Family-friendly vacation rentals in Plymouth

Cozy Ladybug Cottage Near Cape Cod Canal

My cozy lil'Ladybug Cottage located on a rustic dead end street w/Great Herring Pond at end of road and tennis/basketball courts w/playground across from the other end of the road-make a perfect spot! Centrally located to major roads, highways &convenient to historic Plymouth/Sandwich. Easy to explore and enjoy the Cape Cod canal, ocean beaches as well as recreational activities nearby. Hike trails @ Ellisville Harbor State Park/picnic at the Herring run or canal, or grab a game of golf nearby.

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.

The Gateway to Cape Cod Loft!

SUMMER 2026 is OPEN BOOK QUICK JULY 4th 2026 OPEN! Christmas 2025 open! 24-28th BEACH PASS PROVIDED PLEASE READ GREAT 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, Boston and providence, RI

Manomet Boathouse Station #31

The Boathouse was a part of the Manomet Coast Guard Station on Manomet Point. When the station was decommissioned and eventually dismantled, the Boathouse was moved and attached to our home as a separate space. Guests will have full and private access to this beautiful and spacious 1,800 square foot home with 11 foot vaulted ceilings and antique southern exposure windows. The open first floor has a living room, kitchen, pool table and bathroom. A spiral staircase leads to the bedroom.

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.

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

Tiny farm house on horse farm

Set in a quiet cul-de-sac at the end of our driveway, this tiny house is part of our family compound and working horse farm. We have many animals. Enjoy your space, knowing we are just 50 yards away should you need anything. This is a true tiny house experience. The kitchenette has everything you need. The sleep loft is accessible by a ladder and has a low ceiling. Disclaimer there is no door on the toilet, which is tucked away in the kitchen area. WiFi connection is not guaranteed.

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.

Downtown Backyard Oasis

Enjoy easy access to everything from this perfectly located home base in downtown Plymouth. It is just a five minute walk to the 1620 Hotel, Mayflower, Plymouth Rock, beach, waterfront restaurants, Main Street boutiques & coffee shops, etc. Five minute drive to T station (in Kingston) for fun day trips to Boston without the traffic. Easy drive to Cape Cod for day trips as well! This newly renovated, yet charming, 2 bedroom first floor apartment is a perfect get away.

PLYMOUTH CENTER - The Captain's House #1

A true downtown gem. Sparkling clean PRIVATE 1,600 sq ft HOUSE. Unbeatable location with all that Plymouth has to offer literally outside the door - restaurants, the harbor and historic sites (yet on a quiet street). Stylish, renovated 5 bedroom, 2 full bathrooms, laundry, a huge front porch and hidden backyard courtyard. Full kitchen, dining room, and living room. Park 2-3 cars in driveway. Central AC. A guest favorite that rarely disappoints.

Remodeled Studio Apartment in Downtown Plymouth

Come experience the charm and rich history of “America’s Hometown!” Get transported back in time in an 1887 colonial home located in the heart of downtown Plymouth. Enter through the French doors into a recently remodeled studio apartment with a full kitchen, full bath and king-sized bed. All the modern comforts you could ask for in a quaint and cozy rental. Walking distance to restaurants, shopping, Plymouth Rock, the Mayflower and more!

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

Please do not book weekends, holidays, or summer dates in advance. This 1-bedroom is only offered to fill midweek gaps when the full home isn’t booked. Beautifully restored historic home in the heart of town—steps from the Pilgrims' first settlement, ocean, restaurants, shops, and more. Located on Town Brook near the Gristmill, with a deck, firepit, hot tub, grill, cozy bed, and working wood stove. Clean, comfortable, and full of charm.