Family-friendly vacation rentals in Chicopee

4.99 out of 5 average rating, 234 reviews

A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.

Cottage in Petersham

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

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.

5 out of 5 average rating, 404 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Guest suite in Belchertown

A spacious house is surrounded by a winter landscape, with snow covering the ground and the roof. A horse grazes near a wooden fence. The chimney rises from the side of the house, framed by tall trees under a clear blue sky.

4.98 out of 5 average rating, 162 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.

Guest suite in South Hadley

A decorative sign featuring an anchor design and the text 'Luke & Ali Riverfront' is displayed prominently. The sign is octagonal and metallic, contrasting with the lush green landscape in the background.

4.84 out of 5 average rating, 132 reviews

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 4 adults and two children. Bunk bed top for children or pull out of 4 adults. 1 bathroom Kayaking Paddle bikes and boards Fire pit Tour boat next door at Brunelle’s Patio Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails l

4.97 out of 5 average rating, 662 reviews

A vibrant red and orange tree stands beside a deep red building, showcasing the beauty of autumn foliage. The tree's colorful leaves contrast with the clear blue sky, while a parked car is visible in the foreground, adding to the peaceful residential atmosphere.

Barn in Northampton

Brookside Carriage House. Private, Great Location.

1890's Carriage House. Bright 850 sq. ft., 2nd flr. studio. Original wood flrs, 12' ceiling, skylights, modern amenities w/ rustic charm. Onsite parking. Two sleeping nooks: One QUEEN, One FULL bed & a leather couch; open floor plan. Shower, laundry, full kitchen, dining table, lounging area, Juliet balconey. Eclectic, spacious, private, quiet, all in a fantastic location. This is a large studio. Staircase to 2nd floor. No TV. Dog friendly; contact me first. Non-Smoking/vaping.

4.93 out of 5 average rating, 189 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!

4.97 out of 5 average rating, 346 reviews

A two-story brick house features a spacious covered porch adorned with planters and an American flag. The entrance is framed by two white doors and decorative accents. Lush greenery and small statues are placed along the walkway, enhancing the welcoming façade.

Home in Holyoke

Explore Holyoke from this charming 3 Bedroom house

This house is settled in a quiet residential neighborhood.Guests have access to the entire second floor,one flight of stairs and you're in.There are lots of windows that brighten the space,with a large dining room,office desk, and a newly renovated bathroom.The living room leads to a beautiful spacious porch over looking the park/playground.All bedrooms have comfortable matresses,lots of pillows, soft sheets,thick super soft towels. Smart TV (Netflix/hulu/sling/roku)

4.99 out of 5 average rating, 140 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, 1,021 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.

4.96 out of 5 average rating, 118 reviews

The living room features a spacious sectional couch adorned with decorative pillows, complemented by a coffee table at its center. A cozy armchair with a contrasting cushion sits nearby. Natural light streams through two large windows, enhancing the warmth of the space.

Apartment in Chicopee

Cozy Brick House in Chicopee

Relax with the whole family at this peaceful place to stay. The unit is part of a two family duplex house. You and your family will have the entire unit to yourselves. There are two bedrooms with queen size beds, a living room, kitchen, bathroom, and laundry room. The living room has a TV, fireplace, and Netflix. There is also a fenced in back yard with a patio and outdoor dining area as well as a firepit. The house is also pet-friendly.

4.81 out of 5 average rating, 279 reviews

A clear, inviting pool is surrounded by lush greenery and mature trees, providing a serene and private atmosphere. The pool features a gently curving shape and is bordered by textured stone paving, with sunlight reflecting off the water's surface.

Apartment in Holyoke

NE Historical Mansion-pets and pet lovers welcome

Enjoy seamless check-in and a private 1,000 sq ft space on the third floor of our historic Victorian home. Includes 2 bedrooms, bathroom, open hallway, and a combined living/dining/kitchenette area (no sink). Pet-friendly, updated, and comfortable year-round. Accessed via the back staircase; only the entry/hallway is shared. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

Guest suite in South Hadley

The exterior view showcases a charming farmhouse with yellow siding and white trim. A set of stairs leads up to the front door, framed by a covered porch supported by decorative columns. Green grass surrounds the entrance, providing a tranquil setting.

4.94 out of 5 average rating, 327 reviews

Charming 3BR | Private 2nd-Fl Escape Near MHC

Enjoy privacy and charm in this renovated 3-bedroom, 1-bath second-floor suite of our 1875 farmhouse! This peaceful retreat offers a private entrance, modern amenities, and easy self check-in. Walk to Mount Holyoke College and Village Commons, or take a short drive (less than 20 minutes) to Amherst and Northampton. Perfect for families, couples, or university visitors seeking a quiet, historic home away from home.

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, 225 reviews

Guest suite in Mansfield

Cozy private apt 8 mins from UCONN - solar powered

4.91 out of 5 average rating, 112 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.

Home in Columbia

Breathtaking home with unforgettable views & pool!

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, 115 reviews

Sweet suite, walk to town tout suite!

4.93 out of 5 average rating, 550 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

Guest suite in Springfield

A stylish bedroom is presented with a dark upholstered headboard and an array of decorative pillows on the bed. Two light-colored armchairs with patterned cushions are positioned in front of the bed. A chandelier and wall art enhance the elegant design, while soft blue walls create a soothing backdrop.

4.89 out of 5 average rating, 192 reviews

The Cobalt Blue Room at Smith Manor

4.96 out of 5 average rating, 139 reviews

A spacious porch is presented with a sectional outdoor sofa and a glass coffee table. Potted plants add a touch of color. Scenic views of green fields and distant mountains are visible, under a bright sky adorned with fluffy clouds.

Guest suite in Hadley

Hadley Hay House | No Cleaning fees!

4.85 out of 5 average rating, 343 reviews

An outdoor deck features a hot tub, providing a relaxing space. Comfortable seating is arranged with turquoise cushions around a central fire pit. A gas grill is positioned nearby, and a shade sail provides coverage from sunlight. The surrounding neighborhood is also visible.

Townhouse in Easthampton

In style row house with private hot tub/pool table

4.99 out of 5 average rating, 143 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

Peaceful Snowy Lake Views from Private Hot Tub

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 230 reviews

A classic log cabin stands surrounded by greenery, featuring a spacious front porch with a wooden railing. Large windows dominate the front, allowing natural light to fill the interior. An American flag is displayed, adding to the rustic charm of the structure.

Cabin in Plainfield

Peaceful Cabin in the Woods

4.95 out of 5 average rating, 304 reviews

Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

4.89 out of 5 average rating, 419 reviews

The cozy cottage is nestled among trees, featuring a welcoming wooden deck. Reflections of the structure can be seen in the calm water of the pond, surrounded by lush greenery. A kayak is positioned in the foreground, pointing towards the entrance.

Tiny home in Orange

The Writer's Retreat: A Sweetwater Stay

4.95 out of 5 average rating, 115 reviews

A rustic cabin is visible in a snowy landscape, surrounded by tall trees and a wooden fence. The cabin is partially obscured by falling snowflakes, creating a serene and tranquil winter scene. Soft snow covers the ground and branches, enhancing the winter atmosphere.

Cabin in Colebrook

Rustic Pond Cabin: Nature, Stars & Serenity

Apartment in Williamsburg

The spacious studio apartment features a well-equipped kitchen with a countertop and bar seating. Natural light filters through the windows, highlighting wooden cabinetry and modern appliances. The open layout includes a cozy seating area, creating a functional living space beneath sloped ceilings.

4.96 out of 5 average rating, 143 reviews

The cozy clubhouse

4.87 out of 5 average rating, 239 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

4.98 out of 5 average rating, 112 reviews

A charming garden area is enclosed by a white picket fence, featuring an array of colorful flowers and tall sunflowers. The gray facade of the house provides a serene backdrop to the vibrant foliage, creating a welcoming atmosphere in the outdoor space.

Apartment in Conway

House Above the Hollow

4.92 out of 5 average rating, 300 reviews

A chalet-style home is situated on a forested property, with a spacious deck extending from the front. Large windows reflect the surrounding greenery, showcasing a modern aesthetic against a backdrop of autumn foliage. Rock formations and scattered leaves cover the ground.

Chalet in Peru

Swiss Chalet Style Timberframe Home in Berkshires

Family-friendly home rentals with a 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!

5 out of 5 average rating, 168 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

Guesthouse in Glastonbury

A well-maintained grass area leads to a fenced saltwater pool, surrounded by colorful trees displaying autumn foliage. The pool house features a charming design, positioned adjacent to the pool, while a stone pathway guides visitors through the scenic landscape.

4.77 out of 5 average rating, 100 reviews

59 Old Maids Lane pool house

4.96 out of 5 average rating, 121 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.

4.93 out of 5 average rating, 202 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

4.97 out of 5 average rating, 153 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

4.97 out of 5 average rating, 134 reviews

A large farmhouse is depicted in the background, featuring a broad balcony and distinctive architectural details. Sunflowers are prominently featured in the foreground, with bright yellow petals and green leaves, surrounded by lush grass and trees providing a serene atmosphere.

Barn in Bloomfield

Mountaintop Horse Farm with Pool