House holiday rentals in Plymouth

Freshwater Cottage - 1 min walk to private beach

Welcome to Freshwater Cottage, our home is designed with comfort and relaxation in mind, offering a perfect blend of modern amenities and rustic charm. Whether you're looking to escape the hustle and bustle of daily life, enjoy quality time with your family and explore the beauty of the surrounding landscape. Our retreat is located in a quiet neighborhood 3 houses from Sandy Beach and Wall Pond and 4 minutes to fully recreational Big Sandy Pond with private association beaches and boat landing.

Updated Antique in Historic Downtown Plymouth

Updated antique colonial within walking distance to everything historic Downtown Plymouth has to offer- waterfront, boating, shops, restaurants, historic sites, and more. Fenced in backyard with patio overlooking gorgeous, well-maintained garden. Patio has large farm table with umbrella and Weber grill, great for entertaining! This charming in-town location offers you the best of both worlds - walking distance to everything while also being cozy and comfortable to enjoy a day at home to relax.

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.

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.

Fall In New England, Book Today!

Fall is a great times to visit Plymouth, from leaf peeping to Cranberry Harvesting and chilly Fall Festivals, we have it all! Our location is walkable and super safe, and you'll be in the heart of it all. We are less than a block from many beaches, restaurants, nightlife and historical tours. Check out our walk-through video on You Tube. Type WhaleTailInt 2019 in the search for a virtual tour of the entire house. Hop on the "T" and day trip to Boston, Cape Cod or even New Hampshire!

Ocean view home on Cape Cod Bay

Welcome to this family beach home on a 150-foot cliff with breathtaking views over Cape Cod Bay. This is one of the highest oceanfront locations on the entire East Coast. The airy, open living space has an ocean view, including the kitchen. Relax on the spacious screened porch. Take day trips to Plymouth, Boston, Cape Cod, and the islands. Have a picnic in the private cliff garden, and take in the vast, blue expanse below. This is an incredibly peaceful place, with so much to do nearby.

Pet Friendly 🐶 …Walk to White Horse Beach

Be our guest …Enjoy the coastal charm of Plymouth , America’s hometown, 3BR (main bedroom en-suite) 2 Bath home in a family friendly residential beach community. “Coastal Soul” is a short walk to White Horse Beach and our pet friendly private beach access. Create memories with family and friends around the fire pit on the large deck and private backyard. Perfect backdrop and central base camp to explore Massachusetts’s historic sites and coastal beauty.

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & a fire pit. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod.

The Captain's House - Downtown Plymouth

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.

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.

1 of a Kind Pond-Front Home, Minutes from Downtown

Pond-Front property boasts unparalleled privacy and charm. 5 minutes from shopping and downtown Plymouth. Located on a peninsula of land, water views are plentiful. Both ponds are tested yearly and safe for swimming, fishing, etc. Bring your furry friend to run in the back yard, your kids to play, or simply your friends to relax and catch some sun. Opportunities are endless!

Oceanfront | Firepit | Gameroom | Pets | Kayaks

Welcome to Beach Bliss—AS SEEN ON THE EMMY AWARD WINNING TV SHOW - STAYCATION! This newly renovated 5BR, 2BA waterfront retreat in Buzzards Bay offers a fire pit, game room, modern amenities, and cozy charm. Walk to local restaurants and attractions, or relax with breathtaking views. The perfect escape for comfort, style, and tranquility on Buttermilk Bay.