Family-friendly holiday rentals in Charlestown

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!

Family · Indoor spaces · Nearby

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.

Indoor spaces · Kitchen · Checkout

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.

Indoor spaces · Family · Decor

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.

Kitchen · Indoor spaces · Quiet

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.

Indoor spaces · Kitchen · Check-in

The Surf Shack - Ocean Views From Every Room

This home was featured in the June 2021 issue of SO RI magazine! Located on a quiet cul-de-sac this home has a welcoming front porch with ocean views, an open concept family room w/ fireplace, a spacious eat-in kitchen and a park-like backyard. Private beach connects to Scarborough State Beach. There are 3 king bedrooms and a separate kids room. Master bath has a jacuzzi tub and 2nd bath has a standing rain shower with sprawling marble sink. House has towels, beach chairs and bikes.

Family · Kitchen · Outdoor spaces

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

Indoor spaces · Family · Location

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.

Kitchen · Family · Pets

Beach Getaway

Enjoy all that Charlestown has to offer! This charming 3 bedroom, 2 bath home is the perfect spot for your beach getaway. Enjoy the summer weather with the outdoor dining area, backyard and screened in porch. A bedroom with twin beds is off the main floor, and upstairs a bathroom connects two bedrooms, one with a full bed and and the other a queen bed. Charlestown Beach is a 5 min drive, beach parking pass included. Close proximity to local farm stands, eateries and more!

Family · Kitchen · Barbecue

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.

Kitchen · Indoor spaces · Backyard

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.

Family · Kitchen · Decor

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!

Indoor spaces · Kitchen · Barbecue