Family-friendly holiday rentals in Enfield

4.98 out of 5 average rating, 208 reviews

A bright bedroom features a queen size bed with light linens and decorative pillows. A small desk and chair are positioned beside the bed. A closet offers hanging space, and a floral artwork adorns the wall, adding a touch of color to the space.

Guest suite in Vernon

Laura's Loft and Gallery, private suite

Unique and roomy space with private entrance, two bedrooms, full bath with tub shower, and plenty of room to relax. Kitchen space has mini fridge, microwave, toaster oven, hot plate, and crock pot. Pleasant living area opening to 2nd floor deck. WiFi with Ethernet also, great remote work space. Quiet and private, only common area shared with us is first floor entry into breezeway. Free parking on premises. Full coffee setup for your breakfast included, and homemade scones in seasonal flavors.

5 out of 5 average rating, 160 reviews

A light-filled living area features a cozy sofa and elegant chairs arranged around a delicate coffee table. A decorative fireplace serves as a focal point, complemented by soft curtains and a tasteful chandelier. An ornate mirror reflects the natural light streaming through the large windows.

Guest suite in Enfield

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

Oversized 1800sf apartment is a 2-story unit, front half of a 200-year-old former schoolhouse in Enfield's historic district. The antique colonial is set up as a side-by-side duplex with private apartment occupying the front 1/2 of house & the owner's unit in the back with a separate driveway entrance & door. EXTRAS: ❋ PRIVATE USE OF POOL & PATIO ❋ KEYCODE CHECK-IN ANYTIME ❋ COFFEE/TEA BAR WITH EVERYTHING NEEDED ❋ POPCORN MACHINE, SNACKS & DRINKS ❋ 4 TVs: YOUTUBE TV, MAX, NETFLIX, WIFI

4.84 out of 5 average rating, 179 reviews

A bright workspace features a wooden desk with a black chair, positioned against a light-colored wall. Two framed botanical prints are displayed above the desk, complemented by a standing lamp. A mirror reflects the scene, while a potted plant adds a touch of greenery.

Flat in Windsor Locks

Apt near Big E, Six Flags, Bradley airport

Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Campervan/Motorhome in Wilbraham

A cozy seating area is featured, combining a spacious blue sofa and a comfortable beige armchair. Soft lighting and decorative pillows enhance the inviting atmosphere. Large windows provide views of the green outdoor landscape, while a patterned rug adds warmth to the space.

4.96 out of 5 average rating, 247 reviews

The Waddle on Inn

Welcome to The Waddle On Inn! Unique small farm experience meets luxury glamping and a serene paradise. We have created a farm getaway with a luxury 5th wheel with all the familiar comforts of home including wifi, smart TV, a screened in pavilion for you to enjoy your meals, our hilarious flock of ducks and goats for your entertainment! There are even fresh duck eggs for purchase as a take home souvenir! Relax, unwind, and Waddle On Inn! *Sunday check in time is 5pm all other days is 4pm*

4.98 out of 5 average rating, 132 reviews

A comfortable studio space is highlighted by a plush queen bed adorned with white bedding, positioned beside a cozy fireplace. Soft light is provided by a bedside lamp, while a fan offers air circulation. Neutral tones and warm accents create a welcoming ambiance.

Flat in Wilbraham

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Guest suite in East Granby

A brick patio area is seen with two rocking chairs positioned beside vibrant orange and yellow flower pots. A welcoming wreath adorns the double doors, and a pumpkin is placed on the ground, enhancing the seasonal decor.

4.85 out of 5 average rating, 392 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

4.96 out of 5 average rating, 219 reviews

Guest suite in Mansfield

Cozy private apt 8 mins from UCONN - solar powered

Relax & unwind in this amply sized private studio suite, complete with large seating/tv area & study/desk space. Space comes w/ 2 beds (1 queen, 1 full sized pull out futon couch) a full private bath, mini-fridge, cooktop, microwave, dishware, & utensils. Beautiful rural wooded area with numerous hiking trails nearby. Longer term rentals may be considered starting from Summer of 2025

4.92 out of 5 average rating, 485 reviews

The treehouse is elevated on wooden stilts, surrounded by vibrant autumn foliage. Large windows reflect warm light, showcasing a rustic wooden exterior. A staircase leads up to the entrance, inviting guests to explore this serene retreat among the trees.

Treehouse in Willington

Treehouse - Countryside - Farm Animals - Fire Pit

4.99 out of 5 average rating, 282 reviews

A bright living area features a dark sofa with multiple cushions, flanked by two patterned chairs. A wooden coffee table is positioned in the center, and a laptop is placed on it. Natural light enters through the two windows, adorned with dark curtains.

Flat in Enfield

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

4.95 out of 5 average rating, 248 reviews

A spacious living area is presented with a comfortable sofa adorned with patterned cushions. A central coffee table is visible, complementing the wood flooring. In the background, a kitchen area is equipped with essential appliances, featuring wooden cabinets and natural light from nearby windows.

Guest suite in Tolland

The Carriage House

Nestled in the woods, this secluded lower guest suite offers everything you will need for a relaxing stay. A very easy 20 minutes to Hartford or a quick 15 to UCONN. Private, full kitchen, bathroom, and laundry. Free level 2 EV car charging. Tons of space, a sunny deck and private entry. Ideal for a quick weekend or an extended stay.

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, 515 reviews

Flamig Farm Staycation

Very charming private farmhouse tastefully decorated situated in rural West Simsbury CT. Learn every day farm life from helping gather the 200 eggs daily and morning chores of caring for and feeding the petting zoo animals.

4.88 out of 5 average rating, 280 reviews

Home in Enfield

Scenic River View

Newly renovated home, quiet with scenic view of the Connecticut River. Light and airy, with a coastal theme throughout the home. Design to promote the relaxation and serenity that you need.

Popular amenities for Enfield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 109 reviews

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Villa in Columbia

Breathtaking home with unforgettable views & pool!

4.99 out of 5 average rating, 145 reviews

A cozy fire pit is surrounded by two black Adirondack chairs, positioned on a stone patio. The scene includes a snowy riverside landscape, with tree trunks and a gentle reflection of water in the background. A hanging pot adds a touch of greenery to the setting.

Cottage in Burlington

Cozy Lakefront Cottage w/Swim Spa & Firepit

4.99 out of 5 average rating, 135 reviews

The exterior of a lakefront cottage is illuminated by warm lighting at dusk. The structure features a vaulted roof with large windows, surrounded by trees. A deck extends around the cottage, reflecting on the calm water, creating a serene and inviting atmosphere.

Home in Coventry

Cozy cottage 5 minutes from UConn

4.93 out of 5 average rating, 537 reviews

A charming property is illuminated with colorful lights during the evening. The spacious deck is adorned with festive decorations, and a Christmas tree can be seen through large windows. The surrounding area is dark, emphasizing the warm glow of the lights.

Bungalow in Easthampton

The Creation Station

4.99 out of 5 average rating, 166 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

4.93 out of 5 average rating, 258 reviews

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

Romantic Getaway at The Lake!

4.98 out of 5 average rating, 132 reviews

An outdoor fire pit is surrounded by several adirondack chairs on a grassy area. A stone wall frames the fire pit, with trees and a glimpse of a secondary building in the background. The scene reflects a serene natural setting.

Cottage in Bethlehem

Cozy Getaway | Pet Friendly | Litchfield Cty

4.99 out of 5 average rating, 135 reviews

A hot tub with bubbling water is showcased under a covered patio, offering a view of the serene lake and surrounding trees. Soft lighting enhances the tranquil setting, while glimpses of the lake's shoreline and distant boats are visible in the background.

Cottage in Southwick

Foliage Lake Views from Hot Tub, Fire Pit & Kayaks

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 249 reviews

A panoramic view of the expansive farmland stretches towards a distant mountain range under a colorful twilight sky. Two wooden chairs are positioned on the grassy area, providing a serene spot to enjoy the landscape.

Tiny home in Northampton

Tiny House Farm Retreat: Mountain Views, Fire pit

4.86 out of 5 average rating, 155 reviews

A red barn-style building with large windows is shown against a clear blue sky. The surrounding area is covered with snow, highlighting the building's architecture. Shadows from nearby trees fall gently on the ground, creating a peaceful winter scene.

Guest suite in Windsor

Rustic Loft Apartment

4.96 out of 5 average rating, 108 reviews

The open living space features a kitchen island with a granite countertop and wooden cabinetry. A dining set with high chairs is positioned nearby. A comfortable blue sofa and a television stand are visible in the living area, complemented by hardwood flooring throughout.

Flat in Manchester

Your home away from home for Comfort & Convenience

4.89 out of 5 average rating, 167 reviews

A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.

Home in South Windsor

Spacious 3 Bedroom Ranch With Office

Guest suite in Bloomfield

The bedroom features a spacious bed with white bedding, complemented by a wooden desk and chair. Two windows with light-filtering shades allow natural light to enter, while a world map adorns the walls. Built-in storage and warm hardwood flooring add to the room's charm.

4.92 out of 5 average rating, 115 reviews

Private Cozy Suite, 0 Fees, Easy CheckIn, EV Plug

4.9 out of 5 average rating, 164 reviews

A welcoming exterior features a curved brick pathway leading to a front porch surrounded by neatly trimmed evergreen shrubs. Potted plants add color to the entrance, complemented by decorative hanging baskets. The home presents a classic facade with white columns framing the entrance.

Flat in Suffield

2 BR LR 1BA Private In-Law Suite with Home Theater

4.88 out of 5 average rating, 227 reviews

The exterior of a charming red schoolhouse and accessory building is surrounded by vibrant foliage. A white wooden fence outlines the property, leading to a gravel pathway. The buildings feature classic architectural details, with windows framed in white and a backdrop of lush trees.

Cottage in Granby

The Little Red Schoolhouse ~ Circa 1877

Guest suite in Coventry Lake

A cozy living space is presented, featuring a blue couch, a small wooden dining table with four chairs, and access to a bedroom and kitchen. Natural light enters through multiple windows, while neutral walls and beige carpet enhance the inviting atmosphere.

4.91 out of 5 average rating, 312 reviews

Country retreat 25min to Hartford/15min to UCONN

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 360 reviews

A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.

Guest house in Southbury

Charming Guest Cottage with Modern Amenities

4.9 out of 5 average rating, 177 reviews

Villa in Norwich

Private Villa, Pool, New King Bed, close to casino

4.98 out of 5 average rating, 163 reviews

A living area features a comfortable sofa and two armchairs, arranged around a rustic coffee table. A fireplace is set into a stone mantel, and a large television is mounted on the wall. Sliding doors lead to a private balcony, allowing natural light to fill the space.

Apartment in Norwich

The Vacay Villa

4.99 out of 5 average rating, 213 reviews

A spacious bed is adorned with a plush, white comforter and decorative pillows, including one reading 'home.' A tray with refreshments and a poolside bag rests nearby. Soft lighting from bedside lamps enhances the room's calm ambiance, complemented by a framed landscape photograph on the wall.

Apartment in Norwich

Peaceful Oasis steps from Mohegan Sun

4.96 out of 5 average rating, 119 reviews

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Flat in Otis

Enjoy every season the Berkshires have to offer.

4.93 out of 5 average rating, 197 reviews

A cozy living room features exposed wooden beams and warm wood-paneled walls. A stone fireplace is centrally located, with a basket of wood beside it. A rug with rich colors lays under a wooden table, surrounded by comfortable seating, inviting a relaxed atmosphere.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

4.89 out of 5 average rating, 448 reviews

An open living space showcases a wooden table with candles, surrounded by wooden chairs. A white sofa with decorative cushions is positioned next to a reddish armchair. A coffee table sits central, with a small plant atop a patterned rug. Light illuminates the cozy atmosphere.

Flat in Glastonbury

Quiet 2 bed room apt w/ private entrance.