Family-friendly holiday rentals in Charlestown

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Charlestown

  • Total holiday rentals

    Explore 150 holiday rentals in Charlestown

  • Nightly prices starting at

    Charlestown holiday rentals start at $128 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,520 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    150 of Charlestown holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Charlestown rentals

  • 4.9 Average rating

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

Top-rated family-friendly rentals in Charlestown

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A bright living room features large windows allowing natural light to fill the space. Two colorful wall art pieces adorn the light blue walls. A comfortable seating arrangement includes a white sofa and wicker chairs set around a coffee table, creating an inviting atmosphere.
Guest house in Charlestown
4.97 out of 5 average rating, 102 reviews

Spacious and serene 2-bedroom ~ Close to beaches!

“The Nest” is a spacious, serene 2 bedroom apartment built above our stand alone storage garage. Upon entering the 1000 sq ft space you are greeted with an open floor plan boasting cathedral ceilings, modern wet bar/kitchenette, bright living room and dining area. Sliders open to private deck with wooded view. A full bath, 2 bedrooms and add’l sleeping nook off the main living area complete the space. Also on the property are a cottage and 1800s Colonial home. Close to beaches, URI & more!

Top guest favourite
A spacious kitchen features a large island with intricate granite countertops and an integrated cooktop. Elegant dining chairs surround a rustic table, while large windows provide a view of the lavender field. Wood paneling and a flat-screen TV add warmth to the inviting atmosphere.
Farm stay in South Kingstown
4.99 out of 5 average rating, 372 reviews

Lavender Farm Private Luxury Suite

The luxury suite features reclaimed wood from a 150 year old silo. Reclaimed beams adorn the ceiling. The shower features rainfall, waterfall and massage jets. There is a four post king size reclaimed wood bed with an amazing second floor view of the entire circular lavender field. There is also an open kitchen/living room area with a view of 4,000+ lavender plants. You will be surrounded by custom-picked imported Italian granite selections. The sinks in the suite feature amethyst geodes.

Top guest favourite
An inviting living space is characterized by high post and beam cathedral ceilings, with a floor-to-ceiling fieldstone fireplace as a focal point. Cozy seating is arranged around a central coffee table, with warm lighting provided by string lights. The area reflects a blend of rustic charm and modern comfort.
Cabin in Westerly
5 out of 5 average rating, 168 reviews

Sunny Days, Starry Nights | 10 Min to Beaches

WINTER GETAWAY ALERT: Cozy up on the RI Coast! Welcome to Woodhaus Westerly — a peaceful winter retreat minutes from downtown shops, breweries, and coastal walks. Enjoy 3 private wooded acres for starry-night bonfires, winter trails, and cozy nights by the wood stove with blankets, games, and movies. Dog + kid friendly with plenty of space to relax. Perfect for couples, families, or a remote-work refresh. ☀️Beach Pass returns for Summer 2026! View more photos and updates @Woodhaus_Properties

Top guest favourite
The cottage is surrounded by vibrant greenery and colorful flowering shrubs. A tall American flag waves in front of the charming structure, which features a blue door and windows framed by shingle siding. A white picket fence enhances the quaint curb appeal of the home.
Cottage in South Kingstown
4.94 out of 5 average rating, 138 reviews

The Snug Cottage: Walk to Water-Newly Renovated

Simply adorable studio cottage. 216 sq.ft. Central AC & heat, kitchen w/stove, oven, refrigerator, sink, & cabinets. Outfitted w/ plates, dishes & cookware. Eating area w/ drop leaf table. Comfortable, memory foam double bed w/ storage bins underneath. Bathroom w/ shower stall & pocket door. An outdoor shower for an easy post beach rinse too. No smoking in or on the premises. 2 parking spots at property; NO BOATS, RVs/TRAILERS ALLOWED ON PROPERTY . No street parking. No candles. RE-01712-STR

Top guest favourite
A charming cottage exterior is surrounded by lush greenery, featuring a patio with a shaded table and chairs. A gas grill is positioned nearby, and large windows provide a view into the cozy interior. The patio area invites relaxation amidst the tranquil outdoor setting.
Cottage in South Kingstown
4.99 out of 5 average rating, 135 reviews

A very special beach cottage in the country

Our beach cottage in the country is located on a dead end country road and looks out over a beautiful meadow, part of an abutting farm. It is within walking distance from the quaint New England main street of Wakefield where you will find many shops and restaurants. You are also within 10 minutes driving distance to many beautiful beaches, a short drive to Newport and a ferry ride to Block Island. You can have all kinds of seaside adventures while coming home to your quiet country cottage.

Guest favourite
The exterior of the vintage cabin features a welcoming porch with two green chairs and various potted plants. The cabin has a clean, white facade with dark doors, surrounded by a lush green lawn and trees, inviting a sense of tranquility.
Guest house in Charlestown
4.88 out of 5 average rating, 328 reviews

Cozy All Season Cabin Near Beach at Rockbriar Farm

Small vintage vacation cabin located in Charlestown, RI a 1 mile walk/bike to the town beach. Located on 7 acres called Rockbriar Farm, the cabin is in a wooded setting away from our home affording privacy for guests. One large room includes the futon bed/couch and the one sink; the shower and toilet are in separate room. Cabin also has a cedar enclosed hot water outdoor shower. Clean, cozy but not luxurious! No stove, but coffee maker, microwave, outside grill, and mini fridge.

Top guest favourite
A tranquil outdoor scene features four white lounge chairs arranged under a striped umbrella by the water's edge. A wooden dock extends into the calm water, surrounded by lush greenery and a scenic sunset sky filled with soft clouds.
Home in South Kingstown
4.98 out of 5 average rating, 136 reviews

Stunning Waterfront Cottage with Big Yard & Dock!

Escape to the tranquil beauty of "A Summer Place," a charming 1,500 sq ft waterfront cottage nestled just steps from RI's stunning coastline and pristine beaches. Whether you're planning a family getaway or a retreat with friends, this idyllic home offers the perfect blend of rural charm and modern amenities, all in a prime location near local shops, bakeries, cafes, and top-rated restaurants. The expansive yard and private dock provide an unbeatable setting while you sit back and relax!

Top guest favourite
A bright living space features a white brick fireplace, complemented by a black fire screen. Above the mantel, a large, minimalistic artwork with a sun motif is displayed. Shelving holds neatly stacked firewood and decorative items, enhancing the room's inviting ambience.
Home in Westerly
4.98 out of 5 average rating, 125 reviews

South County House

South County House is a 1500 sq ft two bedroom, 1.5 bath cape built in 1936 that sits on nearly an acre of land, 3/4 of a mile from the ocean in Westerly, RI. It borders preserved forest, and there is a small family farm across the street. The house has been thoughtfully redesigned and renovated with relaxation in mind, and provides an ideal escape from the distractions and noise of modern life. Recently featured in Vogue, Architectural Digest, Travel + Leisure, Remodelista, etc.

Superhost
An open living area features a blue sectional sofa positioned near a wooden coffee table. Natural light brightens the space from windows above the kitchen, where bar stools line the counter. A ceiling fan and decorative artwork accent the high ceilings.
Home in Charlestown
4.9 out of 5 average rating, 197 reviews

Spacious RI Beach Escape

Super-cute 3 bedroom, 2 bathroom house with big yard, deck and enclosed outdoor shower. Located on a quiet cul-de-sac just minutes from Charlestown Beach and walking distance to local restaurants and shops. Beautiful sunroom just off the kitchen provides bonus living space. There are multiple spots to comfortably work from home with strong connection for video calls. New Casper mattresses in every bedroom. Perfect for family vacation, a weekend with friends or a long-term stay.

Top guest favourite
A stone staircase descends towards a serene pond, bordered by lush greenery and vibrant hydrangeas in bloom. The calm water reflects the surrounding trees, creating a peaceful natural setting.
Guest suite in Westerly
4.96 out of 5 average rating, 159 reviews

Room with a View on Spring Pond

Fab newly decorated suite in 1957 home set on a private pond near Watch Hill, RI. Private entrance with mini kitchen, fridge,microwave, portable induction cooktop,toaster,coffeemaker- every thing but the kitchen sink! Please note: there is no kitchen sink nor oven. Ensuite bath with new towels,robes,linens,and bedding. Outdoor shower ( in addition to an indoor one!) ,grill,lounging area. Near beaches,music,food, Mystic Ct attractions. Great relaxing venue.

Guest favourite
A waterfront view features calm blue waters extending towards the horizon, framed by a white railing. The sky above is dotted with fluffy clouds, complementing the serene landscape of the pond and surrounding vegetation.
Home in Charlestown
4.91 out of 5 average rating, 111 reviews

Cozy cottage on the water

Escape to our idyllic, air conditioned beach house nestled by Green Hill Pond! Just a quick kayak or bike journey to the beach. Embrace tranquility by the saltwater pond, connected to the ocean. Enjoy essentials nearby - bakery, restaurant, ice cream shop, and grocery store. Begin your day with breakfast on the waterside deck, kayak to the beach, and unwind with serene pond vistas. Dive into a beach escape like no other – book now!

Top guest favourite
A charming two-story house is situated amidst greenery, featuring a welcoming front porch with black chairs. The exterior showcases light yellow siding and dark blue shutters. A gravel pathway leads to the entrance, surrounded by lush trees and grass.
Home in South Kingstown
4.97 out of 5 average rating, 204 reviews

Cozy beach house close to beaches with Fire Pit

Escape to our recently renovated (May 2023) beach house! This bright, 3-bedroom home comfortably sleeps your group with king, queen, and bunk beds. Features a modern kitchen, two pristine bathrooms, and a bonus lower-level playroom with a TV and toys. Perfectly located just a 5-minute drive from local beaches, nature reserves, and shops. Ideal for families and groups seeking a coastal adventure.

Popular amenities for Charlestown family-friendly rentals

When is the best time to visit Charlestown?

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Avg. price$323 SGD$396 SGD$397 SGD$396 SGD$447 SGD$447 SGD$511 SGD$512 SGD$452 SGD$415 SGD$407 SGD$384 SGD
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