Holiday rentals in Weekapaug, Westerly

Private chic waterfront retreat-newly renovated.

NEWLY RENOVATED CHIC WATERFRONT FAMILY RETREAT The perfect getaway spot! This newly renovated 3bed/2.5 bath gem sits on 1+ secluded acres on pristine Winnapaug Pond and Weekapaug golf course. A perfect place to enjoy the day exploring the backyard salt pond (kayaks, paddle boards, canoe incl) or sticking your toes in the sand and sea (5 minutes away. Weekly summer rentals only accepted as a Saturday to Saturday stay. 10 min to historic Watch Hill 25 min to Foxwoods. Don't miss out. Book now:)

Value · Family · Condition

Sweet Retreat Circa 1900 Restaurants, Park, Beach

Beautiful beach town 2nd floor self contained apartment in antique home! Perfectly located - a short walk to downtown cafes, park and 10 mins. to Westerly beaches. Quiet residential neighborhood. 3 bedroom apartment with ac & heat - kitchen, living room, bath and lovely porch. Mini splits & ceiling fans in BRs Zero contact entry. Family friendly! The first floor owner occupied. Close to casinos, Mystic, Newport, Prov. Stonington, Narragansett, URI and to the best beaches on the East Coast!

Family · Location · Nearby

3BR Beach House w/Private Beach!

Enjoy your beach vacation at this spacious 3 BR beach house and the PERFECT location... directly across the street from our own private beach. Simply park your car at the house and walk across the street to the beautiful private beach! It's ideal for your family vacation gatherings. Just pack your bed linens (sheets) bath + beach towels and beach supplies, and the rest is all here for you! Comforters and pillows are provided. Family-friendly neighborhood and lots of fun activities close by.

Value · Location · Access

Bird's Eye View Waterfront Unit

Bird’s Eye View is a private waterfront apartment occupying the entire third floor of our historic house in the Weekapaug area of Westerly. The property sits at the end of Winnapaug Pond, one of the area’s most stunning salt ponds and home to a rich variety of local and migrating wildlife, particularly aquatic birds. Our property is a 15 minute walk to the oceanfront and short drive to downtown Westerly, a vibrant hub with eclectic dining, small boutiques, live music and cultural events.

Location · Family · Cleanliness

The Lighthouse Chalet!

Welcome to our Lighthouse Chalet! Just 1/2 mile from the Misquamicut shore with private access, it's perfect for families or small groups. Our home sleeps six and has a fully equipped kitchen. Stay cool with a breezy front deck, shady backyard, and central AC. With parking for 4 cars, you're set for convenience. -Watch Hill is just a 5-minute drive away, making this the ideal spot for both relaxation and adventure! -URI, the Coast Guard Academy, and Connecticut College are also nearby!

Location · Family · Back garden

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

Value · Family · Amenities

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.

Value · Family · Bathroom

Charming Dunn’s Corners (Westerly) Cape

This deceptively spacious Westerly cape is ready for the families large and small! Centrally located in Dunn’s Corners, the home is less than 2 miles from “town” and all state beaches, and less than 5 miles from Watch Hill. The enormous deck and yard are ideal for outdoor gatherings. Dining room has huge cafe height table. Second floor master bedroom suite sleeps 6. Full Kitchen. Outdoor shower keeps the sand out! RI RE.01692-STR (Rhode Island) STR-22-357 (Town of Westerly)

Location · Value · Decor

Quanni Cottage

Brand new, fully renovated beach cottage located 1.4 miles to the stunning Westerly, RI beaches. This home features an open floor plan and sleeps 8-10 comfortably and is furnished with Pottery Barn and West Elm decor. Three bedrooms (K, K, twin over twin bunk and twin with trundle), two full bathrooms and one full size sleeper sofa. Features include gas fireplace, outdoor fire pit, grill, coffee maker, fully stocked kitchen, ping pong table and beach equipment.

Family · Location · Beach

The Oyster Shell

Designed with beach lovers in mind, ‘The Oyster Shell’ is ready to accommodate you on your next trip to Westerly! Our bright and airy vacation home has 3 bedrooms, 2 bathrooms, a deck with an outdoor shower, and a spacious open yard — close to many area beaches, including free access and parking during the summer months at Dunes Park beach (only 1 mile away). Your perfect spot close to many local attractions and activities for everyone to enjoy.

Value · Family · Nearby

Coastal Farmhouse

Escape to this beautifully renovated coastal farmhouse, tucked among peaceful woods yet just 5 minutes to the beach (pass available), country club, and scenic wildlife refuge. Bright open spaces, gleaming hardwoods, and room to gather make it perfect for creating lasting memories. Only 10–15 minutes to charming Watch Hill. Relax, unwind, and experience the best of coastal Rhode Island. 🌿 Woodland privacy. Coastal charm. Minutes to everything.

Family · Location · Decor

Westerly Gap

Westerly Gap is a lovely private suite. 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.

Location · Value · Sleep quality