Holiday rentals in Southbury

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Top-rated holiday rentals in Southbury

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Guest favourite

Guest house 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).

22–29 Sep

$211 SGD per night

Guest favourite

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Private 1100 sq. Ft. suite staycation located in a beautiful, safe, quiet neighborhood in DanburyModern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with Cable/Amazon Prime/Netflix, Apple Cable charger next to bed, Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking inside and outside the premises including vaping. No children or infants

2–9 Jan

$207 SGD per night

Guest favourite

Guest house in Newtown

4.78 out of 5 average rating, 18 reviews

Cozy Stay in Newtown - discounts for long term

1 Bed Room 1 Bath Apartment (shared wall) close to the quaint Sandy Hook Village, filled with restaurants, a wine bar, brewery, vineyard, boutiques, cafés, and beautiful scenery with walking trails. Easy access to exit 10 84. Plenty of natural light. Peaceful and quiet neighborhood perfect for a get away or work trip. This is a residential apartment - no shared entrances or access to space from main house, but it is a shared property. Stays longer than 31 days, inquire for discounted rate.

2–9 Dec

$154 SGD per night

Guest favourite

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!

2–9 Aug

$98 SGD per night

Guest favourite

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."

1–8 Dec

$401 SGD per night

Guest favourite

Guest suite in Bethlehem

4.99 out of 5 average rating, 197 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.

27 Jul – 3 Aug

$254 SGD per night

Guest favourite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

2–9 May

$201 SGD per night

Guest favourite

Flat in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

21–28 Feb

$195 SGD per night

Guest favourite

Flat in Brookfield

4.94 out of 5 average rating, 183 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.

12–19 Mar

$167 SGD per night

Guest favourite

Flat in Southbury

4.87 out of 5 average rating, 87 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.

18–25 Aug

$190 SGD per night

Guest favourite

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.

24–31 Mar

$128 SGD per night

Guest favourite

Home in Southbury

5.0 out of 5 average rating, 54 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.

12–19 Aug

$219 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Southbury holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Southbury's top sights

Aquila's Nest Vineyards14 locals recommend

Riverview Cinemas8 locals recommend

Maggie McFly's® Southbury3 locals recommend

ShopRite of Southbury11 locals recommend

Laurel Diner7 locals recommend

Stop & Shop7 locals recommend

Other great holiday rentals in Southbury

Guest favourite

Flat in Middlebury

4.98 out of 5 average rating, 64 reviews

Cozy Apartment with Water View of Brook

1–8 Oct

$140 SGD per night

Guest favourite

Flat in Waterbury

4.98 out of 5 average rating, 65 reviews

Everything you need! Apartment!

23 Feb – 2 Mar

$158 SGD per night

Guest favourite

Guest house in Southbury

4.96 out of 5 average rating, 51 reviews

The Nest. Large studio in the Woods.

26 Feb – 5 Mar

$218 SGD per night

Guest favourite

Cottage in Bethel

5.0 out of 5 average rating, 57 reviews

The Sweet Retreat near Bethel & Newtown, King Bed

16–23 Apr

$190 SGD per night

Guest favourite

Home in Waterbury

4.91 out of 5 average rating, 32 reviews

Come and enjoy the BURY's of CT!

1–8 Mar

$255 SGD per night

Guest favourite

Loft in Woodbury

5.0 out of 5 average rating, 31 reviews

Country Loft

23–30 Oct

$199 SGD per night

Guest favourite

Cottage in Newtown

4.95 out of 5 average rating, 58 reviews

Private Country Cottage

2–9 Jul

$200 SGD per night

Guest favourite

Flat in Bethel

4.9 out of 5 average rating, 89 reviews

Spacious Bethel Home Close to Downtown

2–9 Jan

$192 SGD per night

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Quick stats about holiday rentals in Southbury

Total rentals	30 properties
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	1.7K reviews
Nightly prices starting at	$27 SGD before taxes and fees

Holiday rentals in Southbury

Top-rated holiday rentals in Southbury

Guest house in Southbury

Home in Danbury

Guest house in Newtown

Guest suite in Watertown

Home in Woodbury

Guest suite in Bethlehem

Cottage in Easton

Flat in Redding

Flat in Brookfield

Flat in Southbury

Guest suite in Morris

Home in Southbury

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Southbury holiday rentals

Stay near Southbury's top sights

Other great holiday rentals in Southbury

Flat in Middlebury

Flat in Waterbury

Guest house in Southbury

Cottage in Bethel

Home in Waterbury

Loft in Woodbury

Cottage in Newtown

Flat in Bethel

Quick stats about holiday rentals in Southbury

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore