Vacation rentals near Woodbury Ski Area
We found 466 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals within easy reach of Woodbury Ski Area that provide the perfect home base for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. You'll be able to choose a rental for everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Woodbury Ski Area
Showing deals for:Nov 14 - Nov 21
Image gallery for Fabulous year round waterfront retreat on Lake Waramaug
1010 out of 10 rating
Exceptional
(6 reviews)
Fabulous year round waterfront retreat on Lake Waramaug
New Preston, CT
10% off
Price is CA $1,238
CA $1,238
CA $11,119 total
CA $11,119 total
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
10% off
Price is CA $619
CA $619
CA $5,583 total
CA $5,583 total
includes taxes & fees
Image gallery for Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
1010 out of 10 rating
Exceptional
(20 reviews)
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Danbury, CT
10% off
Price is CA $1,053
CA $1,053
CA $9,665 total
CA $9,665 total
includes taxes & fees
Image gallery for County Seat Colonial
1010 out of 10 rating
Exceptional
(11 reviews)
County Seat Colonial
Litchfield, CT
10% off
Price is CA $442
CA $442
CA $4,187 total
CA $4,187 total
includes taxes & fees
Image gallery for Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video
1010 out of 10 rating
Exceptional
(21 reviews)
Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video
Washington, CT
10% off
Price is CA $1,557
CA $1,557
CA $14,078 total
CA $14,078 total
includes taxes & fees
Image gallery for 100% WASHINGTON! PoshPadsCT "SENFF ESTATE"8-BR, 2Hrs NYC, Heated Pool, Ski, BBQ
1010 out of 10 rating
Exceptional
(16 reviews)
100% WASHINGTON! PoshPadsCT "SENFF ESTATE"8-BR, 2Hrs NYC, Heated Pool, Ski, BBQ
Washington, CT
20% off
Price is CA $2,449
CA $2,449
CA $20,790 total
CA $20,790 total
includes taxes & fees
Image gallery for Lakefront Home, Close to Mt Southington!
1010 out of 10 rating
Exceptional
(19 reviews)
Lakefront Home, Close to Mt Southington!
Wolcott, CT
10% off
Price is CA $250
CA $250
CA $2,738 total
CA $2,738 total
includes taxes & fees
Image gallery for 100% WASHINGTON! PoshPadsCT "SHEARER"2HrsNYC, 3BR, Heated Pool, Ski, BBQ, 2FPs
9.89.8 out of 10 rating
Exceptional
(11 reviews)
100% WASHINGTON! PoshPadsCT "SHEARER"2HrsNYC, 3BR, Heated Pool, Ski, BBQ, 2FPs
Washington, CT
40% off
Price is CA $864
CA $864
CA $7,613 total
CA $7,613 total
includes taxes & fees
Image gallery for Sweetbrier Farm -- Gorgeous Views, Beautiful Home
1010 out of 10 rating
Exceptional
(29 reviews)
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield, CT
15% off
Price is CA $721
CA $721
CA $6,667 total
CA $6,667 total
includes taxes & fees
Image gallery for Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Watertown, CT
10% off
Price is CA $1,247
CA $1,247
CA $11,411 total
CA $11,411 total
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
19% off
Price is CA $400
CA $400
CA $3,788 total
CA $3,788 total
includes taxes & fees
Image gallery for 100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes
1010 out of 10 rating
Exceptional
(11 reviews)
100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes
Roxbury, CT
40% off
Price is CA $970
CA $970
CA $8,542 total
CA $8,542 total
includes taxes & fees
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
20% off
Price is CA $1,981
CA $1,981
CA $17,291 total
CA $17,291 total
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
10% off
Price is CA $310
CA $310
CA $2,732 total
CA $2,732 total
includes taxes & fees
Image gallery for 100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ
9.89.8 out of 10 rating
Exceptional
(6 reviews)
100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ
Roxbury, CT
56% off
Price is CA $695
CA $695
CA $6,130 total
CA $6,130 total
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
15% off
Price is CA $760
CA $760
CA $6,933 total
CA $6,933 total
includes taxes & fees
Image gallery for Candlewood Lake Perfection: Large and very private House, property and pool.
1010 out of 10 rating
Exceptional
(18 reviews)
Candlewood Lake Perfection: Large and very private House, property and pool.
Danbury, CT
10% off
Price is CA $2,475
CA $2,475
CA $21,528 total
CA $21,528 total
includes taxes & fees
Image gallery for Best Town WASHINGTON! PoshPadsCT"51 SENFF" 2Hrs-NYC Mint 5BR, Ski, BBQ, HotTub!
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Best Town WASHINGTON! PoshPadsCT"51 SENFF" 2Hrs-NYC Mint 5BR, Ski, BBQ, HotTub!
Washington, CT
40% off
Price is CA $970
CA $970
CA $8,542 total
CA $8,542 total
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
10% off
Price is CA $805
CA $805
CA $7,532 total
CA $7,532 total
includes taxes & fees
Image gallery for Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.88.8 out of 10 rating
Excellent
(20 reviews)
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Harwinton, CT
5% off
Price is CA $217
CA $217
CA $2,285 total
CA $2,285 total
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
(12 reviews)
Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!
Bethlehem, CT
10% off
Price is CA $303
CA $303
CA $3,065 total
CA $3,065 total
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
(71 reviews)
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
Bethlehem, CT
10% off
Price is CA $285
CA $285
CA $2,480 total
CA $2,480 total
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
10% off
Price is CA $274
CA $274
CA $2,643 total
CA $2,643 total
includes taxes & fees
Image gallery for Charming apartment 7 minute walk to downtown
1010 out of 10 rating
Exceptional
(15 reviews)
Charming apartment 7 minute walk to downtown
Torrington, CT
10% off
Price is CA $200
CA $200
CA $1,849 total
CA $1,849 total
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
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Sleeps 8 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
18 reviews(18 reviews)
Spectacular Lake front house
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Sleeps 12 · 6 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
79 reviews(79 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, yards and more
More for lessMore space, more privacy, more amenities — more value