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Vacation rentals in Woodbury

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Top-rated vacation rentals in Woodbury

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Home in Brookfield

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

Guesthouse in Southbury

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 suite in Watertown

Private King suite w/ separate entry-Walk to Taft!

Enjoy Litchfield County, CT! This renovated 1-bedroom guest suite in an 1859 historic home has a private entrance off a dedicated covered porch. Enter through the private stairway into the bedroom with a King size bed and comfortable foam mattress. French doors open into a living room with a pullout full size sofa bed and a Nespresso coffee maker. The renovated bath has marble floors and a glass door shower. Free parking for up to two cars in the drive and directly across the street from Taft.

Guest suite in Watertown

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!

Home in Woodbury

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 suite in Bethlehem

Breezy Crest private & restful w/antique charm

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 ski slopes.

Cottage in Southbury

Sun Filled Cottage

Sweet little front porch overlooks rolling farm land to the West. Light, bright sun filled cottage features great room, Vermont Cast wood stove (fireplace) 70" SMART TV, full size washer/dry, glass doors to back deck for private lounging. kitchen w/ dishwasher, stove/oven & new fridge. 2 bedroom guest cottage on 8 AC estate w/ room to walk & explore! 5 min to groceries, dining & Woodbury Antique district. 7 minutes to Exit 15 on I-84. River front dog-park nearby. WIFI ,Air-conditioning

Farm stay in Bethlehem

The Loft @ Sun One Organic Farm

Designed by a Yale educated Architect, The Loft @ Sun One Organic Farm is ready for occupancy. Completed in 2023, The Loft features white oak floors, a chandelier and fantastic views of our farm. Located at the end of our barn yard, the loft sits on our 65 acres farm that await you to explore. Below the loft is your own private bathroom. The loft has a desk and great WIFI service. Next to the loft is our another Airbnb, Our Silo, which is available for rent.

Rental unit in Brookfield

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.

Guesthouse in Southbury

The Nest. Large studio in the Woods.

New large studio on secluded property at the end of the country road. Surrounded by trees and across the river from the National Audubon, bird sanctuary. 5 minutes from I-84. 4 minutes from town and 1 hour from Manhattan. Private, peaceful and restful. If you want to retreat to nature and rejuvenate your spirit this is the place for you. We look forward to hosting you in this lovely setting and sharing our favorite list of walking trails.

Guest suite in Morris

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 private lounging/dining area. Separate entrance and parking space. 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 and just 10 minutes to Washington Depot.

Home in Southbury

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

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Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Woodbury vacation rentals

Free parking on premises

Air conditioning

Stay near Woodbury's top sights

Quassy Amusement Park & Waterpark38 locals recommend

Nonnewaug Falls6 locals recommend

Hollow Park4 locals recommend

Other great vacation rentals in Woodbury

Guest suite in Washington

Custom industrial farmhouse Apt in Washington Dpt

Loft in Woodbury

Country Loft

Rental unit in Litchfield

Artist's Garden Apartment

Cottage in Bethlehem

Hot Tub | Kayaks | Lake Access | Pet Friendly

Home in Woodbury

The Chic Antique Retreat House

Guesthouse in Sharon

Cottage with a Waterfall View

Rental unit in Waterbury

Funky downtown art studio apartment.

Home in Watertown

Getaway near winery, distillery and state forest

Quick stats about vacation rentals in Woodbury

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

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 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, 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 10 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 10 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 10 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 10 house rentals with free parking in Woodbury. Enjoy a tailored experience with all the comforts you desire.

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