What are the most popular amenities for House Rentals in Woodbury?

Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with air conditioning, over 10 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Are there family-friendly vacation rentals in Woodbury?

Woodbury has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Are there vacation rentals with a dedicated workspace in Woodbury?

Yes! Work meets play with ease at over 20 vacation rentals in Woodbury featuring dedicated workspaces. Stay connected and productive in your home away from home.

Do house rentals in Woodbury have a kitchen?

Absolutely! We offer over 10 house rentals with a kitchen in Woodbury. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Woodbury have air conditioning?

Absolutely! We offer over 20 house rentals with air conditioning in Woodbury. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Woodbury have wifi?

Absolutely! We offer over 20 house rentals with wifi in Woodbury. Enjoy a tailored experience with all the comforts you desire.

Are there pet-friendly vacation rentals in Woodbury?

Four-legged friends are welcome in Woodbury. Choose from more than 10 vacation rentals for guests traveling with pets.

Do house rentals in Woodbury have free parking?

Absolutely! We offer over 20 house rentals with free parking in Woodbury. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Woodbury

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Woodbury

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.

Guesthouse in Southbury

4.93 out of 5 average rating, 344 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favorite

A brick fireplace is centered against a light green wall, featuring a clock above it. A patterned chair is positioned nearby, alongside a small television stand. A woven rug covers the floor, enhancing the cozy atmosphere of the space.

Guest suite in Watertown

4.91 out of 5 average rating, 203 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Top guest favorite

The exterior of the rental space features light-colored siding with a welcoming black door. A small outdoor dining area is provided with a round table and chairs, nestled beside a well-maintained garden area with greenery and stone accents.

Guest suite in Bethlehem

4.99 out of 5 average rating, 321 reviews

Quiet cottage w/chickens, gardens near Litchfield

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and summer fun!

Top guest favorite

An aerial view captures a sprawling farm landscape at sunset, with the sun dipping behind rolling hills. The guest house, white with a gray roof, is surrounded by green fields and lush vegetation, creating a serene atmosphere.

Farm stay in New Milford

5 out of 5 average rating, 124 reviews

Farm House

A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers we sell at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, chickens, barn cats and a resident farm dog, Finula. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

Guest favorite

An outdoor fire pit is surrounded by several adirondack chairs on a grassy area. A stone wall frames the fire pit, with trees and a glimpse of a secondary building in the background. The scene reflects a serene natural setting.

Cottage in Bethlehem

4.98 out of 5 average rating, 118 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Top guest favorite

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

4.99 out of 5 average rating, 124 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Top guest favorite

A spacious room features a comfortable bed with a light blue quilt, complemented by decorative pillows. A desk and chair are positioned by a window, with bookshelves in the background. Natural light filters through the windows, creating a welcoming atmosphere.

Guest suite in Morris

4.99 out of 5 average rating, 414 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own lounging/dining area. Guests have their own separate entrance & parking space(s). Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing & just 10 minutes to Washington Depot. We've recently made some updates in response to guests' feedback!

Top guest favorite

A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.

Home in Southbury

4.98 out of 5 average rating, 131 reviews

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. The holidays are right around the corner. Holiday reservations have date restrictions. Please inquire about availability. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two.

Guest favorite

A bright bedroom features a four-poster bed adorned with a floral comforter and decorative pillows. Natural light fills the room through multiple windows, which are dressed with patterned curtains. A bedside lamp and a small nightstand are positioned beside the bed.

Home in Woodbury

4.94 out of 5 average rating, 100 reviews

Ferris House: Private 19th Century Home

Private 19th century home situated in a beautiful garden setting. Gourmet kitchen. Well appointed rooms. New England charm at its best. Enjoy nearby top restaurants and antique shops. We are also very close to private schools in the area such as Taft and Westover, which makes this an excellent location for visiting family and friends. We welcome couples, solo adventurers, business travelers and families (with kids).

Top guest favorite

A spacious living room is characterized by a comfortable sofa adorned with decorative pillows. Two lamps provide soft lighting, while a coffee table displays decorative items. A wall-mounted clock and artwork complement the vaulted ceiling, creating a cozy ambiance in the inviting space.

Apartment in Bethlehem

4.94 out of 5 average rating, 252 reviews

Cozy 2nd Floor Suite In Bethlehem CT

Our private 2nd floor suite is fully equipped and easy on the budget. Sleeps a single or couple in comfort in queen bedroom. PLEASE NOTE- There is only one bed. This property is not suitable for friends traveling together unless they are willing to share the queen bed. Spacious living room and well-equipped kitchenette. Dedicated workspace. Relax with Wi-Fi, streaming channels. Free calls anywhere in the US.

Guest favorite

A studio space is highlighted by a colorful patterned bedspread covering a spacious bed. A comfortable gray sectional sofa offers seating, and a coffee table sits in front. A kitchen area with modern appliances is visible in the background, enhancing the functionality of the space.

Apartment in Southbury

4.86 out of 5 average rating, 111 reviews

Suite Hill Studio

A private entrance to your studio located at the top of a hill. Surrounded by trees. Tranquility can be found. We are located near the Antique trail of Southbury. Its a 25 min ride to Danbury or 20 min ride to Waterbury. Just under 2 hours to NYC. And a little over 2 hours to Boston. We can provide a daily clean at an additional cost. They are grocery stores, TJ. Maxx and Starbucks within minutes.

Superhost

The spacious living area features a large gray sectional sofa and a flat-screen television. An expansive window offers a view of greenery outside, while natural light brightens the room. A wooden dining table is positioned nearby, enhancing the room's functionality.

Vacation home in Woodbury

4.86 out of 5 average rating, 29 reviews

UNIQUE and GORGEOUS historic loft style rental

Beautifully bright third floor loft style space with private entry available for your enjoyment. Basic kitchen, laundry, and bath are located on the second floor. Due to the stairs in this unique space, it would be ideal for a single traveler or couple looking for a getaway. Walkable to historic Woodbury, minutes to amazing land trust hiking trails in Roxbury, and only 1.5 hours from NY City.

Vacation rentals for every style

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Popular amenities for Woodbury vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Woodbury

Home in Watertown

5 out of 5 average rating, 4 reviews

Modern Ranch style apartment.

The exterior of the cottage is depicted, showing a single-story structure with a sloped roof. A small porch with seating is visible, surrounded by lush greenery. A gravel path leads to the entrance, and a garage is seen on one side of the building.

Cottage in Woodbury

4.7 out of 5 average rating, 10 reviews

The serenity farm cottage

Superhost

The exterior of a blue house features multiple dormer windows and a red front door. A wooden deck extends along the front, with small shrubs planted on either side. The yard is grassy, surrounded by tall trees, contributing to a serene environment.

Home in Southbury

4.84 out of 5 average rating, 37 reviews

Cozy cute Relaxing home

A cozy living area features a dark leather sectional couch surrounding a glass coffee table, with a soft rug underneath. Exposed wooden beams accent the ceiling, and a fireplace is situated in a brick alcove. A television is mounted above the mantel, contributing to a relaxed atmosphere.

Home in Woodbury

4.69 out of 5 average rating, 16 reviews

Cozy Vintage Cottage

Guest favorite

The exterior of the cozy cottage is presented, showcasing a light blue facade and a welcoming front porch with multiple windows. A garden area is visible in front, featuring freshly mulched flower beds. Surrounding trees provide a natural backdrop, enhancing the peaceful setting.

Home in Bethlehem

4.83 out of 5 average rating, 6 reviews

Cozy Pet Friendly Lake Cottage!

Guest favorite

An outdoor deck is furnished with a circular table and four chairs, surrounded by a wooded landscape. The scene features bare trees with a clear sky and soft clouds, providing a serene atmosphere for relaxation or dining outside.

Home in Woodbury

4.9 out of 5 average rating, 62 reviews

Family-Friendly Woodbury Home with Yard + Deck!

Guest favorite

An aerial view showcases the expansive stone-paved backyard, featuring a large swimming pool surrounded by lounge chairs. Lush greenery borders the area, contributing to a serene outdoor atmosphere. The image captures the inviting space, perfect for relaxation and leisure.

Guest suite in Watertown

4.96 out of 5 average rating, 46 reviews

Hidden Serenity at TuKasa - Pool & Billiards

Top guest favorite

The outdoor area features the vintage Airstream surrounded by a gravel patio with seating, a fire pit, and stacked firewood. An umbrella provides shade over a dining table, while string lights add warmth to the inviting forest setting.

Camper/RV in Wassaic

5 out of 5 average rating, 38 reviews

Airstream Forest Glamping near Metro North Train

Show all

Quick stats about vacation rentals in Woodbury

Total rentals
30 properties
Total number of reviews
640 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

What are the most popular amenities for House Rentals in Woodbury?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with air conditioning, over 10 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Woodbury?
Woodbury has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Woodbury?
Yes! Work meets play with ease at over 20 vacation rentals in Woodbury featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Woodbury have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Woodbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodbury have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Woodbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodbury have wifi?
Absolutely! We offer over 20 house rentals with wifi in Woodbury. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Woodbury?
Four-legged friends are welcome in Woodbury. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Woodbury have free parking?
Absolutely! We offer over 20 house rentals with free parking in Woodbury. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Woodbury

Top-rated vacation rentals in Woodbury

Vacation rentals for every style

Popular amenities for Woodbury vacation rentals

Other great vacation rentals in Woodbury

Quick stats about vacation rentals in Woodbury

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Wifi availability

Frequently Asked Questions

Destinations to explore