Holiday rentals in Kingston

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Top-rated holiday rentals in Kingston

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The entryway features a wooden staircase with white railings leading to the second floor. A cozy seating nook sits beside a window, adorned with decorative pillows. Light-colored walls complement the hardwood flooring, while a console table with a decorative bowl adds a welcoming touch.
Home in Plymouth
5 out of 5 average rating, 141 reviews

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.

Top guest favourite
A deck overlooks the bay, featuring two wooden lounge chairs positioned for relaxation. The tranquil water reflects the sky, with distant hills and boats visible on the horizon. The scene conveys a peaceful coastal setting, ideal for enjoying views of sunrises and sunsets.
Home in Kingston
4.84 out of 5 average rating, 109 reviews

Waterfront Rocky Nook Beach House

Waterfront 3 bedroom rental beach house on Plymouth/Duxbury/Kingston Bay, steps from private sandy neighborhood beach on quiet street. Area exceeds crowded Cape Cod for quiet vacation. Wake to fantastic views & sunrises on unique tidal bay; step out to the beach without packing a car! Downtown historic Plymouth has many new & upscale shops & restaurants, water sports; Cape Cod bridges 20 mi south, Boston 35 mi via nearby train, take ferry to Martha's Vineyard, Provincetown, Nantucket for a day

Guest favourite
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
4.92 out of 5 average rating, 353 reviews

Lionsgate at Cohasset

Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

Guest favourite
A view overlooking a well-maintained pool surrounded by green grass, with beach access visible in the distance. The landscape features a mix of trees and charming houses, set against a clear blue sky and tranquil water.
Home in Plymouth
4.9 out of 5 average rating, 301 reviews

Ocean Side, Amazing View, close to town/beach, Spa

PRICING IS FOR 2 GUESTS, 1 BEDROOM, 1 BATH ONLY, can add additional bed/bath for a fee, YOU WILL HAVE THE HOUSE TO YOURSELF. We only use this listing to fill gaps when the larger listing isn't rented & will decline ALL WEEKENDS, HOLIDAYS, PEAK times and will only accept mid-week, non summer/holidays. Please read additional info. OCEAN FRONT, HISTORIC SUMMER COTTAGE, AMAZING VIEWS, GREAT LOCATION, less than 1 mile walk to town and beach. Hot tub, fireplace, stocked kitchen, fresh linens.

Top guest favourite
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
4.94 out of 5 average rating, 170 reviews

The Gateway to Cape Cod Loft!

SUMMER 2026 is OPEN! November 4-30 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.

Top guest favourite
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
4.98 out of 5 average rating, 314 reviews

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.

Top guest favourite
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.
Flat in Falmouth
4.97 out of 5 average rating, 261 reviews

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

Guest favourite
A spacious grassy yard is bordered by tall trees, providing shade and a serene view of the lake. Sunlight glistens on the water's surface, and a small seating area is visible in the foreground, inviting relaxation in this picturesque outdoor setting.
Home in Pembroke
4.88 out of 5 average rating, 161 reviews

Lakefront House Boston, Plymouth, Cape Cod

Directly on the lake, with spectacular year round views. Perfect for a couple’s getaway or a family vacation. Its our family lake home where many special memories have been made & more are waiting! Home is about 15 minutes to historic Plymouth, 35 minutes to Boston, 20 minutes to coastal beaches, 40 mins to Cape Cod, 8 mins to Fieldstone show park & just 1 mile from the MBTA Halifax commuter rail station-takes you right into Boston or just stay & enjoy the lake. Private water access.

Guest favourite
A spacious room features a king-sized bed with a neutral quilt and decorative pillows. French doors open to a view of the outdoor area, allowing natural light to illuminate the space. A patterned area rug enhances the room's aesthetic.
Flat in Plymouth
4.91 out of 5 average rating, 159 reviews

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!

Guest favourite
A charming cottage is displayed, featuring soft yellow siding and blue shutters. A welcoming front door is framed by greenery, while neatly arranged stones lead to the entrance. The surrounding yard is lush, showcasing various plants and flowers, set against a peaceful backdrop of trees.
Cottage in Kingston
4.87 out of 5 average rating, 260 reviews

Classic New England Beach Cottage

NO CLEANING FEE! LESS THAN 5 MIN WALK TO THE BEACH Enjoy a fun and relaxing stay in Kingston, within a 10 min drive to the Plymouth waterfront, featuring Plymouth Rock, the Mayflower replica and many great restaurants and shops. Less than an hour to Boston and 30 mins to Cape Cod. Our cottage has a private back yard with a gas grill, patio for outdoor dining, an area for lounging & an outdoor shower. See our 200+ five-star reviews!

Top guest favourite
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.
Flat in Mattapoisett
4.98 out of 5 average rating, 132 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.

Guest favourite
The exterior of an antique home is showcased, featuring a sloped roof and neatly arranged windows with shutters. A brick pathway leads toward the entrance, bordered by manicured gardens and decorative planters. A vintage-style lamp post stands beside the path, adding charm to the welcoming front yard.
Guest suite in Plymouth
4.95 out of 5 average rating, 241 reviews

Comfortable & Historic Plymouth Suite

Our place is perfect for couples or single guests who are looking to enjoy Plymouth for all of the scenic and historic opportunities it has to offer. This space is part of our antique home, yet guests will be able to enjoy their privacy. We are centrally located between Plimoth Patuxet, Long Beach, and Downtown.

Popular amenities for Kingston holiday rentals

When is the best time to visit Kingston?

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Avg. price$170 SGD$163 SGD$163 SGD$196 SGD$237 SGD$261 SGD$228 SGD$228 SGD$200 SGD$196 SGD$196 SGD$170 SGD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Kingston?

    Kingston has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Kingston have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Kingston. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Kingston?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Kingston have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Kingston. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Kingston?

    Yes! Work meets play with ease at over 20 vacation rentals in Kingston featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Kingston have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Kingston. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Kingston?

    Make yourself at home in Kingston by choosing from our most frequently booked neighborhoods. We have over 160 vacation rentals in North Plymouth, over 10 vacation rentals in Island Creek Village, and over 20 vacation rentals in South Duxbury.

  • Do house rentals in Kingston have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Kingston. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Kingston

  • Total holiday rentals

    Explore 40 holiday rentals in Kingston

  • Nightly prices starting at

    Kingston holiday rentals start at $91 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,810 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Kingston holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kingston rentals

  • 4.9 Average rating

    Kingston stays are highly rated by guests – averaging 4.9 out of 5!