99+ Vacation Rentals Near Woodbury Ski Area |
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  4. Woodbury Ski Area

Stayifyoudare - Vacation Rentals in Woodbury Ski Area

Property Image From $366
         

10.0 (47 Reviews)
House
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $671
         

10.0 (1 Review)
House
Upmarket Country Retreat, Washington, Connecticut
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $205
         

10.0 (11 Reviews)
House
139 m² House ∙ 3 bedrooms ∙ 6 guests
  • 1496 ft² House
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,629
         

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New
House
Blackwoods Old Country Home 5 Bedroom Home by RedAwning
  • Parking
  • Pet Friendly
  • Pool

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Property Image From $255
         

10.0 (33 Reviews)
Cabin
Cozy & Chic Cabin by the Lake, with access to private Beach!
  • Air Conditioner
  • Parking
  • TV

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Property Image From $370
         

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10.0 (1 Review)
House
Nature's Nest - Woodland Retreat - Fireplace - Quiet and Cozy
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $131
         

10.0 (1 Review)
Apartment
128 m² Apartment ∙ 1 bedroom ∙ 2 guests
  • 1377 ft² Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,335
         

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9.2 (53 Reviews)
Hotel
Mayflower Inn & Spa, Auberge Collection
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $404
         

10.0 (11 Reviews)
House
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $148
         

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9.5 (2 Reviews)
House
Family-Friendly Woodbury Home with Yard and Deck!
  • Parking
  • Pet Friendly
  • Accessibility

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Property Image From $773
         

New
House
308 m² House ∙ 4 bedrooms ∙ 10 guests
  • 3315 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $119
         

8.8 (190 Reviews)
Hotel
The Milestone Inn
  • Air Conditioner
  • Parking
  • TV

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Property Image From $238
         

10.0 (7 Reviews)
Apartment
Walk to Memorial Park: Pet-Friendly Bethlehem Home
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $138
         

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9.5 (2 Reviews)
Apartment
Walk to Memorial Park Pet-Friendly Bethlehem Home
  • Parking
  • Pet Friendly
  • Accessibility

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Property Image From $393
         

10.0 (6 Reviews)
Cottage
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
  • Air Conditioner
  • Parking
  • TV

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Property Image From $661
         

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New
House
Spacious Woodbury Home with Pool and Hot Tub!
  • Parking
  • Pool
  • View

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Property Image From $1,891
         

10.0 (1 Review)
House
Upmarket Country Retreat, Washington, Connecticut
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $158
         

New
Apartment
Tranquil setting in the hills of Litchfield
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,017
         

10.0 (1 Review)
House
Secluded Architectural gem in the heart of Roxbury - Modern, Chic & Dreamy Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $139
         

New
House
Outdoor Space with Stunning Views New Milford Home!
  • Parking
  • Accessibility
  • Security/Safety

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Property Image From $316
         

10.0 (1 Review)
Cabin
Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.
  • Air Conditioner
  • Parking
  • TV

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Property Image From $1,762
         

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10.0 (7 Reviews)
Hotel
The Mayflower Inn & Spa, Auberge Collection
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,173
         

9.6 (50 Reviews)
House
Litchfield County Four Season Country Paradise
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $240
         

9.6 (20 Reviews)
House
Family-Friendly Woodbury Home with Yard + Deck!
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Woodbury Ski Area.

Weather in Woodbury Ski Area

View the weather forecast for Woodbury Ski Area before booking your Woodbury Ski Area Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Woodbury Ski Area, CT

Stayifyoudare offers a large selection of top attractions around Woodbury Ski Area. Research things to do on your vacation before you visit Woodbury Ski Area.


Palace Theatre Quassy Amusement Park Candlewood Lake Elephant's Trunk Flea Market Lake Waramaug State Park Lake Waramaug Mount Tom State Park Bantam Lake Waterbury Green Southford Falls State Park Brookfield Golf Course Institute for American Indian Studies Museum and Research Center Brass Mill Center Waterbury City Hall Flanders Nature Center Holy Land USA Union Station Clocktower Abbey of Regina Laudis Squantz Pond State Park Pilgrim Mall Shopping Center