Family-friendly holiday rentals in Charlestown

Heathers On High Street King Bed/Twin Bed

Experience Westerly life like a Local! Enjoy this centrally-located Apartment close to Downtown. Easy highway access to the Beach and Casinos. Free Parking with Private entrance opens to a courtyard with Gazebo Sitting area and a Grill just for you! The 2 Bedroom Apartment is located on the 2nd floor with a Full Kitchen/Living Room combination, 1 Bathroom, Washer/Dryer and Central Air. The Master Bedroom has 1 King Bed with a new Nectar Mattress. Second smaller bedroom has a Twin Pillowtop Bed

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.

Heart Stone House

This peaceful and centrally-located place is a sunny and spacious modern one-bedroom cottage located in the heart of historic Wakefield. We're minutes from many RI beaches. Stroll downhill to a lovely park on Saugatucket River, then cross the charming footbridge into town. Here you'll find a variety of restaurants, cafes, and ice cream, plus excellent community theater, yoga, and interesting shops. Relax inside this light-filled home or sit out on the deck overlooking the gardens and town.

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.

Sunny Wakefield studio apartment

Attached to a family home but its own private space—including a private entrance, dedicated parking space, small deck, and lawn area with seating—this sunny studio is in the walkable heart of Wakefield, near URI, beaches, Newport, bike path. Queen bed; queen sleeper couch; best suited to 2 adults (the sleeper couch works best for children). Fridge, micro, coffee, grill (no oven). Allergy friendly: Free & Clear laundry products; no pets. Self check-in. Automatic discount for longer stays.

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!

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. In the warmer weather, enjoy the outdoor shower after a long hike or trip to the beach.

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.

Private suite close to beaches and downtown.

The Ruedemann Suite is situated off of our main house in a quiet neighborhood. We are located 3 miles from Misquamicut Beach & Watch Hill. Historic Downtown Westerly with its thriving restaurant, arts & music scene is 1.5 miles from the house. Take a short drive to Stonington or Mystic for shopping or local vineyards. Feeling lucky? Mohegan Sun & Foxwoods Casinos are close by! Newport & Providence are a 45-minute drive. Follow on the gram @ruedemannsuite

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.

Cute Little House in Town

Cute little guesthouse perfect for two people, but could also work for three with advance notice. There is a queen bed upstairs, and a couch downstairs, there are two fold out cots available upon request. The deck overlooks the huge backyard. The television has a Roku boxes so you can watch Netflix, Amazon Videos, etc. I have a friendly dog named Barney who is often outside on the property.

Westerly Gap

Westerly Gap is a lovely private unit located in a quiet, residential neighborhood a mile from the Rhode Island coast. Close to some of the most beautiful beaches the Northeast has to offer. A private outdoor sitting area, outdoor shower and comfortable living space make this the perfect spot for your relaxing beach vacation. Take it easy at this unique and tranquil getaway.