Vacation rentals in Woodbury

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Top-rated vacation rentals in Woodbury

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Top guest favorite

A charming house with a mix of stone and siding is presented, surrounded by lush greenery and trees. The two-story structure features a prominent stone chimney. A pathway leads from the front yard, creating a welcoming entrance to this serene setting.

Home in Brookfield

4.98 out of 5 average rating, 148 reviews

Stay at Old Dorset Farm & create lifelong memories

This 1905 Historic Old Bakery is the perfect location to create lifelong memories while exploring quaint New England. Set on 4 acres, with a lake, trails and golden rolling hills just minutes away, you’ll enjoy all of New England's beauty. Hiking, kayaking, antiques shopping or gallery visiting... it can all be done right here. But you don't have to go anywhere. The two fireplaces invite you to just stay, relax and enjoy the complimentary bottle of Prosecco. Follow us on Insta: @Old_Dorset_Farm

Top guest favorite

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

Guesthouse in Southbury

4.93 out of 5 average rating, 320 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).

Top guest favorite

An outdoor porch area features a white Adirondack chair positioned on light gray decking. Sunlight creates shadows across the floor, with green foliage visible in the background, providing a serene setting for relaxation.

Apartment in Southbury

5 out of 5 average rating, 20 reviews

New Apartment Centrally Located in Southbury

Keep it simple at this peaceful and centrally-located apartment. Recently renovated with all the essential amenities to make your stay just like home. Wi-Fi, washer, dryer, cooktop, fridge, oven, microwave, toaster, smart TV and Keurig are ready to make your stay pleasant. An outdoor porch is available for dining in warmer months. It includes one new queen bed plus sofa bed for one adult or two kids. Located just minutes from shopping and dining in downtown Southbury with easy access to 84

Top guest favorite

A spacious kitchen drawer is filled with various labeled spice jars, organized neatly in rows. The collection includes herbs and spices such as basil, cumin, and chili powder, offering convenience for cooking. A few larger jars are also present among the smaller containers.

Home in Woodbury

4.99 out of 5 average rating, 129 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this sanitized, rambling, relaxing, light-filled 2 story 4 bedroom 2.5 bath on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from 5 popular, fabulous restaurants. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."

Guest favorite

The bathroom features warm orange walls and a tiled floor. A white toilet is positioned against one wall, with a mounted toilet paper holder nearby. Two dark wooden shelves are installed above a sleek countertop, providing space for toiletries or storage.

Guest suite in Watertown

4.91 out of 5 average rating, 194 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

A cozy living space features a patterned sofa adorned with various throw pillows. Nearby, a light-colored stool complements a wooden coffee table, while a textured area rug adds warmth to the room. Decorative woven baskets are displayed on the wall above the sofa.

Guest suite in Bethlehem

4.99 out of 5 average rating, 296 reviews

Breezy Crest cozy, private retreat 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!

Guest favorite

An open-concept living area features wooden ceilings and a bamboo floor. A sectional sofa and coffee table are positioned beside a dining table for four. Sliding glass doors provide access to an outdoor space, while large windows allow natural light to fill the cozy atmosphere.

Cottage in Bethlehem

4.98 out of 5 average rating, 103 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

A kitchen countertop displays coffee-making appliances, including a standard coffee maker and a Keurig machine. Various coffee supplies are arranged nearby, including coffee pods, creamer, and a canister of ground coffee. The backdrop features vibrant blue walls.

Apartment in Waterbury

4.99 out of 5 average rating, 102 reviews

Everything you need! Apartment!

Awesome bright 2nd floor apartment, has everything you need for your stay. Full Kitchen, Laundry and is in an very convenient and safe area. Walking distance to several restaurants and bars. Easy access to highway. Garage may be available. Ask for details. Plenty of on-street parking. Quiet area, On cul-de-sac. Wi-Fi, Netflix, Prime, Direct TV (Note: I do use the garage below the unit for a card game every 2 weeks from approximately 7 PM to 11:30 PM) Does not affect your stay.

Guest favorite

A rustic game room features wooden walls with a rich texture, complemented by a pool table at the center. A long table lined with benches offers seating, while various artworks are displayed on the walls. Soft lighting adds to the inviting ambiance.

Apartment in Brookfield

4.92 out of 5 average rating, 279 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Top guest favorite

A compact bathroom features a white pedestal sink against a backdrop of textured brown wooden panels. A mirror framed in distressed wood hangs above the sink, while a framed art piece is displayed on the wall. A silver towel rack and toiletries are neatly arranged.

Home in Bethlehem

4.97 out of 5 average rating, 296 reviews

Litchfield County Farmhouse with a Modern Twist

Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Top guest favorite

A small outdoor patio area features a round glass table surrounded by two black wicker chairs. The space overlooks a grassy area with lush trees in the background, creating a serene environment for outdoor relaxation.

Home in Southbury

4.99 out of 5 average rating, 120 reviews

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working (in progress) farm bordered by 155 acres of protected land trust with marked hiking trails. Southford Falls and Kettletown State Park are within minutes for fishing, picnicking, and hiking. 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.

Top guest favorite

A well-equipped kitchenette is featured, highlighted by warm wooden cabinetry and black countertop. Small appliances include a microwave and coffee maker, with a compact dining table positioned near a window adorned with layered curtains. Natural light illuminates the space, enhancing its inviting ambiance.

Apartment in Bethlehem

4.94 out of 5 average rating, 250 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.

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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

Superhost

A welcoming entryway features a light grey wall with a decorative mirror above a small, dark wooden table. A patterned area rug is situated on the floor, and natural light enters through the adjacent doorway, enhancing the open feel of the space.

Apartment in Watertown

4.9 out of 5 average rating, 31 reviews

Steele Brook Manor

ColetteRating, 5 stars1 week ago

Very quaint typical New England home. We absolutely loved it and will be returning on a regular basis next year as it’s very convenient for us with our daughter at the local boarding school. Clean, tidy, free of clutter and very comfy. Good delivery service available from local restaurants if you don’t feel like going out. We were exhausted after packing up our daughters dorm room and just wanted to stay in. It felt like a home away from home .

A serene outdoor scene depicts two horses grazing in a lush, green pasture surrounded by trees. Fencing outlines the area, and a dusty patch indicates a space for activity. The sky shows soft clouds, contributing to the peaceful environment of the farm.

Cottage in Woodbury

4.75 out of 5 average rating, 4 reviews

The serenity farm cottage

KellyRating, 5 stars8 months ago

I was in a pinch to find a place quickly and stumbled upon Marie’s cottage. I’ve been a rider for nearly 20 years…so a horse rescue was ideal for me. The cottage is a lovely space with many horse decor accents. Marie was delightful and shared her rescue story with me at my request. The cottage is well stocked with all the basics you need. The bed was very comfortable—loved the cotton sheets and comforter. It was an incredibly peaceful location. In the morning, I opened the curtains and watched the horses as I drank my coffee. I really enjoyed my stay and will definitely return.

Guest favorite

A spacious dining area features a wooden table surrounded by beige chairs. Large glass doors provide access to the deck, allowing natural light to fill the room. The kitchen is equipped with modern appliances, including a stainless steel refrigerator and stove, set against light wood cabinetry.

Home in Woodbury

4.9 out of 5 average rating, 60 reviews

Family-Friendly Woodbury Home with Yard + Deck!

ForrestRating, 5 stars1 month ago

Lovely quiet home

Guest favorite

An outdoor porch features a round table surrounded by two white wicker chairs with navy cushions. A red umbrella provides shade. Lush greenery is visible in the background, and sunlight filters through the leaves, creating a serene atmosphere.

Guest suite in Woodbury

4.96 out of 5 average rating, 27 reviews

NewEngland Apart/Woodbury Bike trail&Peaceful!

AdamRating, 5 stars3 weeks ago

Would highly recommend! Space was private and well thought out. Furnishings and included extras were just the right touch. On top of that, Alan is a fantastic host. Would stay here again in a heartbeat!

Superhost

A private wooden deck is framed by greenery, featuring two metal chairs and a small table with potted flowers and a pumpkin. The entrance to the studio is visible, characterized by a wooden door set against a rustic, sloped roof.

Guesthouse in Southbury

4.93 out of 5 average rating, 69 reviews

The Nest. Large studio in the Woods.

DougRating, 5 stars2 weeks ago

Unique stay in a equally unique natural setting. Marianne was supportive, generous, and gracious.

Top guest favorite

A bright and airy living area features a comfortable seating arrangement with a grey sofa, accented by decorative cushions. Natural light enters through multiple large windows, highlighting the rich wooden floor. A desk and ergonomic chair are positioned alongside a window, creating a functional workspace.

Home in Roxbury

5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars3 months ago

My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.

Top guest favorite

A small bedroom features a black metal bed frame with a striped bedspread and decorative pillows. Two bedside tables with lamps provide illumination. Natural light enters through a window, while map prints are displayed on the wall. Soft seating is offered by two poufs.

Home in Bridgewater

5 out of 5 average rating, 17 reviews

Mid-Mod 2BR Cottage in CT Woods

CarlaRating, 5 stars5 months ago

We enjoyed our stay very much. The area is very cute and not far to go into New Milford or New Preston to explore. The home is lovely and very clean. The mattress provided us with the best sleep ever. The kitchen was a focal point and it was great for cooking. Our host was very nice and available for questions. We found it be a little gem and would highly recommend staying there.

Guest favorite

Home in Bethlehem

5 out of 5 average rating, 9 reviews

Woodland Retreat w/Fireplace - Quiet & Cozy

Mary EllenRating, 5 stars3 months ago

The house was very clean, open plan layout, and comfortable for family gatherings. Beautiful setting surrounded by nature. Well stocked with every convenience one could think of. Highly recommend

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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

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