Vacation rentals in Woodbury

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Top-rated vacation rentals in Woodbury

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Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 266 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).

Oct 3 – 10

$135 per night

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 162 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!

Sep 15 – 22

$62 per night

Guest favorite

Home in Woodbury

4.99 out of 5 average rating, 111 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."

Nov 26 – Dec 3

$279 per night

Guest favorite

Loft in Woodbury

5.0 out of 5 average rating, 31 reviews

Country Loft

Sit back and relax in this recently renovated one bedroom apartment in the heart of historical Woodbury, CT. This loft-style apartment has an open floor plan, feeling spacious while still establishing moments of privacy. It is designed down to the tiniest details to be a comfortable, inviting space, perfect for anyone wanting to explore the Litchfield County area. Conveniently located on Antiques Row, the apartment is within walking distance of various attractions and the local organic market.

Mar 25 – Apr 1

$125 per night

Guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 200 reviews

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.

Sep 6 – 13

$144 per night

Guest favorite

Apartment in Litchfield

4.98 out of 5 average rating, 118 reviews

Litchfield Hills Hideaway

Enjoy the Litchfield Hills from this newly renovated one bedroom apartment with private entrance. Amenities include full kitchen, living room, bedroom with queen bed, and full en suite bathroom. WiFi and cable TV included. All located less than 2 miles from historic Litchfield Center. Our property borders on the White Memorial Foundation nature preserve, with over 40 miles of hiking trails. Mohawk Mountain Ski area in Cornwall and Ski Sundown in New Hartford are only a short drive away.

Nov 22 – 29

$120 per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 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.

Jan 23 – 30

$104 per night

Guest favorite

Home in Bethlehem

4.97 out of 5 average rating, 260 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.

Mar 12 – 19

$232 per night

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 340 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 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.

Mar 13 – 20

$82 per night

Guest favorite

Home in Southbury

5.0 out of 5 average rating, 55 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.

Sep 3 – 10

$140 per night

Guest favorite

Apartment in Waterbury

4.98 out of 5 average rating, 66 reviews

Everything you need! Apartment!

Awesome bright apartment, has everything you need for your stay. Full Kitchen, Laundry and is in an excellent area. Walking distance to several restaurants and bars. Easy access to highway. Garage available. Ask for details. Plenty of on-street parking. Quiet area, On cul-de-sac. WiFi,Netflix,Cable

Feb 26 – Mar 5

$100 per night

Guest favorite

Dome in Bethlehem

4.88 out of 5 average rating, 314 reviews

Geodesic Dome in the Wooods

A great daylight space nested on the edge of the woods. Be close to nature but also close to our house for modern convinces in our house. Please note this space is unplugged, it has no electricity, heat or air conditioning. There is a full bathrooms for your use in our basement, 125 feet away.

Nov 28 – Dec 5

$45 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Woodbury vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Woodbury's top sights

Market Place Kitchen and Bar30 locals recommend

Max Prime Steakhouse9 locals recommend

New Morning Market29 locals recommend

Dottie's7 locals recommend

Good News Restaurant and Bar22 locals recommend

San Remo Restaurant-Pizzeria3 locals recommend

Other great vacation rentals in Woodbury

Guest favorite

Home in Woodbury

5.0 out of 5 average rating, 8 reviews

Beautiful Litchfield - 2 homes in one

Oct 13 – 20

$324 per night

Guest favorite

Cottage in Southbury

4.91 out of 5 average rating, 11 reviews

Sun Filled Cottage

Jan 7 – 14

$136 per night

Guest favorite

Cottage in Bethlehem

5.0 out of 5 average rating, 31 reviews

Cottage Getaway | Peaceful Setting | Pet Friendly

Jul 14 – 21

$227 per night

Guest favorite

Home in Woodbury

5.0 out of 5 average rating, 10 reviews

The Chic Antique Retreat House

Dec 15 – 22

$765 per night

Guest favorite

Home in Waterbury

4.91 out of 5 average rating, 32 reviews

Come and enjoy the BURY's of CT!

Sep 30 – Oct 7

$162 per night

Guest favorite

Guesthouse in Southbury

4.96 out of 5 average rating, 51 reviews

The Nest. Large studio in the Woods.

Oct 7 – 14

$136 per night

Superhost

Vacation home in Woodbury

4.81 out of 5 average rating, 16 reviews

UNIQUE and GORGEOUS historic loft style rental

Oct 7 – 14

$64 per night

Guest favorite

Apartment in Bethlehem

5.0 out of 5 average rating, 77 reviews

C&C Rush Haven Farm, A Sanctuary for All Life!

Apr 27 – May 4

$123 per night

Show all

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 free parking, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, 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.

Vacation rentals in Woodbury

Top-rated vacation rentals in Woodbury

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Woodbury vacation rentals

Stay near Woodbury's top sights

Other great vacation rentals in Woodbury

Home in Woodbury

Cottage in Southbury

Cottage in Bethlehem

Home in Woodbury

Home in Waterbury

Guesthouse in Southbury

Vacation home in Woodbury

Apartment in Bethlehem

Quick stats about vacation rentals in Woodbury

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

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

Are there family-friendly vacation rentals in Woodbury?

Are there vacation rentals with a dedicated workspace in Woodbury?

Do house rentals in Woodbury have a kitchen?

Do house rentals in Woodbury have air conditioning?

Do house rentals in Woodbury have wifi?

Are there pet-friendly vacation rentals in Woodbury?

Do house rentals in Woodbury have free parking?

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