
NZ$410 per night
includes taxes & fees
Image gallery for Charming apartment 7 minute walk to downtown
1010 out of 10 rating
Exceptional
(11 reviews)
Charming apartment 7 minute walk to downtown
Torrington, CT
8% off
Price is NZ$2,167
NZ$2,167
NZ$310 per night
includes taxes & fees
Image gallery for The Long View of Candlewood Lake
1010 out of 10 rating
Exceptional
(21 reviews)
The Long View of Candlewood Lake
New Milford, CT
8% off
Price is NZ$7,581
NZ$7,581
NZ$1,083 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
9.89.8 out of 10
Exceptionalexceptional
Cozy Cabin @ Sticks & Stones Farm
Sleeps 4 · 2 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
5 reviews(5 reviews)
Modern cozy home, pet friendly
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
One Bedroom Apartment in Southford/Southbury, CT
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1-bedroom vacation home 22 minutes from Quinnipiac University
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
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