Choose from 15 vacation rentals located in Woodbury, Connecticut. Top filters in Woodbury include Internet / Wifi, Kitchen / Kitchenette, and TV. Prices range from $71 to $850 per night. Our most popular vacation rental types near Woodbury are Condo and Hotel.

Top vacation rentals in Woodbury

Climbing roses and wisteria frame the covered porch.
5.0
Outstanding(29 Reviews)
House
 in Woodbury
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
8 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

This House in Woodbury, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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4.8
Outstanding(2 Reviews)
House
 in Woodbury
Family-Friendly Woodbury Home with Yard and Deck!
Pets allowed · Kitchen / Kitchenette · Air conditioner

This inviting House in Woodbury can fit your needs for many types of vacations, at $96 per night.

$$$$
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Woodbury Vacation Rental | 3BR | 1.5BA | 1,500 Sq Ft | Stairs Required
4.8
Outstanding(10 Reviews)
House
 in Woodbury
Family-Friendly Woodbury Home with Yard + Deck!
6 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Experience vacation in Woodbury with our House, Family-Friendly Woodbury Home with Yard + Deck!. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Room
4.3
Excellent(186 Reviews)
Hotel
 in Woodbury
2star
The Milestone Inn
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking to create some memories in Woodbury? Look no further than our Hotel, The Milestone Inn. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.

$$$$
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Vacation rentals with internet & wifi in Woodbury

Property view
5.0
Outstanding(2 Reviews)
House
 in Woodbury
Updated 200-Yr-Old Home w/ Silo Living Space!
8 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Woodbury, at $455 per night for your next great vacation.

$$$$
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4.0
Good(3 Reviews)
Cottage
 in Woodbury
Pet-Friendly Woodbury Cottage w/ Fire Pit & Pool!
11 guests · 5 bedrooms · 3 baths
Pool · Pets allowed · Kitchen / Kitchenette

Are you ready to indulge in a relaxing getaway? Our Cottage in Woodbury has everything you need for a rejuvenating stay. Treat yourself to Pet-Friendly Woodbury Cottage w/ Fire Pit & Pool!'s exceptional amenities, such as Fireplace, Internet / Wifi and Pets allowed.

$$$$
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House
 in Woodbury
The Chic Antique Retreat House
12 guests · 6 bedrooms · 5 baths
Garden · Pool · Kitchen / Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Woodbury, at $850 per night for your next great vacation.

$$$$
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House
 in Woodbury
BlackWoods Old Country Home
14 guests · 5 bedrooms · 3 baths
Pool · Pets allowed · Kitchen / Kitchenette

Discover the beauty of Woodbury with a stay at BlackWoods Old Country Home, a top rated House with amenities such as Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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Woodbury

Woodbury travel guide

Let us help you plan your perfect Woodbury vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Woodbury, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Woodbury?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • TV

What are the must-visit tourist attractions in Woodbury, CT?

Woodbury, CT is a charming New England town with plenty of tourist attractions to explore. Here are some of the must-visit attractions for anyone looking for a fun day trip:

  • The Flanders Nature Center & Land Trust
  • The Woodbury Ski Area
  • The Nonnewaug Falls
  • The Woodbury Historical Society
Woodbury is a great place to visit for a day or weekend, with plenty of activities and attractions to keep you busy. Whether you're looking for a nature hike, skiing, or a cultural experience, Woodbury has something for everyone.

How can I get around in Woodbury, CT?

You can get around Woodbury, CT in the following ways:

  • Car
  • Taxi
  • Bus

There are a variety of car rental companies in the area, as well as local taxi services and bus lines for public transportation.

Where can I find affordable accommodation in Woodbury, CT?

Woodbury, CT offers a wide variety of affordable accommodation options. Here are four of the best:

  • Woodbury Inn: A cozy inn located in the heart of Woodbury, offering a variety of rooms and amenities.
  • Country Inn & Suites: Located just outside of Woodbury, this inn offers a great combination of comfort and convenience.
  • Hampton Inn & Suites: A modern hotel with a variety of amenities, conveniently located near downtown Woodbury.
  • Holiday Inn Express: A great value for budget travelers, with a variety of amenities and easy access to downtown Woodbury.

What is the culture like in Woodbury, CT?

Woodbury is a small town in Connecticut with a rich history and a culture that is unique to the region. Here are 5 aspects of its culture that make it special:

  • The town is known for its strong sense of community and neighborly spirit.
  • The town is home to many local businesses and shops that reflect the town’s unique character.
  • The town is known for its vibrant arts and music scene.
  • The town is home to many historic sites and buildings with deep roots in the area.
  • The town is known for its commitment to preserving its natural environment.

Is Woodbury, CT safe to travel to?

Woodbury, CT is a safe place to travel to. Here are some of the reasons why:
  • Low crime rate
  • Strong police presence
  • Friendly residents

What are the popular shopping destinations in Woodbury, CT?

Woodbury, CT is a great destination for shopping. Here are some of the popular shopping destinations in Woodbury:

  • Woodbury Commons Premium Outlets
  • Woodbury Antiques & Design Center
  • Woodbury Pharmacy & Gift Shop
  • Woodbury Library Book Store

What are the best neighborhoods to visit in Woodbury, CT?

The best neighborhoods to visit in Woodbury, CT are:

  • Woodbury Center
  • Woodbury Heights
  • Southford

Each of these neighborhoods offer something unique to visitors, from historic sites to outdoor activities. Woodbury Center is home to the Woodbury Historical Society, while Woodbury Heights is known for its scenic views. Southford is a great spot for outdoor recreation, with plenty of hiking trails and parks to explore.

Where is Woodbury, CT?

Woodbury, CT is located in Litchfield County, in the southwestern corner of the state. It is a rural town, with a population of about 9,500 people. The town was originally home to Native American tribes, and was later settled by European colonists in the 18th century.

What are the most popular vacation rental amenities in Woodbury, CT?

The most popular vacation rental amenities in Woodbury, CT include:

  • Modern kitchen with stainless steel appliances and granite countertops
  • High-speed internet access
  • Spacious living area with cozy furniture
  • Private outdoor patio or balcony
  • Luxurious bathroom with soaking tub and separate shower

Other amenities include an on-site fitness center, game room, and business center, as well as access to a heated pool and hot tub.

What are the top things to do in Woodbury, CT?

Woodbury, CT is a beautiful town with plenty of fun activities to offer. Here are some of the top things to do in Woodbury:

  • Visit the Flanders Nature Center & Land Trust
  • Explore the Matthies Grove Preserve
  • Go for a hike along the Connecticut Blue Trail
  • Play a round of golf at the Woodbury Country Club

No matter what activity you choose, you are sure to find something enjoyable to do in Woodbury, CT!

What do I need to know before visiting Woodbury, CT?

Before visiting Woodbury, CT, you should know that it is a small village in Litchfield County, Connecticut, with a population of about 3,000 people. Here are some other things to consider:

  • The town is known for its antiques, art galleries, and specialty shops.
  • There are many outdoor activities to do, such as hiking, fishing, and golf.
  • There are a variety of restaurants and cafes to explore for a taste of local cuisine.

Woodbury is a great place to visit for anyone looking for a small-town vibe with plenty of things to do. Whether it's browsing the shops, exploring nature, or tasting the local flavors, you're sure to have a great time.

What is the price range for rentals in Woodbury?

Vacation rentals in Woodbury have a price range between $71-$850. The average price for rentals in Woodbury is $455 per night.

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