Vacation rentals in Southbury

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Top-rated vacation rentals in Southbury

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

Guest favorite

Home in Brookfield

4.98 out of 5 average rating, 120 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

Nov 26 – Dec 3

G$78,354 GYD per night
Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 265 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).

Apr 4 – 11

G$32,436 GYD per night
Guest favorite

Home in Danbury

4.99 out of 5 average rating, 335 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

Nov 15 – 22

G$30,846 GYD per night

Popular amenities for Southbury vacation rentals

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 vacation rentals in Southbury

Guest favorite

Guesthouse in Newtown

4.78 out of 5 average rating, 18 reviews

Cozy & Convenient Stay in Newtown

Apr 6 – 13

G$20,816 GYD per night
Guest favorite

Apartment in Southbury

4.87 out of 5 average rating, 87 reviews

Suite Hill studio

Sep 12 – 19

G$29,405 GYD per night
Guest favorite

Apartment in Middlebury

4.98 out of 5 average rating, 61 reviews

Cozy Apartment with Water View of Brook

Nov 13 – 20

G$21,465 GYD per night
Guest favorite

Guesthouse in Newtown

5.0 out of 5 average rating, 43 reviews

Farm Cottage

Jun 8 – 15

G$37,461 GYD per night
Guest favorite

Apartment in Waterbury

4.98 out of 5 average rating, 64 reviews

Everything you need! Apartment!

Jan 14 – 21

G$23,392 GYD per night
Guest favorite

Home in Waterbury

4.9 out of 5 average rating, 31 reviews

Come and enjoy the BURY's of CT!

May 31 – Jun 7

G$39,169 GYD per night
Guest favorite

Guesthouse in Southbury

4.96 out of 5 average rating, 51 reviews

The Nest. Large studio in the Woods.

Nov 15 – 22

G$32,541 GYD per night
Guest favorite

Place to stay in Southbury

4.87 out of 5 average rating, 15 reviews

Cozy cute Relaxing home

Jan 26 – Feb 2

G$35,705 GYD per night
Guest favorite

Cottage in Bethel

5.0 out of 5 average rating, 55 reviews

The Sweet Retreat near Bethel & Newtown, King Bed

Apr 7 – 14

G$30,328 GYD per night
Guest favorite

Home in Southbury

4.83 out of 5 average rating, 23 reviews

Private & Peaceful Lakefront Home Beautiful View

Jan 21 – 28

G$104,514 GYD per night
Guest favorite

Loft in Woodbury

5.0 out of 5 average rating, 30 reviews

Country Loft

Nov 28 – Dec 5

G$30,575 GYD per night
Guest favorite

Home in Southbury

4.94 out of 5 average rating, 35 reviews

Cozy Nature Retreat at Chateau Madeux

Apr 23 – 30

G$69,649 GYD per night

Quick stats about vacation rentals in Southbury

Total rentals

40 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

1.6K reviews

Nightly prices starting at

G$4,189 GYD before taxes and fees

Frequently Asked Questions

  • Do house rentals in Southbury have wireless internet?

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

  • Do house rentals in Southbury have air conditioning?

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

  • How much does it cost to stay in house rentals in Southbury?

    Experience the best of Southbury with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Southbury?

    Yes! Work meets play with ease at over 10 vacation rentals in Southbury featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Southbury?

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

  • Are there family-friendly vacation rentals in Southbury?

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

Destinations to explore