Holiday houses in Southbury

4.94 out of 5 average rating, 324 reviews

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).

5 out of 5 average rating, 25 reviews

Apartment in Southbury

New Apartment Centrally Located in Southbury

Keep it simple at this peaceful and centrally-located apartment. Recently renovated with all the essential amenities to make your stay just like home. Wi-Fi, washer, dryer, cooktop, fridge, oven, microwave, toaster, smart TV and Keurig are ready to make your stay pleasant. An outdoor porch is available for dining in warmer months. It includes one new queen bed plus sofa bed for one adult or two kids. Located just minutes from shopping and dining in downtown Southbury with easy access to 84

4.91 out of 5 average rating, 196 reviews

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!

4.99 out of 5 average rating, 301 reviews

Guest suite in Bethlehem

Breezy Crest cozy, private retreat near Litchfield

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 summer fun!

4.89 out of 5 average rating, 37 reviews

Guesthouse in Watertown

Private studio guesthouse

Kick back and relax in this peaceful, quiet, stylish space with high ceilings, central heat and air, huge bathroom, mini kitchen, fridge, microwave, coffee maker, 75" TV, onsite laundry and workout equipment when needed, private parking space, private entrance, high-speed internet, countless local restaurants, fast food chains and cafes, all major supermarkets, hospitals and doctors offices, post offices, easy access to numerous lakes, golf course and wineries. Indeed, a home away from home.

5 out of 5 average rating, 45 reviews

Barn in Roxbury

Fully Renovated Rural Barn

Newly renovated barn on a quiet rural road yet close to all the attractions of Southern Litchfield County. The light-filled barn has two large patio doors into a substantial living and entertaining area with a large sectional sofa-bed, a dining table for 10 and adjacent kitchen area with an island. There is a downstairs washroom. A large light-filled upstairs sleeping area has a king-size bed and a bathroom with shower. Outside is a patio dining area and parking in a dedicated driveway.

Superhost

Farm stay in Bethlehem

4.75 out of 5 average rating, 44 reviews

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, that a a separate entrance. The loft has a desk and great WIFI service. Next to the loft is our another Airbnb, Our Silo, which is available for rent.

4.77 out of 5 average rating, 26 reviews

Apartment in Monroe

Charming 1-Bedroom duplex apartment in Monroe

Welcome to Your Home Away from Home! Escape to our cozy 1-bedroom apartment nestled in a private setting in Monroe. Perfect for couples, solo travelers, or small families, this tranquil retreat offers all the comforts you need for a relaxing stay: Spacious Bedroom, Fully Equipped Kitchen, Private Entrance, Outdoor Area, Free Wi-Fi. Situated in a quiet neighborhood, our apartment is just a short drive from local attractions, Trumbull Mall, parks, restaurants and nearby hiking trails.

4.92 out of 5 average rating, 282 reviews

Apartment 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.

Superhost

Guesthouse in Southbury

4.93 out of 5 average rating, 71 reviews

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.

4.99 out of 5 average rating, 121 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. Please note that we allow pets (dogs only) and have a limit of two.

Apartment in Downtown New Haven

4.92 out of 5 average rating, 225 reviews

Stay @ the Roost on Mansfield in the heart of Yale

The Roost on Mansfield is a cozy and comfortable two bedroom apartment located in the heart of campus right across from the Yale Hockey Rink. The Roost has lots of sunlight, is fully furnished, has great amenities- free secure off-street parking, beddings, great cooking gear, everything you need as a guest. The building has exterior cameras, security monitoring and is equipped with digital locks for flexible check-in.

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Other great holiday rentals in Southbury

4.88 out of 5 average rating, 49 reviews

Cozy Nature Retreat at Chateau Madeux

Stacy Rating, 5 stars4 weeks ago

I shared two nights in this beautiful home with my family. Although I do not have a pet, the house was pet friendly with amenities for every singly family member and every age. The home was spacious and also had common room areas for smaller gatherings. The beds were extremely comfortable and the water pressure in the showers were excellent. Would definitely book again and recommend.

5 out of 5 average rating, 5 reviews

Waterfront 3 bedroom house

BlancaRating, 5 stars5 months ago

The lake house was spectacular. The view was beautiful. It does contain several stairs. However, has great lighting. Definitely renting in the summer to enjoy the lake. If you are looking for a peaceful beautiful place, this is it!

Private room in West Haven

4.93 out of 5 average rating, 183 reviews

Cozy bedroom near the beach.

JacquelineRating, 5 stars1 week ago

Excelent and beautiful house. The bedroom is beautiful, clean, big , great. Peaceful stay. Danny was very kind and helpful allowing me to park my car in a very safe parking in the backyard. Thank you!

4.82 out of 5 average rating, 33 reviews

Cozy cute Relaxing home

TylerRating, 5 stars1 week ago

The place is fantastic. The lake is very close. You can tell that the owners are always working to improve this place as well.

Guesthouse in Roxbury

4.75 out of 5 average rating, 4 reviews

Modern Country

Jennifer FlynnRating, 5 stars1 month ago

Stunning guesthouse in the rolling hills of NW CT. Well stocked, luxurious linens, privacy abounds with the comfort of friendly hosts. A perfect home away from home for regional exploring. Excellent hiking in the area, quaint shops, and farm to table dining. Recommend Hollister House Garden for self guided garden tours.

4.98 out of 5 average rating, 63 reviews

Guesthouse in Newtown

Guest Suite at Wisteria Gardens

PeterRating, 5 stars1 week ago

So peaceful, so comfortable and just the nicest hosts. And there are goats!! Just a perfect little place to spend a quiet night off the road. Beautifully tucked away off the beaten path and Christine is so nice and welcoming. She even had to-go coffee cups for our early morning departure. Very nice touch. Highly recommend!

Private room in New Milford

4.9 out of 5 average rating, 291 reviews

"The Parsonage" 1 or 2 Bdrm Suite with full bath

SamanthaRating, 5 stars4 days ago

Anne is a marvelous host, and her place is so quaint and cozy! We felt right at home. It’s such a peaceful spot and just a few minutes from the New Milford Town Greene with restaurants, cafes, etc. Our kids (toddler and infant) loved their stay as well! Hope to visit again soon!