Family-friendly holiday rentals in Wareham

5 out of 5 average rating, 232 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, 186 reviews

Home in Plymouth

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

4.92 out of 5 average rating, 207 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.

Flat 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.

A tranquil waterfront scene is illuminated by twilight, showcasing a calm body of water reflecting the deep blue and orange hues of the sky. A small boat rests gently near the shore, surrounded by grasses, while trees outline the distant horizon.

5 out of 5 average rating, 11 reviews

Waterfront, 10 minutes to Cape Cod & Mass Maritime

Relax with family and friends at this waterfront glass-front beach cottage—your new favorite hideaway. Enjoy 2 bedrooms with new Sealy queen beds, a queen Lazy Boy sleeper sofa in the living room, vaulted ceilings, a full kitchen with coffee bar, and a washer and dryer. Take in views of Crab Cove with 2 kayaks and a canoe, or unwind under the power awning and a comfortable table for 6. Includes fire table, Adirondack chairs, and more. Just 8 miles from Cape Cod—your perfect getaway awaits!

Tiny home in Mattapoisett

A welcoming living area features comfortable electric recliners and a small table, set against neutral-colored walls. A nautical-themed rug lies on the floor, while wall art and colorful flags add character. Natural light flows in through the window, which is adorned with blinds.

4.99 out of 5 average rating, 139 reviews

101 Steps to Beach/Island/Bike Path

Experience the Seaside Town of Mattapoisett. Location! Relax in this cozy cottage that is 101 steps from the front door to the Beach/Island/Bike Path. Enjoy this popular, sought after scenic Path for walking, biking, or a day at the Beach. The path is known for its picturesque coastal views. Walking distance to the Quaint Town, Shipyard Park, and many great restaurants. Ned's Point Lighthouse- 5min. Day trip to the Vineyard? Ferry- 14 min. 10% off Sept/Oct. 10% off 4 or more nights.

The exterior of the beach house features a gray shingle facade, with a large front door framed by multiple windows. Flowers are planted along the stone walkway, while two white Adirondack chairs are positioned on the well-maintained lawn, providing views of the water nearby.

4.98 out of 5 average rating, 64 reviews

Peaceful waterfront home, large deck, 4 bedrooms

Nestled in Broad Cove on Buzzards Bay, this inviting home is perfect for family gatherings. The open-concept first floor connects the kitchen to the living room, offering stunning bay views through 3 sliding glass doors. Upstairs, find 4 bedrooms, including a master suite overlooking the water. Enjoy 65 feet of private beach and easy access to Onset beach and restaurants, just a 15-20 minute walk or 5-minute drive. A coastal retreat that blends convenience with scenic tranquility.

4.81 out of 5 average rating, 141 reviews

Cottage in Wareham

Charming cottage just 100 steps from the beach!

This beach cottage just steps from beautiful Onset Beach was restored in 2021. It boasts a brand new bathroom and kitchen, new flooring throughout and is tastefully decorated in coastal blue hues with a touch of shabby chic. Walk to the beach without having to pay or battle parking. You are also a 3-5 minute walk to restaurants, the grocery store, an ice cream parlor and more. Hot/cold outside shower. Window AC units in bedrooms & living space. Onset, the gateway to Cape Cod.

4.84 out of 5 average rating, 281 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

Superhost

5 out of 5 average rating, 3 reviews

Fun and Sun on the Bay! Waterfront- Slps 6!

Wake up to sparkling bay views and spend your days steps from the water at this beautifully renovated waterfront retreat in the heart of Onset. With direct access to Broad Cove, a spacious waterfront patio, stunning views from the living room, and a bright coastal interior, Sun and Fun on the Bay is the perfect place to relax, reconnect, and create lasting memories. Enjoy beach days, waterfront dining, and peaceful evenings by the fire—all from one unforgettable location.

4.93 out of 5 average rating, 190 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!

Avail Summer 26’ July 12-16 20-23 Aug 23-28 Sept 9-11,21-30 BEACH PASS PROVIDED Please read Can sleep a 6th SMALL CHILD (5 or under) in this unit. 5 adults MAX parking for 2 cars only FAMILY FRIENDLY WELCOME to Wareham,the town with the most COASTLINE out of any town in Mass (60 miles!) Minutes away from Water wizz and TONS of local beaches.Wareham Center and a local grocery store are both walking distance away! Near Plymouth, Cape, Boston and providence

4.97 out of 5 average rating, 231 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.

An indoor game wall is featured, showcasing a variety of games displayed on wooden panels. A small, cozy table with a dark finish sits nearby, creating a casual gathering space for guests to enjoy games or meals together.