Family-friendly vacation rentals in Watch Hill, Westerly

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Top-rated family-friendly rentals in Watch Hill, Westerly

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Hopkinton

4.88 out of 5 average rating, 120 reviews

Large estate with pond near beaches

Let this be your home away from home. Large, open, and upscale, with a cozy mix of comfort & nostalgia. Enjoy time with family and friends in our spacious, welcoming home on 40 beautiful acres - surrounded by fields, orchards, woods, stone walls, and large pond with kayaks & paddle boards. Great for family vacations, reunions, retreats, & celebrations. Weddings welcome - contact owner for details. Pet friendly. Close to RI beaches. 5 min. to I-95. 35 min. to Providence airport. 4 night minimum.

Guest favorite

Guesthouse in Charlestown

4.88 out of 5 average rating, 296 reviews

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.

Guest favorite

Guest suite in South Kingstown

4.95 out of 5 average rating, 178 reviews

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.

Guest favorite

Home in Stonington

4.96 out of 5 average rating, 185 reviews

Romantic Seaside Cottage in Mystic

This cozy seaside cottage with sleep loft has the look and feel of an old classic yacht inside with modern amenities. Couples will love the water views, screened porch, gas-wood stove, heated stone floor in cedar bathroom, outdoor shower and patio. Another larger 2 bedroom cottage on property is for rent also for families with younger children. This rental is NOT suitable for toddlers or children under 12 due to the open balconies, railings and narrow spiral staircase to the loft.

Guest favorite

Cottage in Ledyard

4.9 out of 5 average rating, 166 reviews

Waterfront cottage overhanging the water!

Come relax at this cute and cozy cottage overhanging a large and beautiful lake! Whether it's a family trip, a couple's getaway, or a best friends reunion, this place has something for everyone. From relaxing on the deck with a beautiful view, to kayaking and canoeing, or swimming in the summer, there is much fun and peaceful relaxation to do at the cottage. Also, it's just a 10 minute drive to Mystic, wineries, orchards, the shoreline, restaurants, and 5 minutes to Foxwoods casino.

Guest favorite

Home in Stonington

4.97 out of 5 average rating, 209 reviews

Perfect New England Getaway has a pool/ hot tub

traditional New England style that is not just a great home, but a great vacation compound with lots of amenities and outdoor living spaces. Enjoy recreational activities on land and sea that abound locally. Mystic, Stonington Borough, Westerly, and Watch Hill are all close IMPORTANT INFORMATION: Please be advised Stonington, CT has a STRICT OUTSIDE Noise ordinance after 10pm that is enforced by the Police. If a report is generated for any reason , you will forfeit your deposit.

Guest favorite

Cabin in Voluntown

4.94 out of 5 average rating, 633 reviews

Ellis -Lakeside Cabin on Beach Pond with Sauna

"Ellis" is a cute fully heated and winterized camp cottage built in the 1960's by the students of Ellis Tech. It has two bedrooms and sleeps 5. The detached bunkhouse has 3 single beds and is available for larger groups (summer only) Very peaceful lakeside location just 238 feet from Beach Pond. Walking distance to trails. Enjoy the quintessential lakeside vacation! This is not a secluded space so make sure to look at the photos to see the layout of other nearby buildings.

Guest favorite

Guest suite in Westerly

4.96 out of 5 average rating, 140 reviews

Room with a View on Spring Pond

Fab newly decorated suite in 1957 home set on a private pond near Watch Hill, RI. Private entrance with mini kitchen, fridge,microwave, portable induction cooktop,toaster,coffeemaker- every thing but the kitchen sink! Please note: there is no kitchen sink nor oven. Ensuite bath with new towels,robes,linens,and bedding. Outdoor shower ( in addition to an indoor one!) ,grill,lounging area. Near beaches,music,food, Mystic Ct attractions. Great relaxing venue.

Guest favorite

Cottage in Charlestown

4.89 out of 5 average rating, 154 reviews

Pet-Friendly Private Beach Oceanfront Cottage A/C

Azure Cottage is traditional cedar shingled cottage directly on the private beach in Charlestown, RI with stunning views of Block Island Sound. With two bedrooms and a large queen loft, the cottage sleeps 6. Doggie guests are welcome for an amazing off-the-leash beach vacation. Handheld showers on stairs make washing sandy feet and paws a breeze. Why wait? Book now to reserve for your best summer vacation ever! Pet fees are $30/day per animal.

Guest favorite

Guest suite in Brooklyn

4.93 out of 5 average rating, 173 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Guest favorite

Rental unit in Providence

4.96 out of 5 average rating, 472 reviews

Sunny, East Side apt!

Our one-bedroom apartment is plenty spacious for two people and a cozy stay for more than two. It's a stone's throw away from Hope Village, where there is plenty of charm, shopping, and great food. We are less than a mile from Brown and RISD. The apartment has its own private entrance. There is no parking on the premises, however, there is plenty of free street parking, very often right in front of the house.

Guest favorite