Family-friendly vacation rentals in Chicopee

Guest suite in Belchertown

A serene scene depicts several horses grazing in a fenced area, surrounded by vibrant autumn foliage. A charming white house is visible in the background, framed by trees under a clear blue sky. Natural light enhances the tranquil setting.

4.98 out of 5 average rating, 153 reviews

Serene 1-br suite on 75 acre horse property

Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

4.98 out of 5 average rating, 235 reviews

A serene sleeping area is present, featuring a spacious bed adorned with a patterned duvet. Large windows frame the view of the surrounding trees, inviting natural light into the space. A small bookshelf stands in the corner, complementing the wooden floors and walls.

Cabin in Cummington

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Apartment in Windsor Locks

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.

4.85 out of 5 average rating, 177 reviews

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

4.96 out of 5 average rating, 283 reviews

A spacious living area is furnished with a gray sectional sofa, accented with colorful throw pillows. A wooden coffee table is placed in front, on a soft area rug. Two large windows allow natural light to brighten the room, complemented by ceiling fans and tasteful decor.

Loft in Tolland

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

4.96 out of 5 average rating, 245 reviews

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.

Camper/RV in Wilbraham

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*

4.94 out of 5 average rating, 113 reviews

A warm, orange wall frames the sleeping area, featuring a spacious bed with neutral linens and decorative pillows. Soft light is provided by two bedside lamps, and a large window offers a glimpse of the outside while inviting natural light into the room.

Apartment in Northampton

Warm & Stylish Apartment w/laundry - walk to DT

Warm and stylish 1 bedroom apartment with private garden entrance located steps from downtown Northampton. Newly refinished with a comfortable queen bed, sleeper sectional and luxury linens. It has a fully functional kitchen, bathroom, living room with a flatscreen, Roku and high-speed wifi as well as a washer/dryer in the unit-- perfect for a staycation or for a relaxed homestay for your remote work. Walk 15 mins to restaurants downtown, 20 mins to Smith College and 2 to the bike path.

Tiny homes in Northampton

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.

4.98 out of 5 average rating, 244 reviews

Tiny House Farm Retreat: Mountain Views, Fire pit

The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

4.93 out of 5 average rating, 192 reviews

A welcoming living room features two comfortable sofas flanking a round coffee table. Natural light floods in through large windows with white curtains, illuminating the light-colored carpet and neutral walls. Decorative elements include simple wall art and a ceiling fan, creating a relaxed atmosphere.

Apartment in Holyoke

Spacious Apartment! Easy on & off of I-91 & I-90

Located off of Northampton St. this 2nd floor apartment is close to I-91, I-90 & 391 making for quick & easy travel! There is a beautiful park up the street including a playground, hiking trails and dog park. The Holyoke Mall is located nearby and there is a Walgreens 0.3 miles away. Free street parking. This apartment has one queen bed, two twin beds & a futon in the sun-room if needed for extra guests. This is a private apartment with kitchen, laundry and bathroom all to yourself!

4.93 out of 5 average rating, 179 reviews

The living area showcases polished hardwood flooring and large windows allowing natural light to fill the space. A modern coffee table sits prominently in the center, flanked by two black chairs and an orange lounge piece. A television is positioned against a wall.

Apartment in Chicopee

Bright and cozy 3 bedroom apartment in Chicopee

Your family will love this spacious, beautifully updated apartment with private access. A friendly, walkable neighborhood, just a block from Elms College Campus. Szot Park and Chicopee Center. A few blocks from Baystate Medical Center. Nine minutes from Downtown Springfield (MGM Casino, Basketball Hall of Fame, Dr. Seuss Museum, and more!). Within less than 30 minutes of Six Flags, Bradley Airport, Downtown Hartford. Less than 1 hour from the scenic Berkshires and so much more!

4.98 out of 5 average rating, 131 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.

Apartment 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.

4.89 out of 5 average rating, 1,001 reviews

A welcoming entrance features a maroon front door with glass panes, flanked by a wooden railing. A slight wooden ramp leads up to the door, surrounded by a manicured area of small plants and gravel, creating an inviting first impression.

Home in Feeding Hills

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

4.83 out of 5 average rating, 254 reviews

An organized living space features a spacious bed centered against the wall, accompanied by a dark sofa with decorative cushions. A media console holds a television, with built-in shelves displaying plants and framed art. Soft lighting enhances the warm wood flooring.

Guest suite in Holyoke

Lovely 1 Bedroom w private entrance

Ground floor apartment with private entrance and parking on a quiet circle road. The apartment includes a "mini kitchen" with microwave, small fridge with freezer, and some kitchen basics. The unit also includes a washer and dryer! Recently renovated private bathroom. Very centrally located, 15 mins from Downtown Northampton and Springfield, 20 minutes to Amherst, central to all area colleges, and 1 hour from the beauty of the Berkshires! All are welcome!

Popular amenities for Chicopee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 217 reviews

Guest suite in Mansfield

Cozy private apt 8 mins from UCONN - solar powered

Guest suite in Northampton

A spacious bedroom features a king bed dressed in dark bedding, flanked by windows with wooden shutters. A TV is mounted on the wall, and a small wooden cabinet offers additional storage. A chair and side table complement the minimalistic decor, creating a bright and airy ambiance.

4.91 out of 5 average rating, 108 reviews

Sweet suite, walk to town tout suite!

4.98 out of 5 average rating, 133 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, 535 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

4.97 out of 5 average rating, 116 reviews

A spacious living area features vaulted wood ceilings and a mix of natural wood and stone finishes. A comfortable couch and chair are arranged around a central coffee table, with a warm glow from the fireplace adding to the cozy ambiance. Light enters through large windows.

Cabin in Chesterfield

Hilltown Cabin Hideaway: A River Runs Through It!

4.88 out of 5 average rating, 659 reviews

A charming farmhouse is depicted, featuring a white exterior and a welcoming red front door. Windows provide natural light, and a wood pile is neatly stacked beside the entrance. Lush greenery and seasonal foliage surround the home, set against a clear blue sky.

Home in Northampton

The Farmhouse - Hot tub eclectic farmhouse 3 br

4.98 out of 5 average rating, 133 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

4.94 out of 5 average rating, 277 reviews

The exterior of a cozy guest house is presented, featuring a green facade and a welcoming entrance. A wooden deck with potted plants and decorative lights is accessible via stairs. Surrounding the house, lush greenery and garden features enhance the tranquil atmosphere.

Home in Northampton

Clean and sunny house near Smith College

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 117 reviews

The compact kitchen area features a bright red refrigerator and a vintage-style stove. Light blue cabinetry provides storage, while a white sink is positioned under a window overlooking the outside. Wooden floors add warmth to the space, with neatly arranged kitchen essentials visible.

Train in Palmer

Trainmaster's Inn - Caboose

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, 382 reviews

Staying at Ten Hillcrest

4.97 out of 5 average rating, 406 reviews

A bright living area features wooden flooring and a blend of seating options, including a yellow sofa and patterned armchairs. A glass coffee table sits atop a decorative rug, complemented by artwork on the walls and natural light streaming through the window.

Apartment in Northampton

Light filled three bedroom apartment DT Florence!

4.96 out of 5 average rating, 106 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.

Apartment in Manchester

Cozy 1 bedroom clean and quiet

4.88 out of 5 average rating, 246 reviews

The image showcases a spacious green yard surrounding a charming gazebo. In the foreground, assorted seating arrangements invite relaxation. The background features trees in full bloom, enhancing the natural setting and providing a peaceful atmosphere.

Home in Brimfield

Little House Inn - Brimmy - Private Home

Guesthouse in Northampton

The entrance features a white door with a windowpane design, framed by light blue siding. A decorative lantern hangs beside the door. A small potted plant rests on a blue chair, while a welcome mat adorned with black dogs is placed at the threshold.

4.99 out of 5 average rating, 381 reviews

Mill River Cottage (pet friendly!)

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, 309 reviews

Country retreat 25min to Hartford/15min to UCONN

Guest suite in South Windsor

A spacious outdoor area is showcased, featuring a well-maintained lawn and a wooden deck leading to a white, single-story house. Surrounded by trees, the private yard includes a white picket fence, providing a sense of seclusion.

4.85 out of 5 average rating, 211 reviews

Private Spacious Suite with Private entrance!

Family-friendly home rentals with a pool

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!

4.84 out of 5 average rating, 120 reviews

The image captures a serene view of a clear pool reflecting the colorful sunset, framed by a meticulously paved patio. Two cabana beds are positioned next to the pool, with surrounding greenery and a decorative fence enhancing the outdoor space.

Apartment in Burlington

Charming apartment with breathtaking view!

4.95 out of 5 average rating, 169 reviews

A majestic moose stands partially submerged in the calm waters of a pond, showcasing its prominent antlers. Lush greenery surrounds the area, creating a serene and natural atmosphere.

Cabin in Hubbardston

Triggers Cabin

5 out of 5 average rating, 158 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

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.

Apartment in Otis

Enjoy every season the Berkshires have to offer.

4.89 out of 5 average rating, 447 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.

Apartment in Glastonbury

Quiet 2 bed room apt w/ private entrance.

4.97 out of 5 average rating, 151 reviews

An expansive aerial view reveals a private pool surrounded by lush green grass and trees. A small pond is visible nearby, with vibrant foliage framing the scene. Open fields stretch into the distance, highlighting the rural setting on the property.

Home in Windham

mid century ranch style house on farmland