Top Winter Vacations - Vacation Rentals in Woodbury

Walk to Memorial Park: Pet-Friendly Bethlehem Home From US $232
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
New One Bedroom Apartment Centrally Located in Southbury From US $129
         

Luxury Places to Stay in Woodbury

Over 65+ Luxury Places to Stay in or Near Woodbury
6-Acre Luxurious Country Home with Goddess Point Lookout From US $1,723
         

10.0 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Nature & Luxury @Lavender Lake Est (Kosher optional) From US $1,220
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Woodbury

Over 20+ Top-Rated Vacation Rentals with a Pool in or Near Woodbury
Heritage Hotel, Golf, Spa & Conference Center From US $235
         

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8.4 (425 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Wyndham Southbury From US $133
         

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8.2 (1051 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Wyndham Southbury From US $113
         

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7.6 (794 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious Woodbury Home w/Pool + Hot Tub! From US $773
         

7.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Welcome to Hidden Haven, a simply serene getaway From US $1,167
         

Pet-Friendly Vacation Rentals in Woodbury

Over 25+ Pet-Friendly Vacation Rentals in or Near Woodbury
Family-Friendly Woodbury Home with Yard + Deck! From US $245
         

9.6 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Family-Friendly Woodbury Home with Yard and Deck! From US $148
         

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9.8 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
Guest Cottage on Country Estate From US $214
         

9.2 (42 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Roxbury Cabin Retreat
New
From US $311
         

New
Cabin
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Cozy family and pet friendly 3BR Home From US $476
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit From US $702
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Clean & Bright 2 Bedroom Cottage shares 8 Acres From US $210
         

10.0 (5 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Woodbury on PetFriendly.io

Large Vacation Homes & Villas in Woodbury

Over 11+ Large Vacation Homes & Villas in or Near Woodbury
Classic Roxbury Home w/Picturesque Backyard! From US $588
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Gather your family at this country estate From US $347
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
NEW LISTING! BlackWoods Old Country Home by RedAwning
New
From US $1,395
         

9.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
BlackWoods Old Country Home From US $851
         

9.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Woodbury Cottage w/ Fire Pit & Pool! From US $579
         

Gather your family at this country estate From US $340
         

4.6 (27 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible

Wheelchair Accessible Vacation Homes in Woodbury

Over 1+ Wheelchair Accessible Vacation Homes in or Near Woodbury

Woodbury Varoom and Airbnb Places to Stay Under $200

Over 14+ Woodbury Varoom and Airbnb Places to Stay Under $200
Walk to Memorial Park Pet-Friendly Bethlehem Home From US $138
         

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9.5 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Accessibility
The Milestone Inn From US $119
         

8.8 (190 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Tranquil setting in the hills of Litchfield County From US $158
         

4.8 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Loft Studio on Organic Farm From US $134
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Charming Converted Barn From US $90
         

New
House
  • Air Conditioner
  • Pet Friendly
  • TV

Instantly Bookable Vacation Homes in Woodbury

Over 4+ Instantly Bookable Vacation Homes in or Near Woodbury
Spacious Watertown Apt ~ 4 Mi to State Park From US $249
         

8.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Woodbury Vacation Rentals

With more than 74 Woodbury vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Topwintervacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Woodbury.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Topwintervacations Woodbury, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Woodbury. Places to stay near Woodbury are 2128.73 ft² on average, with prices averaging $552 a night.

Topwintervacations makes it easy and safe to find and compare vacation rentals in Woodbury with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Woodbury

Type Count
Vacation Homes 46
Holiday Apartments 15
Hotels with Suites 5
Cottages 4
Cabin Rentals 2
B&B 1

Use these Quick Filters to Find a Vacation Rental in Woodbury

Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations 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.

Weather in Woodbury

View the weather forecast for Woodbury before booking your Woodbury 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