Family-friendly holiday rentals in Waterbury

4.96 out of 5 average rating, 159 reviews

Home in Waterbury

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

Indoor spacesFamilyNearby

4.98 out of 5 average rating, 101 reviews

The historic home features a two-story structure with white siding and black shutters. A covered porch is highlighted at the front, surrounded by lush greenery and blooming flowers, set against a clear blue sky. A grassy lawn offers open space in the foreground.

Guest suite in Watertown

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

Enjoy Litchfield County, CT! This renovated 1-bedroom guest suite in an 1859 historic home has a private entrance off a dedicated covered porch. Enter through the private stairway into the bedroom with a King size bed and comfortable foam mattress. French doors open into a living room with a pullout full size sofa bed and a Nespresso coffee maker. The renovated bath has marble floors and a glass door shower. Free parking for up to two cars in the drive and directly across the street from Taft.

FamilyIndoor spacesWalkability

4.87 out of 5 average rating, 173 reviews

A comfortable living space is presented, combining a light-colored sofa and a larger grey sectional couch. A wooden coffee table sits centrally, with artwork displayed on the wall above. Soft lighting is provided by overhead fans, enhancing the cozy atmosphere.

Guest suite in Waterbury

Private cozy getaway

Take a break and unwind at this peaceful oasis. Separate entrance for privacy, queen bed, pull out sofa, roll away cot, jacuzzi tub, extra large shower. Location is perfect, minutes from Hawks landing golf course, Post University, Brass mill mall, Metro north, Saint Mary and Waterbury hospital. **Please leave the house in the same condition! No bubbles or anything inside jacuzzi! **Septic system -Do not flush anything but toilet paper** NO Tampons, pads Paper towels Trash Baby wipes

Indoor spacesKitchenHeating

4.93 out of 5 average rating, 122 reviews

A spacious living area is presented with a large flat-screen TV mounted on a white entertainment unit. A soft gray sofa sits nearby, and a decorative area rug enhances the room's aesthetic. Natural light streams in through a front door adorned with a glass panel.

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.

KitchenFamilyQuiet

4.95 out of 5 average rating, 105 reviews

A cozy living room features a stone fireplace with a mounted television above. Natural light enters through a large window, accented by sheer curtains. A plush rug covers the floor, surrounded by a sectional sofa and a chair, offering a comfortable gathering space.

Home in Waterbury

Come and enjoy the BURY's of CT!

Welcome to your home away from home! Nestled in a charming, safe, and quiet neighborhood, our cozy retreat offers the perfect blend of comfort and convenience. You'll love the tree-lined streets and peaceful atmosphere—a perfect place to relax after a day of exploring. Whether you're here for business or leisure, our home provides a warm and welcoming space in a delightfully cute corner of town. Enjoy all that CT has to offer from the rolling hills of Litchfield to the waters of the sound.

Indoor spacesKitchenComfort

5 out of 5 average rating, 108 reviews

A newly renovated barn features a dark exterior with large windows on both levels. A gravel patio area is surrounded by low shrubs, providing a space with a table and chairs for outdoor dining. Lush green trees frame the serene setting.

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.

KitchenIndoor spacesLayout

4.97 out of 5 average rating, 107 reviews

Apartment in Southbury

Cozy 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, 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 i84

FamilyKitchenNearby

4.94 out of 5 average rating, 151 reviews

A wooden dock extends over calm lake waters, framed by vibrant hues of pink and purple in the sunset sky. Two adirondack chairs are positioned on the dock, inviting relaxation while enjoying the serene views, with softly glowing lanterns along the water's edge.

Cottage in Plymouth

Cozy Oasis, Lakefront with Stunning Sunset Views

It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits! Pet friendly!

Indoor spacesKitchenAccess

4.92 out of 5 average rating, 235 reviews

The exterior of a charming three-bedroom house is displayed, featuring a sloped roof and neatly trimmed bushes. A large tree provides shade in the front yard, while a stone pathway leads to the entrance. Side decorations include a swing and tree remnants.

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.

KitchenIndoor spacesTV

4.86 out of 5 average rating, 258 reviews

A comfortable living area features a sectional sofa adorned with colorful cushions, a small table, and a cozy throw blanket. Natural light enters through a window, illuminating the stone fireplace and surrounding furniture on a polished tile floor.

Guest suite in Waterbury

Waterbury Cozy, Private In-Law Suite

Cozy and private 1 bedroom apartment/ In-law suite in the basement of a private house with a separate entrance and parking right in front! Guests have the entire space to themselves. Why check-in to a hotel when you can make yourself at home with complimentary parking, WiFi, toiletries, coffee and an Amazon Fire TV Stick. Come enjoy your stay in a beautiful, spacious, sparkling clean, and comfortable apartment in a safe neighborhood.

Indoor spacesFamilyTV

4.94 out of 5 average rating, 166 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.

KitchenIndoor spacesAir conditioning

4.97 out of 5 average rating, 109 reviews

The living area features a large leather sectional sofa arranged around a wooden coffee table, with a cozy area rug beneath. Natural light pours in through multiple windows, highlighting the exposed log beams on the ceiling and the warm wooden walls.

Cabin in Harwinton

Beautiful Brook-side Log Cabin on 3 Private Acres

Fall asleep to the sound of the rushing brook in this beautifully restored log home. The cabin sits in the middle of three wooded acres overlooking Catlin Brook as it cascades through the gorge below. It seems like wilderness, yet all the amenities of Harwinton are just a few minutes away.

KitchenIndoor spacesHospitality

Popular amenities for Waterbury family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.83 out of 5 average rating, 117 reviews

The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.

Home in Litchfield

The Getaway-HOST & Co.

KitchenIndoor spacesHot tub

4.99 out of 5 average rating, 134 reviews

Home in Plymouth

Cozy escape w/private hot tub & backyard skatepark

FamilyIndoor spacesCheckout

4.98 out of 5 average rating, 189 reviews

A jetted swim spa is positioned on a deck overlooking Lake Garda at sunset. The water's surface reflects soft hues of orange and pink, with serene trees framing the view. The spa displays an illuminated edge, enhancing the tranquil atmosphere of the lakeside setting.

Cottage in Burlington

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

KitchenFamilyBreakfast

4.87 out of 5 average rating, 410 reviews

The charming cottage, with its white siding and red door accents, is set amidst lush greenery. A well-maintained yard features grass and flowering plants, while a stone wall frames the scene, adding to the property's rustic appeal.

Cottage in Litchfield

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

KitchenFamilyBackyard

4.99 out of 5 average rating, 186 reviews

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

Home in Vernon

Luxe Bolton Lake

KitchenFamilyAccuracy

4.95 out of 5 average rating, 238 reviews

The cabin is nestled among tall trees next to a flowing creek. Natural rock formations surround the water, creating a serene setting. Sunlight filters through the leaves, casting dappled shadows on the cabin's exterior, which features large windows that overlook the creek.

Cabin in New Milford

Creekside Cabin with Wood Fired Hot Tub & Firepit

Indoor spacesFamilyParks

4.99 out of 5 average rating, 168 reviews

The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.

Cottage in Bethlehem

Cozy Cottage |Quintessential CT | Pet Friendly

Indoor spacesKitchenLayout

4.99 out of 5 average rating, 248 reviews

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

FamilyIndoor spacesWi-Fi

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 351 reviews

A geodesic dome is situated amid a wooded area, featuring a shingled exterior and a green door with multiple panes. Surrounding stones create a natural base, and a mixture of bare trees and underbrush complements the serene setting.

Dome in Bethlehem

Geodesic Dome in the Wooods

Indoor spacesFamilyLaundry

4.84 out of 5 average rating, 119 reviews

A bright living area features a teal sofa paired with a light gray armchair, accented by a round coffee table at the center. Natural light floods in through large windows, with soft curtains enhancing the serene atmosphere. Art pieces adorn the walls, complementing the hardwood floor.

Home in Bristol

Stylish & Luxurious 3 BDR home with Play Station

Indoor spacesKitchenGetting around

4.88 out of 5 average rating, 150 reviews

The red yurt is set among tall trees, showcasing a spacious wooden deck surrounded by a lattice railing. Large windows allow natural light to enter, while the soft curves of the yurt blend harmoniously into the wooded landscape.

Yurt in Guilford

Hartwoods Yurt

FamilyIndoor spacesCleanliness

4.82 out of 5 average rating, 260 reviews

A rustic cabin with green log siding is surrounded by tall trees. The front porch features two black chairs, and a storage trunk adds a practical touch. A decorative star and wall clock enhance the inviting exterior, while a garden area complements the natural setting.

Bungalow in Trumbull

Cozy, romantic cabin by the lake.

KitchenFamilyBackyard

Farm stay in West Simsbury

A rustic farmhouse exterior showcases a wooden façade with red double doors and a welcoming balcony adorned with potted flowers. The balcony is accessed by wooden steps, leading to a charming outdoor seating area. Seasonal foliage decorates the surrounding landscape.

4.96 out of 5 average rating, 555 reviews

Flamig Farm Staycation

Indoor spacesFamilyCheck-in

4.95 out of 5 average rating, 118 reviews

A welcoming living room features a comfortable couch and two textured armchairs, arranged around a central round coffee table. Natural light filters through large windows, highlighting a cozy atmosphere. A small side table displays a plant and a soft throw blanket.

Home in New Britain

Bright & Private WHOLE HOUSE 4 YOU Near Everything

FamilyIndoor spacesDecor

4.98 out of 5 average rating, 175 reviews

A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.

Home in Southbury

The Cottage at Cedar Spring Farm

Indoor spacesKitchenValue

4.96 out of 5 average rating, 140 reviews

A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.

Cottage in Seymour

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

KitchenFamilyLayout

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 265 reviews

An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.

Barn in Bethel

Escape to a Restored New England Antique Milk Barn

KitchenFamilyCleanliness

4.95 out of 5 average rating, 208 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

Indoor spacesFamilyBarbecue

4.97 out of 5 average rating, 213 reviews

A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.

Guest suite in Monroe

Garden Level Suite with Beautiful Pool

FamilyIndoor spacesQuiet

5 out of 5 average rating, 187 reviews

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

KitchenIndoor spacesWalkability

4.98 out of 5 average rating, 159 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

Indoor spacesFamilyBackyard

4.93 out of 5 average rating, 212 reviews

A serene view of the pool is presented, framed by lush greenery and vibrant plant life. The clear water reflects the sky, while distant hills and a pond are visible at the horizon, creating a peaceful outdoor retreat.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

KitchenIndoor spacesLong stay

4.97 out of 5 average rating, 117 reviews

A spacious bedroom is presented with a comfortable bed, layered in plush white linens and accented with dark pillows. A wooden dresser sits in front of a large window, allowing natural light to fill the room, while art decorates the walls.

Apartment in New Haven

King 1BR W/ Parking, Pool & Gym

Indoor spacesFamilyTV