House holiday rentals in Westport

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

PLEASE DO NOT BOOK WEEKENDS/HOLIDAYS/SUMMERS in advanced. I only use this 1 bed to fill gaps when the larger listing for this home isn't rented (mostly midweek) Beautifully restored historic home, directly in town, steps away from the Pilgrims 1st settlement, ocean, award winning restaurants, historic attractions, shops, nightlife, entertainment, tours,ferries, etc. Directly on the town brook/gristmill. Deck with view, firepit, hot tub, grill. Comfortable/clean/cozy bed, working wood stove.

Awesome 3 bed vacation lake house. Great location!

Three bedroom house right on Johnson’s Pond with private water access right in the back yard. House features queen master with deck overlooking the pond. 2nd bedroom features a full bed with twin bunk bed above along with a stand alone twin bed. 3rd bedroom has a queen bed. Perfect for one or two couples to share. Full kitchen and laundry along with WiFi and streaming services. Use of 2 kayaks and pedal boat. Just two miles from I-95, so everything in southern New England is just minutes away!!

NEW! 2 Houses, Main House plus Guest House

Two adjacent, fully renovated, houses! Main house (4 BR / 2 BA) and guest house (2 BR / 1 BA) on 3 serene acres with a privately owned cranberry bog. Let the adult kids have their own space in the guest house. These two houses are listed individually and here as a set. Perfect for large family gatherings, or to spend the summer holiday. Incredibly peaceful setting, 10 minutes from downtown, 10 minutes from Old Silver Beach, and central to everything. Come see this very special property.

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.

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

Walk To Town - Beautiful Edgartown Cottage

Walk to downtown Edgartown in minutes while staying in this newly renovated 2-story home in the heart of Upper Main St. The 3-bedroom, 2-bathroom house has been completely renovated, with brand new bathrooms, kitchen appliances, etc. You cannot beat the location of this home! You're a short 10 min walk from Edgartown's amazing restaurants & shops, in addition to a short bike ride to Katama's famous South Beach or Oak Bluff's State Beach. Both easily accessible via bike paths.

Lakefront Scenic: Your Perfect Getaway!

Escape to our serene lake house with breathtaking views & endless opportunities for outdoor adventure. With a dedicated workspace, stay connected while enjoying tranquility. Take a paddle on the lake with kayaks & pedal boat, or relax on the patio with outdoor fire pit. Fully furnished & decorated, feel at home cooking in the fully equipped kitchen or curling up in the cozy living room. Book your stay today and experience the magic of nature firsthand!

Salty by the Sea

Bright and charming home with the perfect gathering space...large, open-concept great room with water view. Ideal location just a few-minutes walk to historic lighthouse, town beach and quaint seaside village! Nearby bike path for scenic coastal rides. New heating and A/C for year-round comfort, outdoor shower and many more amenities. Picture-perfect rental for a quiet getaway or whole-family fun! We hope to welcome you soon!

Dreamy house in the woods. 3bdr/6beds/2.5ba

Welcome to our sun-drenched, newly updated New Seabury getaway with 3+ br, 2.5 baths and an outdoor shower. 15-minute walk/3-minute bike ride to the Spit beach. Short drive or a scenic walk to the Popponesset Inn/Marketplace. Enjoy our big private backyard setup with a hammock, patio and a cozy fire-pit. Relax on our expansive wrap-around deck equipped with a 4-burner Weber grill, dining furniture, and a patio set.