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Kid-friendly vacation rentals in Holyoke

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Top-rated kid-friendly rentals in Holyoke

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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A charming two-story white house is surrounded by greenery, featuring a welcoming front porch with rocking chairs. The structure showcases large windows and a shingled roof, with a pathway leading to the entrance. The tranquil setting is complemented by the rustic stone bench in front.

Home in Litchfield County

4.8 out of 5 average rating, 10 reviews

Charming home ready for fun and/or relaxation!

Enjoy our peaceful (pet friendly) home, at the end of a dead-end road & just a short walk to the center of Norfolk. Great for friends and/or family visits. Board games & puzzles inside; lawn games & fire pit outside. Front & back decks, including screened-in porch, are perfect for relaxing. Access great cafes, shops & cultural delights in Norfolk. The nearby Ellen Battell Stoeckel Estate hosts Yale's Summer Chamber Music Concert series. It’s a home, not a hotel. But, we think you’ll love it!

Top guest favorite

A bright entryway features a white wall with hooks for hanging items and a woven basket atop a built-in bench. Light enters through a nearby window, illuminating the space. A simple blue area rug adds a touch of color, and a door leads outside.

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

A backyard playset is situated on lush green grass, featuring a swing set with two swings and a slide. A small playhouse with a sloped roof can be seen nearby, surrounded by trees providing a natural and shaded environment.

4.94 out of 5 average rating, 144 reviews

Berkshires hideaway! Hikes & serenity near lake

Welcome to your light-filled home in the Berkshires. With a two-level wraparound deck & open floorplan, you can enjoy your time together, away from the world. Big spaces and cozy spots throughout. Perfect for families (with a swingset!) or getaways with friends. Otis Reservoir, MA's biggest lake, is nearby. Audubon preserve behind the house. Great, private home base for hiking, summer music/dance/theatre, trips to Kripalu or MassMOCA, skiing... or for going nowhere at all. Dogs OK! (note: fee)

A vacation house is nestled among tall trees, showcasing a multi-level design. Large windows reflect natural light, providing a connection to the outdoors. A spacious deck is partially visible, blending harmoniously with the surrounding wooded area.

Chalet in Goshen

4.89 out of 5 average rating, 141 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

A lush green backyard features a picnic table accompanied by a vibrant red umbrella. Nearby, two wooden lounge chairs are arranged for relaxation, and a small inflatable pool is set up on the grass. A fire pit adds an inviting element to the outdoor space.

Home in Pittsfield

4.95 out of 5 average rating, 164 reviews

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Home in Bloomfield

4.96 out of 5 average rating, 118 reviews

Spacious Charming New England Cape

Beautiful, relaxing area across from woods. Enjoy sitting on the covered veranda with your coffee or tea in the morning listening to nature and watch the golfers in the distance. In winter bring your x-country skis or snow shoes - just walk across the street and enjoy the golf course trails! Well trained dogs are welcome on the trails in winter too! Close to Skiing, MGM Casino, tons of golf courses, beaches. Need a few more rooms? Ask about our 3br house next door which may be available.

A cozy living area is highlighted by hardwood floors and large clerestory windows. A wooden entertainment console with a television sits beside a lamp with a soft glow. Decorative shelves display books and art, creating an inviting corner next to a wicker chair.

Cottage in Amherst

4.93 out of 5 average rating, 160 reviews

Beautifully Restored Cottage Studio

Originally built as an artist's studio, our Private Cottage is a fully-restored, light-filled, wonderfully serene space - with plush and thoughtful designer-appointed furnishings, cathedral ceilings, hardwood floors, a renovated en-suite bath, and a complete kitchen. Freshly laundered 450+ thread count Egyptian cotton beddings, linens, and towels are provided on-site as are complimentary amenities. * Fully Private, Quiet & Serene, Family-Friendly * An easy 3-minute drive to town

The living area features a light-colored sofa arranged with throw pillows, accompanied by a cozy armchair and a coffee table. Natural light floods through multiple windows, and a round mirror adds depth to the space. A door leads to the outdoor area, enhancing the room's connection to nature.

Home in Litchfield

4.98 out of 5 average rating, 232 reviews

Storybook Cape...HOST & Co.

Step back in time in this classic 1930s Cape Cod home, nestled in the serene beauty of the Litchfield Hills. Just a five-minute drive from the charming Litchfield Green, you’ll find antique shops, cozy cafés, unique boutiques, and a picturesque town center perfect for unwinding. Outdoor lovers will appreciate the proximity to the trails and wildlife of White Memorial Foundation, the peaceful beauty of Topsmead State Forest, and winter adventures at Mohawk Mt. Ski Area.

Top guest favorite

The living area features sloped ceilings with dormer windows, allowing natural light to fill the space. A comfortable seating area includes two gray sofas and a small dining table. A smart TV is mounted on the wall, and a kitchenette is visible in the background.

Apartment in Northampton

4.98 out of 5 average rating, 703 reviews

Tree Top Suite, cozy downtown apartment

This is an entire apartment, close to downtown. It is on the third floor, so you will have to walk up two flights of stairs. Because there are dormers (peaked areas in the ceiling), especially tall people might feel a little cramped in this space. There is a king size bed in the bedroom, a living area that includes a kitchenette, dining area, seating area and a smart TV with a fire stick, and a large bathroom. Outdoor seating on the front porch is for your use only.

Top guest favorite

A spacious living area features a comfortable sectional sofa and two armchairs arranged around a coffee table on a decorative area rug. Natural light enters through multiple windows, and a modern fireplace with a mantel is visible, providing a cozy focal point.

Home in Winsted

4.99 out of 5 average rating, 110 reviews

Cheerful 2 Bedroom Home at Highland Lake

Welcome to the Uncorked Cottage, a fun and relaxing space for you and your family to retreat to. Comfort meets style in this updated home with a cozy remote gas fireplace, 55” smart TV and high speed WiFi. The kitchen is fully equipped cook up your favorite recipes. Located across the street from Highland lake and walking distance to Resha Beach. Just minutes from downtown where you’ll find restaurants and activities for all. Just a short drive to ski mountains.

The front of the house is framed by lush greenery and a vibrant red maple tree. A welcoming red staircase leads to the entrance, while large windows allow natural light to illuminate the interior. The roof is partially covered with clouds, enhancing the outdoor serenity.

4.92 out of 5 average rating, 153 reviews

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Top guest favorite

A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.

4.99 out of 5 average rating, 109 reviews

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

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Popular amenities for Holyoke kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

The modern kitchen features a black countertop with a coffee maker, complemented by a colorful array of mugs on shelves above. A dining area with a wooden table and chairs is visible, illuminated by natural light from nearby windows.

4.96 out of 5 average rating, 45 reviews

Lenox Farmhouse, three blocks to village!

Home in Manchester

4.91 out of 5 average rating, 44 reviews

4BR House- Central Location

Top guest favorite

The kitchen features modern appliances, including an oven and refrigerator, set against stylish gray cabinetry. A patterned area rug lies on the floor, and a window provides natural light. The countertops offer ample workspace, complemented by a decorative backsplash of hexagonal tiles.

Home in West Hartford

5 out of 5 average rating, 13 reviews

Modern Cozy Home for Families & Pets

A spacious kids' bedroom features two sets of bunk beds styled as a castle and pirate theme. A colorful play area with a soft rug showcases a variety of toys. Walls are adorned with whimsical artwork, contributing to a fun and imaginative atmosphere.

Home in Brimfield

4.88 out of 5 average rating, 178 reviews

Little House Inn - Brimmy - Private Home

A rustic red wooden cabin is set against a backdrop of lush green trees. The structure features a sloped roof and a welcoming front porch with steps leading up to it. The surrounding area includes gravel pathways and picnic tables for outdoor gatherings.

Home in Colebrook

4.96 out of 5 average rating, 74 reviews

Log Cabin sleeps 30 bunk style on 350 acres

A wooden deck offers high-top chairs facing a tranquil lake surrounded by trees. The scene includes a spacious grassy area leading to the water, with a gazebo visible in the distance. A gentle mist adds a serene quality to the landscape.

4.83 out of 5 average rating, 144 reviews

Antique Home w Private Pond, Sturbridge /Brimfield

A family game room is featured, showcasing a basketball arcade game and a foosball table. Natural light floods the space from nearby windows, illuminating the wooden flooring and exposed beams. Open areas encourage playfulness, with chairs positioned for seating.

Home in Tolland

4.95 out of 5 average rating, 56 reviews

Spacious Home w/ Hot Tub in Private Lake Community

A bright sunroom features white paneling and large windows that invite natural light. A comfortable couch and a small lamp provide seating, while a sleek desk and white chairs create a workspace. A natural area rug complements the room's decor, enhancing the connection to the outdoors.

4.97 out of 5 average rating, 99 reviews

Stylish Mid-century Modern Berkshires Cape

Kid-friendly apartment rentals

The living area features a plush sofa adorned with decorative pillows, accompanied by a vintage armchair and a small wooden side table. A soft area rug covers the floor, while natural light filters through the window, which has blinds for privacy.

Apartment in Lenox Dale

4.91 out of 5 average rating, 129 reviews

Charming 2BD apartment.

Top guest favorite

A cozy living space features a yellow loveseat adorned with patterned pillows, positioned next to a glass coffee table. Natural light filters through sheer curtains, illuminating the wooden floor and a decorative area rug. A small side table stands nearby.

Apartment in Northampton

4.97 out of 5 average rating, 346 reviews

Light filled three bedroom apartment DT Florence!

The open kitchen and living area features wooden cabinets and sleek appliances. Cozy yellow chairs and a coffee table are arranged in the seating area. A wall-mounted TV is visible, alongside a dining table with black chairs beneath large windows that allow natural light to fill the space.

Apartment in Shelburne Falls

4.87 out of 5 average rating, 430 reviews

Big, sunny 1893 flat steps from Bridge of Flowers

A recreational area within the basement features a wooden foosball table and a seating arrangement comprising a black chair set and an ottoman. A plush leather sofa provides comfortable seating. Bright windows are positioned at the top of the walls, enhancing the space's natural light.

Apartment in Burlington

4.85 out of 5 average rating, 108 reviews

Charming apartment with breathtaking view!

A living room area features two couches, a coffee table, and a flatscreen TV positioned near a decorative fireplace. A shelf above the kitchen area is stocked with dishes and cooking essentials. Warm lighting and soft colors create a cozy environment.

Apartment in Amherst

4.92 out of 5 average rating, 247 reviews

Woodsy hideaway apartment

A comfortable living area is presented with a sofa and two armchairs, arranged around a wooden coffee table. Natural light enters through multiple windows, illuminating the light-colored walls. A ceiling fan offers a refreshing breeze, while an area rug adds warmth to the space.

Apartment in Northampton

4.85 out of 5 average rating, 547 reviews

Parkside downtown cozy apartment

A spacious living area features wooden flooring and a mix of seating options, including a dining table and comfortable chairs. Light streams through large windows, highlighting the high ceiling with exposed beams. Decorative elements like area rugs and wall art contribute to the inviting ambiance.

Apartment in Northampton

4.85 out of 5 average rating, 748 reviews

Down town Florence Temperance Hall

A spacious living area features a large L-shaped sectional sofa adorned with a cozy blanket. A wooden coffee table sits in front on a patterned area rug. Two windows allow natural light to fill the room, and a decorative mirror is mounted on the wall.

Apartment in West Hartford

4.85 out of 5 average rating, 113 reviews

West Hartford Center Apartment

Kid-friendly condo rentals

The living room features a spacious, light-colored sectional couch accompanied by decorative cushions and a comfortable throw. A glass coffee table sits centrally, while wall sconces provide soft lighting. Large windows dressed with sheer curtains allow natural light to fill the space.

Condo in Hartford

4.76 out of 5 average rating, 21 reviews

Lovely two bedroom townhouse with parking

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

Condo in Hancock

4.95 out of 5 average rating, 57 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

An aerial view showcases the resort nestled in the lush greenery of the Berkshires, surrounded by rolling hills. The building features a mix of natural tones, with ample parking visible in the foreground. Ski slopes are seen in the background, emphasizing the mountainside location.

Condo in New Ashford

5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Top guest favorite

A spacious living area is highlighted by two large windows allowing natural light to fill the room. A dark leather sofa is paired with a wooden coffee table and a patterned area rug. A dining table made of wood is positioned nearby, alongside a console table with decorative items.

Condo in Downtown Hartford

4.99 out of 5 average rating, 117 reviews

Posh Pad in The Business District

A cozy living area features a grey sofa, complemented by a vibrant orange armchair. Colorful artwork adorns the wall above, enhanced by two stylish lamps casting warm light. A sleek coffee table sits between the seating, inviting relaxation and conversation.

Condo in New Britain

4.82 out of 5 average rating, 121 reviews

New Britain "Joy of Small Space" Condo

A view of a downtown street, featuring a sidewalk lined with chairs and tables outside a café. Red accents can be seen on the café's exterior. Buildings of varying heights line the street, with greenery visible in the background under a cloudy sky.

4.74 out of 5 average rating, 39 reviews

Downtown Adams Vintage Getaway

A clean and inviting bedroom features a spacious bed with neutral bedding, accent pillows, and soft bedside lighting. Built-in shelves are displayed with decorative items, and a window allows natural light to brighten the area, complemented by light curtains.

Condo in Farmington

4.81 out of 5 average rating, 53 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

Top guest favorite

The exterior of the residence features a two-story wooden structure with stairs leading to an upper-level entry. Natural stone accents and a landscaped area with gravel and trees contribute to the overall aesthetic. Nearby outdoor seating is partially visible in the background.

Condo in Northampton

4.97 out of 5 average rating, 59 reviews

Lovely 1bedrom apartment with screened in porch

Quick stats about vacation rentals that are kid-friendly in Holyoke

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

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