Best Vacation Homes in Woodbury
1380 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $239/Night
For 7 Nights US $1,672
1840.63 ft²
7 Guests
1 Bedroom
2 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $437/Night
For 7 Nights US $3,057
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,629/Night
For 7 Nights US $11,400
4 Guests
2 Bedrooms
2 Bathrooms
Couples Retreat
Cabin
- Fireplace/Heating
- Pet Friendly
- Parking
US $428/Night
For 7 Nights US $2,999
1496.18 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Spa
- Fireplace/Heating
- Pet Friendly
US $328/Night
For 7 Nights US $2,298
600 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $184/Night
For 7 Nights US $1,290
889 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $258/Night
For 7 Nights US $1,807
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $204/Night
For 7 Nights US $1,425
Woodbury Luxury Rentals
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,723/Night
For 7 Nights US $12,062
69965 ft²
20 Guests
7 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
US $1,589/Night
For 7 Nights US $11,121
2400 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,533/Night
For 7 Nights US $10,730
3800 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
US $1,311/Night
For 7 Nights US $9,177
4298 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,122/Night
For 7 Nights US $7,857
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,101/Night
For 7 Nights US $7,704
2050 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,030/Night
For 7 Nights US $7,212
3100 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,027/Night
For 7 Nights US $7,189
Woodbury Pet Friendly Vacation Rentals
6 Guests
4 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $244/Night
For 7 Nights US $1,711
1377.78 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $243/Night
For 7 Nights US $1,703
2800 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $374/Night
For 7 Nights US $2,616
8 Guests
3 Bedrooms
1 Bathroom
Apartment
- Pet Friendly
- Parking
- Air Conditioner
US $158/Night
For 7 Nights US $1,106
1850 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $387/Night
For 7 Nights US $2,707
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $702/Night
For 7 Nights US $4,911
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,022/Night
For 7 Nights US $7,157
2400 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,002/Night
For 7 Nights US $7,012
Woodbury Large Vacation Homes
3800 ft²
12 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,023/Night
For 7 Nights US $7,164
3326.05 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $804/Night
For 7 Nights US $5,626
3321 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $797/Night
For 7 Nights US $5,577
2200 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $632/Night
For 7 Nights US $4,423
14 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,395/Night
For 7 Nights US $9,765
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $847/Night
For 7 Nights US $5,930
3000 ft²
6 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $588/Night
For 7 Nights US $4,115
5800 ft²
19 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Air Conditioner
US $1,336/Night
For 7 Nights US $9,351
Why Choose Rent By Owner for your Woodbury Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Woodbury
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this charming destination can enhance your experience, allowing you to enjoy its natural beauty and local ambiance at its best.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the area experiences pleasant weather perfect for outdoor activities and exploring local scenery, making it an ideal period to enjoy your vacation rental.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Early Fall (September to October)
This season offers mild temperatures and beautiful autumn foliage, providing a cozy and scenic atmosphere for your stay in the region.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Mid Winter (January to February)
The cold winter months bring lower occupancy rates, offering a more peaceful experience when booking your vacation rentals here.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Late Fall (November to December)
As the region transitions into winter, fewer visitors are around, allowing you to enjoy a tranquil retreat in your preferred accommodation.
Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F
Weekly Weather Forecast for Woodbury
How to Book Your Woodbury Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Woodbury
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a spacious backyard for relaxing or entertaining outdoors.
- Take advantage of a swimming pool, perfect for cooling off during warm summer days in the area.
- Make use of a well-maintained patio area ideal for al fresco dining and gatherings.
- Explore nearby walking trails or scenic paths that are conveniently accessible from your rental.
- Benefit from a fire pit or outdoor fireplace for cozy evenings under the stars.
- Access to outdoor sports amenities such as tennis courts or golf courses within driving distance.
- Appreciate beautifully landscaped gardens or flower beds that enhance your outdoor experience here.
Top Attractions Around Woodbury
What attractions are nearby?
Within this charming area, you can enjoy a variety of outdoor activities and cultural experiences that highlight the natural beauty and rich history nearby your vacation rental in Woodbury, Connecticut.
Family Activities
- Woodbury Town Park: Enjoy a family picnic and outdoor games in this scenic park, perfect for relaxing days with children.
- The Woodbury Ski Area: Experience winter fun through skiing or snowboarding, making it an ideal activity for active families during the colder months.
- Fairview Tree Farm & Market: Explore a charming farm environment where you can pick seasonal fruits and learn about local agriculture together.
- Lake Quassapaug: Spend a day by the lake swimming, paddle boating, or simply unwinding in the tranquil surroundings of this natural retreat.
Adult Activities
- Visit the Woodbury Historic District: Explore this charming area to appreciate well-preserved architecture and learn about the region's rich history.
- Enjoy outdoor activities at I-84 Riverside Park: Engage in leisurely picnics, nature walks, or simply relax by the scenic river setting that offers a peaceful escape nearby.
- Discover local art and craftsmanship: Browse unique galleries and artisan shops showcasing the region’s creative talents, perfect for a cultural afternoon.
- Tour the nearby Silver Sands State Park: Take advantage of this beautiful coastal park for walking, birdwatching, or unwinding on sandy beaches just a short drive from here.
Other Places to Stay in Woodbury, CT
Woodbury Ski Area
Flanders Nature Center
Bariatric Summit
Glebe House Museum and The Gertrude Jekyll Garden
Hollow Park
Pilgrim Mall Shopping Center
Woodbury Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining and shopping options: Take advantage of the area’s unique shops and eateries to experience authentic regional flavors and craftsmanship during your stay.
- Plan outdoor activities: Make the most of the scenic surroundings by enjoying activities like hiking or nature walks that showcase the natural beauty here.
- Visit nearby cultural sites: Discover the region’s history and arts through local landmarks and cultural attractions, enriching your travel experience.
- Book well in advance: Secure your preferred vacation rentals early to ensure a comfortable and stress-free visit to this popular destination.
Transportation Options
- Woodbury Bus Service: This local bus service offers convenient transportation options throughout the area for easy access to key destinations.
- Connecticut Amtrak Station: Located within a reasonable drive, Amtrak provides reliable rail travel connecting you to major cities across the region.
- Car Rentals at Regional Airports: Several rental agencies operate nearby airports, giving you flexible transportation options during your stay here.
- Taxi and Rideshare Services: Accessible through popular apps, these services provide quick and dependable transportation around this destination’s vicinity.
Local Customs Options
- Local Farmer's Markets: Visiting these markets is a great way to experience the region’s farm-to-table traditions and support local artisans while staying in your chosen vacation rental.
- Historic Preservation Practices: Respect for the area's historic sites and architecture reflects the community’s appreciation of its heritage, often observed during neighborhood events and tours.
- Community Festivals and Fairs: Participating in seasonal festivals offers insight into the area’s cultural identity and provides an authentic local experience close to your vacation rental.
- Traditional Craftsmanship: The region’s emphasis on handmade goods and craftsmanship can be seen through local shops and artisan studios, enriching your understanding of local customs here.
Woodbury Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Woodbury?
There are a lot of options in Woodbury. If you plan on staying in the Woodbury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Woodbury:
- Charming 1760 Cape Nestled in the Foothills of Litchfield County
- Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
- Cozy One Bedroom Apartment Centrally Located in Southbury
- Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
- 1.5HrsNYC, Best Skiing, Shopping, Dining PoshPadsCT "MOOSEHORN"
- 6-Acre Luxurious Country Home with Goddess Point Lookout
- Nature & Luxury @Lavender Lake Est (Kosher optional)
- Cozy family and pet friendly 3BR Home
- Walk to Memorial Park: Pet-Friendly Bethlehem Home
- STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit
2. How many vacation rentals have private pools in Woodbury?
There are 5 vacation rentals with private pools near Woodbury. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Woodbury are best for families?
If you are looking for a family-friendly vacation home in Woodbury, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Woodbury:
4. How many Rentbyowner vacation rentals are available in Woodbury?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 86 in the Woodbury area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Woodbury.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the property owner. It's important to read the specific listing details or contact the host directly to understand the terms and any potential fees associated with cancellations.
6. Are there minimum stay requirements for booking in this destination?
Minimum stay requirements can differ between properties. Be sure to check each listing's details or reach out to the owner to confirm any minimum night stays before booking your trip.
7. How do I find out about the amenities included with my vacation rental in the region?
Amenities are listed in each property’s description, but for any questions or special requests, contacting the host directly will provide the most accurate information to ensure the rental meets your needs.
8. What steps should I take to ensure a smooth check-in process at my chosen property?
Check the property listing for specific check-in instructions, and communicate with the host beforehand if needed. Many hosts offer flexible check-in options to accommodate your travel schedule.
9. Is there any support available if I encounter issues during my stay?
Support details are typically provided by the property owner or local management. Contact information is usually available in your booking confirmation, allowing you to resolve any concerns promptly.
Woodbury Top Rated Vacation Rentals
279.86 ft²
5 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Hot Tub
US $230/Night
For 7 Nights US $1,607
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $158/Night
For 7 Nights US $1,103
US $107/Night
For 7 Nights US $746
99.57 ft²
12 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $151/Night
For 7 Nights US $1,055
8 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Kitchen
US $1,167/Night
For 7 Nights US $8,168
3500 ft²
12 Guests
6 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,057/Night
For 7 Nights US $7,398
14 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $851/Night
For 7 Nights US $5,954
18 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $1,718/Night
For 7 Nights US $12,026
