
House holiday rentals in Southbury
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Top-rated house rentals in Southbury
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Popular amenities for house rentals in Southbury
House rentals with a pool

2 homes in one (in-law design) w/salt water pool
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!

The Getaway-HOST & Co.
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.

Amazing Oasis Private Pool, BBQ, Pool Table.
Glenda was friendly and had great communication from Start to Finish. This was a nice location for a family fun weekend. Although the drive is close enough to stores if you need anything (target/stopnshop/bjs etc), the property is in a quiet and safe neighborhood. The yard is a great place to hang out and relax with the fire pit or have fun in the pool. And when the weather was crappy the pool table and hanging out in the basement den was nice. Everything in the house is labeled and easy to find. We enjoyed the space and would definitely recommend. Thanks again! 😊

4Br Mountain Brook House on 130 acres w/ trails
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

Midcentury Modern ZenHouse Sculptor Studio
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.

Secluded Farmhouse - Studio Apartment Style Unit
Would recommend to anyone who wanted a clean and near the vineyards stay.

Meeker Hill House - Country Escape w/ Heated Pool
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!
Weekly house rentals

The Getaway: Beautiful Waterfront - New Milford CT
Enjoyed our stay in the woods with a beautiful view of the river. Easy to get to and very close to the charming town of New Milford and many good restaurants. Although right off a busy road it was quiet inside the house. The great room, which is on the top floor, is wonderful and perfect for both working and entertaining and has a full bath. It looks like the photos with an amazing view. The bedrooms and another bath are underneath. The master bedroom is the best. Just be aware you can hear the footsteps from above and not all of the bedroom windows have bug screens. The entertainment room on the lower level which opens into the yard is filled with games and a large tv and was lots of fun. The weather was cool & rainy so we didn’t use the outdoor space as much as we thought we would but there was a kayak. The house was private and although there is no interior deadbolt we felt safe. The house was clean with good heat/ac and wi fi. Hosts were responsive.

OWL's PERCH Candlewood Lakefront Rustic Cottage!
If you're looking for a cute little cottage in the woods near the lake to recharge and relax - this is it! KC provided an extensive list of instructions and to know's, which made check in/check out and all the in-between fool proof. KC was super friendly and responsive as well!

Lakeview Estate - Chef's Kitchen - NYC Getaway
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!

Artist's Retreat In The Woods | Five-Acre Backyard
What a fabulous home! My family had a peaceful and enjoyable stay at this hidden gem! The home is spotless and has everything you need to feel at home, sleep well and cook! Thank you to a superb host!!

A nestled retreat on 15 acres
We loved this house, it's beautiful inside and out. We watched deer in the early morning and had a dozen or more flowering trees dotting our view. The house is immaculate, and the kitchen is a dream for prepping and cooking. We were able to visit Yale, ocean beaches, wonderful restaurants, and ran into two farmers markets full with welcoming artists.. we had a rainy evening and enjoyed listening to the rain while we read. It's a great location if you want to do a Gilmore Girls weekend. If you know, you know. Thank you Kathleen for sharing your home.

Nature lover’s retreat in NWCT, breathtaking views
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!

Mid-Mod 2BR Cottage in CT Woods
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.

Comfortable home away from home
Terry and Jack’s place was perfect for us staying in Newtown visiting friends but we could also drive to Manhattan for day trips. House had everything you’d need and they even helped us get a crib delivered early/picked up later after we left. Super nice and responsive hosts! Will definitely stay again!
Private house rentals

Adorable Beach House on LI Sound
There’s so much to love about this charming open plan beach cottage! We especially enjoyed the water views, hearing the birds, and eating on the breezy porch. It was sparkling clean and stocked with everything you’d need, from comfortable beds and towels to many thoughtful essentials like hand and dish soaps, tea and coffee pods, paper towels/toilet paper, and shampoo/conditioner. Eileen is a gracious and responsive host — she was particularly understanding when we had to reschedule our visit. Thank you for a wonderful stay, Eileen, and we hope to return!

Don’t miss out on this cozy escape! w/Skatepark
Shawn created a special place here. Love all the details, especially the skateboards and music room. The hot tub was lovely after a long day of driving, I soaked again in the morning. ColecoVision console in the game room was so nostalgic along with a great selection of other games. I really enjoyed the grounds. Even wandered down to the dam/waterfall. My mother in law, son and wife all had their own space to stretch out. I could easily spend more time here, it is not just a place to lay your head for the night.

The Wildflower House
Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!

The Art House: 5-Acre Getaway w/ AC & Firepit
My family and I stayed at this Airbnb during my wedding weekend and it was perfect! The house is beautiful. It had one bedroom and bath downstairs for my grandma to stay in so she didn’t need to go up the stairs. The kitchen is amazing! It was a great distance to the Candlewood Inn where we got married. Jessica was very responsive and always checking in. Would definitely stay here again!

Private Woodland Sanctuary—3 mins to a lake beach!
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.

Hilltop Retreat- Lakefront with Dock
Our stay included spending family time in front of the fireplace watching Disney shows and with time spent enjoying meals around the cozy kitchen table. Enjoyed our stay very much and hope to go back one day

Charming Relaxing Raised Ranch
Incredibly clean, well stocked, private, and in the perfect location. You can enjoy the home with its large back yard and beautiful sunroom, or go walk to the restaurants that are right around the corner. Beth’s place has everything for a perfect stay. 1000% recommend staying here.

Mid-Century Modern House - Ciela Haus
Beautiful and tranquil home. Perfect for hosting family and friend that were in town for graduation. Thank you for a lovely stay.
Quick stats about house rentals in Southbury
Total rentals
10 properties
Nightly prices starting at
₹7,789 before taxes and fees
Total number of reviews
750 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
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- Pet-friendly rentals Southbury
- Rentals with lake access Southbury
- Rentals with a firepit Southbury
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- Fairfield Beach
- Yale University
- Rye Beach
- Rye Playland Beach
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Rye Town Beach
- Seaside Beach
- Jennings Beach
- Silver Sands Beach
- Bushnell Park
- Taconic State Park
- Quotonset Beach
- Sunken Meadow State Park
- Catamount Mountain Ski Resort
- Calf Pasture Beach
- Centerport Beach
- Kent Falls State Park
- Rockland Lake State Park
- Wildemere Beach
- Cedar Beach