Family-friendly holiday rentals in Wareham

5.0 out of 5 average rating, 251 reviews

The cottage exterior is illuminated by warm lights, showcasing a spacious deck with inviting seating. Lush greenery surrounds the property, with a vibrant purple flowering bush nearby. The serene atmosphere is enhanced by the evening sky, providing a cozy and welcoming retreat.

Cottage in Marion

Little Boho Retreat by the Beach

Kick back and relax in the most calming, low charm country, coastal cottage the town of Marion has to offer. You’ll experience spectacular view of the beach right from the deck to watching the boats from the harbor. Don’t just limit yourself to life at the beach in just the summer months, come and make memories in this beautiful year-round cozy cottage. It's a perfect retreat to go swimming, kayaking, fishing, bird/seal/crabs watching and more right here in a private community on Dexter Beach.

4.92 out of 5 average rating, 219 reviews

An aerial view highlights the scenic Onset area, showcasing the nearby beach and water bodies. The renovated Sea Captain's house is marked, surrounded by a largely residential neighborhood with streets leading to the coastline.

Apartment in Wareham

☀️ Spacious and Bright -- The Sailboat Suite

Spacious, open, and bright, the Sailboat Suite is in an amazing location just steps from Onset Beach, village, boat rentals, market, & restaurants! Located on the first floor of a renovated Sea Captain's house, this large apartment gets great natural light. A/C included in all bedrooms. Fully stocked kitchen. Fiber WiFi & Smart TV. Nice covered deck with park and bay views. One of the very best locations in Onset! Pet friendly as well 🙂 Perfect spot for a beach getaway or family vacation.

5.0 out of 5 average rating, 249 reviews

A historic home features classic New England architecture, with a peaked roof and wooden shingle siding. White trim outlines the windows and door, while a white picket fence surrounds the property. Lush greenery and colorful flowers enhance the welcoming exterior under a clear blue sky.

Home in Sandwich

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

4.83 out of 5 average rating, 256 reviews

The exterior of the cottage is shown, featuring a welcoming blue door and a well-maintained front yard with colorful flowers. The view includes a quiet street lined with trees and nearby houses, providing a glimpse of the neighborhood atmosphere.

Cottage in Fairhaven

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

4.93 out of 5 average rating, 86 reviews

The Perfect Restful Retreat

Escape to our newly renovated two-bedroom home peacefully nestled between the serene ponds in beautiful East Wareham. Our home offers the perfect blend of modern comfort and New England tranquility. Whether you're seeking a relaxing retreat or an adventurous getaway, our charming modern home is the perfect base being centrally located to all the attractions and activities that make Wareham, the gateway to the Cape, so special. Book your stay today and create unforgettable memories!

4.85 out of 5 average rating, 286 reviews

A serene view of a clear, spring-fed pond is visible, edged by lush greenery. A wooden dock extends into the water, inviting activities such as swimming or kayaking. Gentle waves ripple on the surface, reflecting the surrounding trees under a clear blue sky.

Cottage in Wareham

Cozy Cottage on a Private Pond

This cozy cottage is located on a private 42 acre, spring fed, crystal clear private pond. Enjoy kayaking, swimming or fishing from the dock or just relax on the deck overlooking the pond. Sleeps 5 in 2 bedrooms and trundle bed in the 4 season room. There is good fishing and canal cruises, cafes and restaurants close by and a summer concert series in park. Many of our guests with children have visited Edaville Railroad and "Thomasville" It is about 15 miles from the cottage

4.89 out of 5 average rating, 101 reviews

A lagoon-style pool surrounded by a concrete deck provides lounge chairs and shaded areas under umbrellas. A gazebo is visible in the background, complementing the lush greenery that borders the property.

Villa in Wareham

Perfect Farmhouse Discounted for Draft Day!

Old Red Farm Inn invites you to forget your worries in this charming space that has everything to offer. Originally built in 1700’s, this updated Inn can be your sanctuary! A perfect fall getaway! A lagoon pool on site, a golf course across the street, walking distance to Little Harbor Beach, and acres of conservation land for hiking provides everything you need in order to relax. This home is over 5,000 ft. and can fit multiple families that are looking for a fun getaway.

4.97 out of 5 average rating, 246 reviews

A handcrafted tree house is perched among trees, supported by wooden stilts. The structure features a rustic exterior with a metal roof and large windows, surrounded by greenery and vibrant pink flowers in the foreground, creating a serene and natural setting.

Treehouse in Wareham

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

4.96 out of 5 average rating, 246 reviews

The kitchen features stainless steel appliances, including a refrigerator and a gas stove. Light grey walls are complemented by granite countertops. Natural light enters through a window above the sink, with kitchen essentials and decor items visible on the counters.

Townhouse in Wareham

The Gateway to Cape Cod townhouse !

Summer of 2027 calendar open BEACH PASS PROVIDED PLEASE CHECK OUT SLEEPING ARRANGEMENTS PRIOR TO BOOKING MAX 6 adults only Ideal for families Parking for 2 vehicles only WELCOME to Wareham! The town with the most coastline out of any town in MA 60 miles! Minutes to Water wizz and TONS of local beaches! Wareham center and a local grocery store are both walking distance away! Great proximity to Boston , providence , Plymouth, Cape and Bourne

A serene sunset over a calm body of water reflects vibrant orange and soft blue hues. Lush green grass borders the shore, while silhouettes of distant trees frame the scene. A dock is visible on the left, offering a peaceful spot to enjoy the view.

4.99 out of 5 average rating, 120 reviews

Sunset Cove Beach

This ocean view cottage is perfect for you and your family to relax, unwind and adore the wonderful scenery it has to offer. This charming cottage is on a quiet dead-end street, suitable for a small family or a couple, seeking to appreciate the neighborhood and beaches without the hassle of cape traffic. Come and enjoy the warm water, beautiful sunrises, breathtaking sunsets, and much more.

The exterior of the cottage is presented, showcasing a light-colored façade with dark shutters. Steps lead to the inviting entrance, framed by a decorative awning. Lush greenery and well-maintained flower beds enhance the front yard, contributing to a welcoming atmosphere.

4.95 out of 5 average rating, 105 reviews

The Flirty Flamingo-Wareham, Ma

Welcome to The Flirty Flamingo, a stylish coastal retreat near Cape Cod’s beautiful beaches. This bright, family-friendly home blends seaside charm with modern comfort, featuring a fully equipped kitchen, air conditioning, and inviting spaces to relax after a day of exploring. Conveniently located near Boston, Cape Cod, and Gillette Stadium, it’s the perfect home base for your getaway.

A wooden basket filled with neatly rolled towels is placed on a table. An outdoor deck is visible with white chairs, surrounded by greenery. A dining table is set with dishes and utensils, while a scenic view of a salt marsh and blue skies is showcased in the background.

4.89 out of 5 average rating, 284 reviews

The Light House - on the water, secluded, kayaks

On the water on private quiet cul de sac with breathtaking views & two decks. Just 3/10 of a mile walk to 2 beaches & Onset village with great restaurants & attractions. Kayak right from our backyard. Kayaks provided! Hot/cold outside shower. Outdoor deck dining. Dishwasher, Washer, dryer, WIFI. Window AC units in all bedrooms. Onset, the gateway to Cape Cod.

Popular amenities for Wareham family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 320 reviews

The cottage, surrounded by mature landscaping, is located near a private beach. A sandy expanse is visible in the background, highlighting the close proximity to the shore. Nearby structures exhibit a rustic charm, contributing to the serene beach environment.

Cottage in Sandwich

Hideout at Water's Edge, 131 North Shore Blvd, #4

4.97 out of 5 average rating, 127 reviews

A covered outdoor seating area features a comfortable sectional sofa with neutral cushions and a round coffee table. A dining table with several chairs is positioned nearby, alongside an outdoor kitchen equipped with a grill. Sunlight casts distinct shadows across the space.

Home in East Falmouth

Seacoast Shores Oasis-Steps From Private Beach Bay

4.95 out of 5 average rating, 126 reviews

An open living area is highlighted by vaulted ceilings and large windows that allow natural light to illuminate the space. A comfortable seating arrangement faces a coffee table, while a dining area with bar stools is situated near the kitchen. A spiral staircase leads to the upper level.

Guest suite in Plymouth

Manomet Boathouse Station #31

4.99 out of 5 average rating, 197 reviews

A spacious wrap-around porch is shown with comfortable seating, offering panoramic views of the waterfront. The warm glow of sunrise reflects on the water, and a distant bridge is visible under a clear sky. The setting invites relaxation and enjoyment of the serene environment.

Home in Somerset

Beachfront W/ HotTub, Sauna, Pool & Panoramic view

4.88 out of 5 average rating, 129 reviews

Home in Somerset

Fall and Holidays, Entire Home w/ Jacuzzi PETS

4.98 out of 5 average rating, 172 reviews

The exterior of the house is surrounded by well-maintained greenery and tall, lush trees. A welcoming front entrance is framed by neatly trimmed hedges, leading to a slate pathway and steps. Large windows allow natural light to brighten the façade.

Home in Centerville

Luxury House 0.25 mi from Craigville Beach

4.98 out of 5 average rating, 178 reviews

An outdoor dining area overlooks the tranquil cove. The table is surrounded by six wicker chairs, set against a backdrop of calm blue water and a clear sky dotted with fluffy white clouds.

Cottage in Portsmouth

Waterfront Oasis minutes from Newport w/ hot tub!

4.94 out of 5 average rating, 125 reviews

Guesthouse in Sandwich

Nautical loft guest house with hot tub and sauna

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 355 reviews

A cozy living space features a striped sofa and a round table set near a rug. Light from the windows brightens the room, which leads to a bedroom visible in the background, adorned with a patterned quilt and vibrant pillows.

Cottage in Pocasset

Upper Cape Cozy Cottage

5.0 out of 5 average rating, 172 reviews

A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.

Home in Falmouth

Private Pond-side Cape Cod Home

4.97 out of 5 average rating, 222 reviews

An open-concept living space showcases a well-equipped kitchen featuring a retro blue refrigerator and modern appliances. A comfortable sofa with decorative pillows faces the kitchen, with a wooden dining table positioned nearby. Light streams in through a nearby window, complementing the warm tones of the decor.

Apartment in Bourne

A Shore Thing (King Bed, private patio w/ grill)

4.93 out of 5 average rating, 131 reviews

The exterior of the cottage features a raised deck with a lattice design, offering a clear view of the entrance. Brightly colored umbrellas and planters add subtle touches to the space. A gravel pathway leads to the stairs, surrounded by greenery.

Cottage in Buzzards Bay

Buzzards Bay - Beach Bungalow

4.81 out of 5 average rating, 130 reviews

The charming beach cottage features a light-colored exterior with multiple windows, framed by lush greenery and well-maintained bushes. A grassy lawn leads to the entrance, with a clear path visible and surrounding trees providing a natural backdrop.

Cottage in Bourne

Adorable Gray Gables Beach Cottage

4.85 out of 5 average rating, 470 reviews

An outdoor seating area is presented with a fire table at its center, illuminated by flames. Comfortable chairs surround the fire, with a red umbrella providing shade above. The ocean and sunset create a serene backdrop, showcasing vibrant colors across the sky.

Cottage in Sandwich

Bold Oceanfront Cottage w/Pvt Beach ~ Lil Sea Sass

4.92 out of 5 average rating, 106 reviews

An open floor plan living area features a light-colored sofa adorned with teal accent pillows, complemented by a plush gray rug. Large windows provide a view of the ocean, while a dining area is visible in the background, surrounded by wooden beams and natural light.

Home in Buzzards Bay

Relax by the Sea, Cozy 2 bedroom home

4.97 out of 5 average rating, 167 reviews

The exterior of a charming multi-level home is showcased, featuring a spacious deck with seating and an umbrella. A stairway provides access to the upper level, surrounded by lush greenery. Large windows offer views of the wooded surroundings, creating a sense of integration with nature.

Home in Falmouth

Mid-Century Modern home 5 minute walk to beach

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 103 reviews

Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

4.9 out of 5 average rating, 199 reviews

A serene pool area is surrounded by lush gardens, featuring vibrant flowers in planters. A pool house is visible in the background, framed by greenery. The clear water of the pool reflects the surrounding natural beauty, inviting relaxation and enjoyment.

Home in Plymouth

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

4.97 out of 5 average rating, 183 reviews

Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

4.94 out of 5 average rating, 110 reviews

A cozy studio space features sloped ceilings and warm wooden flooring. A spacious bed is dressed in white linens, with accent pillows adding a touch of color. A small kitchenette is visible beside a comfortable chair and a blue rug, offering a relaxed atmosphere.

Guest suite in Dartmouth

The Loft @ Beechwood. Private, comfy, coastal!

Guest suite in Centerville

“The Hideaway”Private Guest Suite/Pool/Beach Pass

4.99 out of 5 average rating, 105 reviews

4.96 out of 5 average rating, 146 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

4.97 out of 5 average rating, 264 reviews

A scenic view showcasing the bay with gently rippling waters and distant land on the horizon. The foreground features coastal vegetation, including pines and shrubs, along a wooden pathway leading toward the beach. Nearby, a stop sign indicates road access.

Condo in Provincetown

P-Town Beach Beauty on the Bay. Water View!