Holiday houses in Watertown

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!

4.93 out of 5 average rating, 142 reviews

Guest suite in Cheshire

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

4.98 out of 5 average rating, 106 reviews

Cottage in Bethlehem

Cozy Getaway | Pet Friendly | Litchfield Cty

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

4.99 out of 5 average rating, 159 reviews

Apartment in Litchfield

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

4.92 out of 5 average rating, 185 reviews

Home in Bristol

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

4.97 out of 5 average rating, 120 reviews

Apartment in Litchfield

The Litchfield Nook - Cozy Uptown Apartment

Welcome to a cozy and peaceful nook in the hills! This well appointed apartment provides a home away from home feel. The unit is located on the first floor of a multi unit family house and sleeps 4 comfortably. You will be within walking distance to the iconic Litchfield Green and White Memorial Foundation. Everything that there is to see and do in Litchfield is within a short driving distance. Enjoy the beauty of Litchfield and come join us as our guest!

4.97 out of 5 average rating, 297 reviews

Home in Bethlehem

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.

4.95 out of 5 average rating, 193 reviews

Apartment in New Britain

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

4.94 out of 5 average rating, 250 reviews

Apartment in Bethlehem

Cozy 2nd Floor Suite In Bethlehem CT

Our private 2nd floor suite is fully equipped and easy on the budget. Sleeps a single or couple in comfort in queen bedroom. PLEASE NOTE- There is only one bed. This property is not suitable for friends traveling together unless they are willing to share the queen bed. Spacious living room and well-equipped kitchenette. Dedicated workspace. Relax with Wi-Fi, streaming channels. Free calls anywhere in the US.

4.92 out of 5 average rating, 121 reviews

Apartment in Middlebury

Cozy Apartment with Water View of Brook

Lower Level Beautiful Space: Well kept with an amazing view of a Beautiful Brook that Runs through the Backyard. It is a small cottage style home and you will have the best views of the Brook. You will also hear and see the Brook from the Bedroom, Kitchenette and Patio. Depending on the season it will Vary. If you have 2 Cars please make sure you let me know so I can accommodate.

4.89 out of 5 average rating, 105 reviews

Apartment in Winsted

Haven at Highland lake

Kick back and relax in this calm, stylish space. This studio apartment offers fast internet, TV , a comfortable couch , a stylish new bathroom, a lovely kitchenette, as well as black out curtains in the bedroom. And a cozy warm fireplace. This apartment comfortably sleeps 1 adult or a couple. The couch folds out into a bed and there is bedding in a tote stored Under the bed.

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Other great holiday rentals in Watertown

5 out of 5 average rating, 44 reviews

Barn in Roxbury

Fully Renovated Rural Barn

XenaRating, 5 stars3 weeks ago

My sister and I stayed at Kevin and Mina’s beautiful barn for 5 days. It was the perfect home base as we traveled through the neighboring towns on the Gilmore Girls trail. The house itself was specious, clean, well-decorated, and comfortable. It was great having the flexibility of enjoying the natural sunlight with the skylights open during the day and being able to sleep in a little with them closed overnight. Would definitely stay here again!

4.9 out of 5 average rating, 31 reviews

Apartment in Watertown

Steele Brook Manor

ColetteRating, 5 stars3 weeks ago

Very quaint typical New England home. We absolutely loved it and will be returning on a regular basis next year as it’s very convenient for us with our daughter at the local boarding school. Clean, tidy, free of clutter and very comfy. Good delivery service available from local restaurants if you don’t feel like going out. We were exhausted after packing up our daughters dorm room and just wanted to stay in. It felt like a home away from home .

4.76 out of 5 average rating, 42 reviews

Farm stay in Bethlehem

The Loft @ Sun One Organic Farm

WilliamRating, 5 stars3 weeks ago

This stay was nothing short of incredible. From the moment we arrived, we were blown away by the beauty and uniqueness of the property. The space is immaculately maintained, stylish, and comfortable, with every detail thoughtfully considered. The loft was a standout room—such a cool and unique design that added to the whole experience. Waking up to those stunning views each morning was a dream, and the peaceful, secluded atmosphere made it the perfect escape. The host was communicative, kind, and made everything seamless from start to finish. I can’t recommend this place enough. It exceeded all expectations and made for an unforgettable weekend. Will absolutely be returning to see the other units!

4.97 out of 5 average rating, 35 reviews

Guest suite in Watertown

Hidden Serenity at TuKasa - Pool & Billiards

AmraRating, 5 stars2 weeks ago

The host was so friendly! The place was extremely clean and very well decorated! We absolutely loved all the decorations especially all the cows :) the host responded so so quickly and was extremely helpful! We will definitely be coming back!!!

4.93 out of 5 average rating, 61 reviews

Guest suite in Plymouth

Secluded | Cozy | Nature

ChaiseRating, 5 stars1 month ago

Needed a place to stay for a wedding nearby. The space was really cute and located in a quiet neighborhood. Host was really kind and accommodating!

4.92 out of 5 average rating, 24 reviews

Home in Watertown

Historic Litchfield County Home

CarterRating, 5 stars1 month ago

Yverose was wonderful. We couldn't have asked for a better spot to host our weekend get together. The house was beautiful and so comfortable - perfect for 6 girlfriends. We would love to be back one day!!

5 out of 5 average rating, 73 reviews

Guest suite in Watertown

Private King suite w/ separate entry-Walk to Taft!

DeniseRating, 5 stars3 weeks ago

Easy to find when I figured out the gravel driveway. Every detail was considered, even the small items. Hosts very responsive when I needed something. This is the PERFECT location for Taft parents.