Family-friendly holiday rentals in Charlestown

Guesthouse in Charlestown

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.

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!

4.97 out of 5 average rating, 111 reviews

Tiny home in South Kingstown

A compact, waterfront tiny house features large windows that fill the interior with natural light and offer views of the serene salt pond. The modern kitchen area is equipped with essential appliances, while the sleeping area contains a spacious bed surrounded by warm wooden walls.

Waterfront Tiny House in Matunuck

Waterfront tiny house with dock access to the clearest salt pond in the state only 15 steps from the front door. Bring or locally rent kayaks or paddle boards to explore the pond, walk to one of the best beaches in RI, and pop next door to one of America's top rated oyster bars (rated #17 by Food & Wine) for a dinner with a view. Wind down with the sunset or keep the fun going with lawn or board games before snuggling up with a movie before bed. Come stay at the best kept secret in Rhode Island.

4.9 out of 5 average rating, 148 reviews

4.98 out of 5 average rating, 184 reviews

A spacious dining area is highlighted by a wooden table surrounded by elegant chairs. Natural light pours in through large windows, illuminating the inviting living space with a comfortable sectional couch and a wall-mounted TV. Decorative pendant lights enhance the modern kitchen's open layout.

Home in Westerly

Cheerful Cozy Colonial

Relax at this warm, welcoming, peaceful place to stay, with hiking trails nearby and only a 10-15 minute drive to various beaches, and a 10-minute drive to downtown Westerly. Set on 2+ acres, rejuvenate and connect with friends and family around the outdoor fire pit. Inside you will find a comfortable space with a full kitchen, living room, dining room, three bedrooms, and a full and half bath. Between Memorial Day and Labor Day, enjoy the outdoor shower after a long hike or trip to the beach.

Two Adirondack chairs are positioned near the water's edge, facing a tranquil pond. Sunlight reflects off the water surface, with a small table placed between the chairs. Lush greenery and a tree provide a serene backdrop.

4.99 out of 5 average rating, 183 reviews

Waterfront Secluded Home with Dock

Nestled down a private road, enjoy a lovely waterfront home with sweeping 180 degree views of Potter’s Pond. Newly renovated and meticulously decorated. Unwind and relax on the back deck watching the extensive variety of birds and breathtaking sunsets. Spend your days exploring the pond in kayaks or try your hand at clamming, steps from the house. Located 1 mile from East Matunuck Beach, 1 mile from Tennis, Pickleball and Basketball courts. Walking distance to the renowned Matunuck Oyster Bar.

Guesthouse in Charlestown

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.

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.

4.88 out of 5 average rating, 347 reviews

An aerial view showcases a coastal home surrounded by lush green lawn with the Atlantic Ocean visible in the distance. The shoreline curves gently along the property, while neighboring homes are positioned nearby. A serene atmosphere characteristic of the Matunuck Point area is presented.

4.99 out of 5 average rating, 118 reviews

Unique Home with Panoramic Ocean and Pond Views

A unique and tranquil getaway, described beautifully by client reviews. Situated on Matunuck Point with sweeping views of the Atlantic Ocean, beautiful Block Island, boats coming in and out of historic Galilee Breach Way or enjoy watching surfers at Deep Hole. Love the beach? We have private access to East Matunuck 100 steps away. If your preference is the pond, Potters Pond is right in the back yard with a new beautiful custom built dock, with paddle boarding, and kayaking equipment.

4.97 out of 5 average rating, 146 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!

5.0 out of 5 average rating, 175 reviews

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

Sunny Days, Starry Nights | 10 Min to Beaches

☀️ WESTERLY BEACH PASS INCLUDED ☀️ Welcome to Woodhaus Westerly — Minutes to both Westerly and Charlestown beaches, downtown shops, breweries, and coastal walks. Enjoy a crisp beverage on the front porch swings, cool off in the outdoor shower then take in the stars after dark while enjoying an evening bonfire. Dog + kid friendly with plenty of space to relax. Perfect for couples and families - designed for making summer memories. View more photos and updates @Woodhaus_Properties

4.9 out of 5 average rating, 204 reviews

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

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.

The image showcases a serene waterfront view featuring a sandy beach area lined with greenery and blooming flowers. Calm waters reflect the sky, while boats are anchored nearby. The backdrop includes urban structures, providing a contrast to the natural landscape.

4.99 out of 5 average rating, 121 reviews

Charming Waterfront cottage

The charming waterfront home is directly across the street from a small private beach. Perfect area for families with young children. Private entrance to East Matunuck beach is just a two minute walk down the street. There is ample parking for 3-4 cars . This house has 1 queen size bedroom and one twin with trundle on the lower level (both bedrooms with TVs). The lower level also houses the living room with large screen TV, full bathroom, kitchen and laundry.

The kitchen features a large quartz island with seating, surrounded by dark cabinetry and stainless steel appliances. Two pendant lights hang above the island, while ample natural light filters through the window, illuminating the modern design.

5.0 out of 5 average rating, 102 reviews

Coastal Paradise Stunning Water View Walk to Beach

Stunning 8BR Beach House: Water Views, Decks, Walk to Beach! This beautiful 3-story, 8BR, 4.5BA retreat is a short stroll to the beach. Enjoy phenomenal water views from two large decks. The second floor hosts the kitchen, dining area, and living room, opening onto the deck. Kitchen features a massive quartz island, stainless steel appliances, and hardwood dining table seating 12. The living room boasts a large sleeper couch and 65" 4K HD TV.

4.9 out of 5 average rating, 118 reviews

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

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!

Popular amenities for Charlestown family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An aerial view captures the proximity of the home to the beach, with a path highlighted leading from the property to Scarborough Beach. The coastline is visible in the background, along with a parking area and neighboring homes.

4.96 out of 5 average rating, 101 reviews

Ocean view, walk to beach, backyard oasis

4.89 out of 5 average rating, 112 reviews

Home in Westerly

FREE Heated Swim Spa, Pool Table, BBQ

4.97 out of 5 average rating, 262 reviews

An aerial view showcases a traditional New England-style home with a distinct green roof. A private pool with steps is situated on a spacious deck, surrounded by lounge chairs and tropical plants. Scenic outdoor areas for relaxation and recreation are visible on the property.

Home in Stonington

Perfect New England Getaway has a pool/ hot tub

Chalet in North Kingstown

A bright living area is feature with a white sectional sofa and a round coffee table. Natural light filters through multiple skylights and windows, highlighting the exposed brick wall with a fireplace. A serene atmosphere is created, complemented by a few decorative plants.

Wickford Beach Chalet Escape

4.89 out of 5 average rating, 357 reviews

The living area features a light-colored sofa with striped accents, accompanied by two patterned armchairs. A wooden coffee table is centered on a textured area rug, while two windows allow natural light to fill the space. A ceiling fan is positioned above for comfort.

4.95 out of 5 average rating, 134 reviews

Cozy SK Cottage

4.97 out of 5 average rating, 156 reviews

A charming two-story house features a shingle exterior and large windows, providing ample natural light. Lush green grass surrounds the home, complemented by mature trees offering shade. A small front porch with white chairs invites relaxation while enjoying the serene landscape.

Home in Stonington

Unobstructed Water Views & Huge Patio with Hot Tub

Guest suite in Stonington

Morgan Suite - spacious | hot tub | water views!

4.98 out of 5 average rating, 396 reviews

4.97 out of 5 average rating, 204 reviews

A vibrant backyard features a spacious pool with clear blue water, complemented by a wooden deck and a shaded seating area under an umbrella. The two-story house stands in the background, surrounded by greenery, creating a peaceful outdoor environment.

Home in Montville

Casino Stay & Play House w/Hot Tub, Game Room

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 142 reviews

A serene view of the home surrounded by lush greenery and blooming trees, reflected in the calm waters of the nearby pond. The property is framed by tall trees, creating a peaceful atmosphere in the rural setting.

Home in Hopkinton

Estate with lake near beaches & Westerly

A charming house is set against a clear blue sky, surrounded by lush greenery and blooming flowers. The wrap-around deck is visible, inviting outdoor relaxation. The landscape includes well-maintained shrubs and a stone wall, enhancing the home's curb appeal.

4.94 out of 5 average rating, 116 reviews

Ocean views! Scarborough Beach, Narragansett, RI

A cozy home is presented, featuring a welcoming front porch with steps leading to the entrance. Surrounded by well-maintained shrubbery and trees, the structure's light exterior contrasts with the lush green lawn, creating an inviting outdoor space.

5.0 out of 5 average rating, 136 reviews

Momma Bears Bungalow

A spacious front porch features contemporary outdoor seating with scenic views of the ocean. The deck is surrounded by a low railing and includes a table, inviting relaxation while enjoying the coastal surroundings. Lush greenery and a pathway are visible beyond the porch.

4.98 out of 5 average rating, 148 reviews

The Surf Shack - Ocean Views From Every Room

4.99 out of 5 average rating, 158 reviews

Simple Cottage-Pet Welcoming + Beach Pass Included

4.96 out of 5 average rating, 170 reviews

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

Room with a View on Spring Pond

4.93 out of 5 average rating, 132 reviews

A charming white cottage is surrounded by lush greenery and vibrant orange lilies in the foreground. The entrance features a decorative wrought-iron railing, set against a backdrop of tall trees and an inviting garden, creating a serene outdoor atmosphere.

Cottage in Westerly

Romantic water view cottage - CASITA AL MAR

4.95 out of 5 average rating, 748 reviews

A camp cottage exterior is shown, featuring a wooden facade with a red trim. Two rocking chairs are situated on the porch, inviting relaxation. Multiple windows allow natural light to enter, and a pathway leads to the entrance among the surrounding trees.

Cabin in Voluntown

Ellis -Lakeside Cabin on Beach Pond with Sauna

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 153 reviews

A two-story house is framed by lush greenery and vibrant flowering shrubs. The exterior showcases a combination of brick and wood, with multiple windows allowing natural light to fill the interior. A clear blue sky with scattered clouds completes the picturesque setting.

Home in Exeter

Nature's Nook

4.96 out of 5 average rating, 110 reviews

A serene scene is captured as the in-ground saltwater pool reflects the evening sky. Lounge chairs are aligned beside the pool, while the house showcases warm lights glowing through large glass doors, offering a welcoming view of the outdoor entertaining area.

Home in Middletown

Heated Salt Pool | Near Newport, Beaches | Pkg 4 6

4.92 out of 5 average rating, 215 reviews

An open living area features a modern sectional sofa facing a coffee table, with light-colored tiled floors and large windows letting in natural light. The space includes a dining area with tall chairs visible in the background, offering views of the outdoors.

Home in New London

Sunset Oasis 1 @ Ocean Beach: $1Mil View 6 Queen

4.87 out of 5 average rating, 141 reviews

Aerial view of a spacious home surrounded by lush greenery, showcasing a large pool with a deck. Solar panels are visible on the roof. The property is set in a serene wooded area, providing a sense of privacy and tranquility.

Home in Stonington

Mystic Woods Homestead | Pool, Hot Tub, Casinos

4.92 out of 5 average rating, 131 reviews

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

Breathtaking home with unforgettable views & pool!

4.91 out of 5 average rating, 257 reviews

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

4.91 out of 5 average rating, 253 reviews

A serene bedroom features a spacious bed adorned with white bedding and decorative pillows. Nightstands with lamps flank the bed, and a cozy couch with patterned cushions offers additional seating. Natural light filters through sheer curtains, enhancing the calming environment.

Condo in Norwich

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf