Family-friendly holiday rentals in Wareham

4.94 out of 5 average rating, 171 reviews

The kitchen area features modern stainless steel appliances, including a gas range and a dishwasher. A granite countertop is prominently displayed, alongside an assortment of cooking oils and spices on the shelves above. A kettle rests on the stovetop, adding functionality.

Loft in Wareham

The Gateway to Cape Cod Loft!

SUMMER 2026 is OPEN BOOK QUICK November 12-21 open at a great rate BEACH PASS PROVIDED PLEASE READ PERFECT FOR FAMILIES Can sleep a 6th SMALL CHILD (5 or under) in this unit if needed 5 adults MAX parking for 2 cars only WELCOME to Wareham, the town with 60 MILES of shoreline in Massachusetts! Minutes away from Water wizz and TONS of local beaches. Wareham Center and a local grocery store are both walking distance away! Near Plymouth and Cape. Great proximity to Boston and providence.

4.79 out of 5 average rating, 195 reviews

A calm waterway reflects soft pastel colors during sunrise, with silhouettes of boats anchored in the distance. Gentle grasses line the foreground, and the tranquil landscape is framed by hills on the horizon, offering a serene morning view.

Guest suite in Pocasset

Rustic Beach Cottage

The salty air will instantly wash all your cares away. This rustic charming Cape get away is steps away from a quaint quiet picturesque beach. Simply relax in the comfortable surrounds in this fully furnished 1 bedroom Cottage apartment with all of your basic needs including WiFi, Smart TV, A/C, and a deck complete with gas grill and outdoor furniture offering you plenty of living space inside and out. Close to the bike paths, Cape Cod Canal, great restaurants, hiking, ferry and much much more!

4.99 out of 5 average rating, 197 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, 195 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 Onset

☀️ 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.

4.78 out of 5 average rating, 120 reviews

A cozy living area is presented with a dark couch and a wooden dining table accompanied by black chairs. A TV is situated on a light-colored media unit, while bookshelves filled with books line one wall. Natural light filters in through sheer curtains.

Apartment in Fairhaven

Main Street on the Park

Welcome to Main Street on the Park! The morning sun will greet you in the bright apartment in our big white house with a yellow front door. Perfect for a romantic getaway or a convenient place to stay if you are in the area for business. A large fenced yard abuts a public park complete with tennis courts, track and walking trail. Explore our small town with a big history, visit its historic buildings, great restaurants and unique shops. The location is convenient to all of the South Coast.

4.84 out of 5 average rating, 164 reviews

A spacious deck area features a wooden railing overlooking a private lake. The calm water reflects the surrounding greenery, with a dock visible in the distance. Outdoor furniture is arranged nearby, offering a place to relax and enjoy the tranquil setting.

Cottage in Wareham

Onset beach, Cape code.Private Waterfront cottage

PRIVATE LAKE FOR YOUR Vacations year around. Spend quality time on spectaculars Blackmore pond.Comfortable cottage,step away from the water.Your own big dock out of your house as you wake up .Enjoy sunshine and sunset during summer , beautiful foliage , experience the ice or Snow drop during winter. this is exceptional romantic for your family . Well located next Onset beach, Water Park , Water Wizz of Cape Code. , Gate to Cape , To Ferry to Nantucket, Martha vineyard, Plymouth to P-Town

4.98 out of 5 average rating, 315 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

Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.

4.97 out of 5 average rating, 261 reviews

A spacious bedroom features a large king bed with a custom wood frame and soft bedding. Natural light enters through two windows with sheer curtains, and a colorful abstract art piece adorns the wall. A full-length mirror stands adjacent to the bed on a textured area rug.

Apartment in Falmouth

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

4.88 out of 5 average rating, 150 reviews

The exterior of Salt Tide Cottage is shown, featuring a white-sided structure with a dark blue door and a large star decoration. A small seating area with two chairs and a table is positioned in front, surrounded by well-maintained green grass and trees.

Guesthouse in Barnstable

Relaxing Cottage in Centerville Village

Welcome to my home! The cottage is located in Historic Centerville Village, it's a welcoming, bright and relaxing, studio space; perfect for a couple, or individual, to getaway on Cape Cod. Salt Tide Cottage is a private guesthouse with off-street parking and a serene outdoor space. It sits behind the main house with its own back yard space with hammock. Just a short walk to the ocean, beaches, the library and the general store.

Apartment in Mattapoisett

A modern kitchen is showcased, featuring navy blue cabinetry and wooden countertops. Equipped with a stainless steel refrigerator, oven, and a farmhouse sink, the space includes a toaster and coffee maker. Shelves display dishware, while bright light enhances the welcoming atmosphere.

4.98 out of 5 average rating, 133 reviews

Brand new! Whole apartment, huge tub, full kitchen

Beautiful self-contained apartment. Enjoy the blissful extra-long Kohler soaking tub, rain shower, and luxurious Matouk towels. Full kitchen and outdoor seating area. DreamCloud queen bed. Short walk to the center of the village and town wharf, providing easy access to all of Mattapoisett's charm, including Ned's Point Lighthouse and Town Beach. Outstanding local restaurants and sweet treats all close by.

4.96 out of 5 average rating, 306 reviews

A serene view of a tranquil lake is captured, featuring swans gracefully gliding across the water. Lush green grass and trees frame the scene, while a backdrop of softly shaped clouds enhances the peaceful atmosphere. Houses are visible in the distance, harmonizing with nature.

Cottage in Wareham

Cottage on Sunset Cove

Bright sunny cottage on Sunset Cove in East Wareham just minutes from the Bourne Bridge. Enjoy some quiet time watching the swans or drive to one of the many attractions the Cape and surrounding areas has to offer. state of Massachusetts certification code: c0195503100

4.8 out of 5 average rating, 225 reviews

A serene beach scene is captured at sunset, displaying gentle waves lapping at the shore. The sky transitions through warm colors of orange, pink, and soft purple, while the calm water reflects these hues, enhancing the peaceful ambiance of the coastline.

Guesthouse in Plymouth

A peaceful retreat on Cape Cod Bay

Just steps from an association beach, this quiet, one-bedroom, guest cottage hosts a king bed, a little breakfast nook, and a comfortable bathroom. Anyone seeking social distancing will find this the perfect getaway retreat.

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

4.97 out of 5 average rating, 195 reviews

A welcoming entryway is observed, featuring a rustic 'WELCOME' sign on the wall. Light wood flooring extends into a cozy living and dining space, illuminated by natural light. A dining table is visible in the background, surrounded by comfortable chairs.

Condo in Brewster

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

4.92 out of 5 average rating, 287 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 East Sandwich

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

4.96 out of 5 average rating, 136 reviews

Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.

Cottage in South Dennis

Local Beach+ Fireplace + Hot Tub Under the *Stars*

4.94 out of 5 average rating, 102 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

4.93 out of 5 average rating, 209 reviews

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

4.83 out of 5 average rating, 345 reviews

A hot tub emits a soothing green glow, surrounded by softly illuminated string lights. The tranquil outdoor setting features trees in the background and hints of nearby greenery, creating a relaxing atmosphere for evening enjoyment.

Home in Plymouth

Historic 1 Bed/In Town/Best Location/Hot tub/deck

4.9 out of 5 average rating, 306 reviews

A hot tub is situated under a wooden pergola, surrounded by trees reflecting natural greenery. Soft lighting is arranged along the structure, creating a calm ambiance. The tub is partially covered, with jets visible, inviting relaxation after a day at the beach.

Home in West Dennis

Sun Sand & Sea House- Fenced Yard and Hot Tub!

4.94 out of 5 average rating, 116 reviews

An open living area features a large sectional sofa with decorative cushions, complemented by wooden beams and a high ceiling. A modern kitchen with dark cabinetry and stainless-steel appliances is visible in the background. Framed photographs adorn the walls, adding character to the space.

Home in Cranston

Relaxing retreat in the village

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 256 reviews

Cottage in Sagamore

Beach Cottage, without going over bridges to Cape!

4.93 out of 5 average rating, 125 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

4.97 out of 5 average rating, 208 reviews

The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.

Guest suite in Sharon

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

4.94 out of 5 average rating, 308 reviews

A serene view of the Westport River at dusk features soft pastel hues reflecting on the water. A wooden dock extends into the calm river, framed by gentle grasses in the foreground. The sky transitions from deep blue to warm oranges and yellows as the sun sets.

Cabin in Westport

Koselig Cabin on the Farm Coast of New England!

4.81 out of 5 average rating, 118 reviews

A charming two-story cottage is set amidst lush greenery, featuring a light-colored exterior with large windows. An outdoor deck includes a gas grill, while a stone pathway leads to an arched trellis, enhancing the inviting outdoor space.

Home in Orleans

Cute Cottage Living by the Sea!

4.92 out of 5 average rating, 354 reviews

A newly remodeled kitchen features modern stainless steel appliances and ample counter space. White cabinetry contrasts with warm wood paneling and flooring. A dining area with a wooden table and chairs is visible, along with soft lighting from pendant fixtures above.

Cabin in Cohasset

Lionsgate at Cohasset

4.96 out of 5 average rating, 150 reviews

Soft waves gently lap against smooth stones along a sandy beach. The tranquil water reflects the pastel hues of the sky, creating a serene coastal scene. In the distance, small waves ripple towards the horizon.

Cottage in Plymouth

Coastal Cottage — 7 min walk to private beach

5 out of 5 average rating, 105 reviews

Two black Adirondack chairs are positioned around a small table in a serene backyard setting. A bowl filled with lobster sits atop the table, with a fish pond and rocks in the background, complemented by sun rays filtering through the foliage.

Apartment in Sandwich

Cozy Large Private Pet Friendly Studio

Family-friendly home rentals with a pool

5 out of 5 average rating, 45 reviews

An aerial view captures the estate's expansive layout, featuring two charming buildings, a central saltwater pool, and a clay tennis court. Surrounded by greenery, the property showcases landscaped areas and pathways, creating an inviting outdoor space suitable for various activities.

Home in East Sandwich

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl

4.86 out of 5 average rating, 103 reviews

An outdoor area is featured with a swimming pool surrounded by a decorative fence and lush greenery. Patios with seating arrangements and an umbrella provide shaded spots for relaxation. Colorful flower pots add vibrant accents along the poolside.

Home in Barrington

Cozy Barrington Home with a Private Pool

4.94 out of 5 average rating, 105 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!

4.74 out of 5 average rating, 69 reviews

A light-filled living area features comfortable seating with blue and white accents. A natural wood coffee table sits in the center, surrounded by a cozy area rug. A separate dining space is visible through an open archway, showcasing a charming dining table and decorative elements.

Home in Plymouth

Tranquil Home with Pool, Fireplace, and Game Room

Apartment in North Falmouth

A charming stone exterior features a distinctive arched design, with two red doors providing access to the private studio. Lush greenery surrounds the entrance, complemented by a gravel pathway and neatly trimmed bushes, evoking a sense of tranquility in the outdoor space.

4.8 out of 5 average rating, 114 reviews

Falmouth, Cozy Studio Near Old Silver Beach

4.98 out of 5 average rating, 105 reviews

A cozy living area is furnished with a comfortable sofa adorned with decorative pillows. A dining table with seating for four is visible, alongside a well-equipped kitchen in the background. Natural light enters through the windows, highlighting the warm wood floors.

Apartment in Wellfleet

Rock on Wellfleet!

5 out of 5 average rating, 24 reviews

A charming two-story house is featured, with a light gray exterior and blue front door. The inviting porch is furnished with wooden rockers, surrounded by manicured shrubs and vibrant pink flowers. Windows are symmetrically placed, creating a balanced, welcoming appearance.

Home in North Falmouth

New Construction Home with Pool in N. Falmouth