Family-friendly holiday rentals in Charlestown

The Tree House at Underhill Hollow

The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.

Westerly Garden Apartment Minutes Walk to Downtown

Comfortable, spacious apartment walking distance to downtown Westerly with patio, outdoor dining and fire pit. Let DownWest Apartment be your landing pad to enjoy nearby beautiful ocean beaches, historic towns, renowned dining and casinos. Head to the United Theater or the Knick for a night of entertainment and dancing, hop the Amtrak for a night out in Mystic, CT or take a stroll through historic Wilcox Park. Or, grab some fresh lobsters to bring home and enjoy all that DownWest has to offer.

Salt & Stone House-1 bedroom Oasis sleeps 4

Downtown 1 bd, 1 bth unit. Park your car and walk downtown to shop, grab a bite to eat, catch a movie at the renovated United Theater or take a stroll in beautiful Wilcox park. This gem is in the heart of Westerly and only a 10min. drive to the beach. Finish your day on the back porch overlooking the fenced in yard. Can sleep 4. 1 bdrm with Queen bed and living room pullout full size bed. Grocery, Liquor, restaurants, laundromat are all steps away from this well kept secret on a dead end road.

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!

Serene Retreat apartment

This apartment has everything you'll need for a peaceful stay. Enjoy complete privacy in the apartment, hang out on the shared screen porch or deck, or luxuriate in a hot outdoor shower. The space is equipped for long stays, with a dedicated work space, full kitchen, washer, dryer, and storage space. Walk to the bike path or URI campus (we are 1.4 miles from the center of campus). Under 5 miles to Amtrak, stores and restaurants; less than 10 miles to beautiful beaches.

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

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.