Family-friendly vacation rentals in Watch Hill, Westerly

Find and book unique family-friendly homes on Airbnb

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

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Mystic

4.98 out of 5 average rating, 208 reviews

Mystic Cottage Retreat, near downtown

This recently renovated cottage is at the top of a quiet lane with a sweeping meadow view. Single level. Two bedrooms sleep four (queen and two twin beds); new, well-equipped kitchen and one bath, open living area, deck and patio. Light and spacious. Working fireplace, central A/C; W/D; expanded cable TV and wifi; off street parking for two cars. Market/deli nearby; pleasing walk (less than a mile from center of Mystic)- restaurants, shops, marinas, etc. Near Amtrak station. Great retreat!

Nov 30 – Dec 7

G$46,027 GYD per night

Guest favorite

Guesthouse in Charlestown

4.88 out of 5 average rating, 269 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.

Feb 19 – 26

G$20,177 GYD per night

Guest favorite

Home in Stonington

4.95 out of 5 average rating, 166 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.

Dec 12 – 19

G$45,344 GYD per night

Guest favorite

Home in Stonington

4.97 out of 5 average rating, 185 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.

Mar 2 – 9

G$107,940 GYD per night

Guest favorite

Farm stay in Hopkinton

4.98 out of 5 average rating, 192 reviews

Farm with a few goats on a lake close to beaches.

This is a bright walk out apartment in our home with a private entrance. We will be here but we give you all the privacy that you want. I have recently lost 3 goats. I still have two goats. This is a rural town 7 miles from Westerly, Rhode Island, and about 12 miles from Mystic. Please read the whole description of this property to make sure it is suitable for your family. Please read my reviews. I think my guests describe the accommodation even better than I do!

Apr 24 – May 1

G$33,434 GYD per night

Guest favorite

Guest suite in Westerly

4.96 out of 5 average rating, 120 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.

Feb 1 – 8

G$53,843 GYD per night

Guest favorite

Cottage in Charlestown

4.88 out of 5 average rating, 132 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.

Dec 28 – Jan 4

G$146,710 GYD per night

Guest favorite

Guest suite in Brooklyn

4.92 out of 5 average rating, 153 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.

Sep 8 – 15

G$15,398 GYD per night

Guest favorite

Guest suite in South Kingstown

4.94 out of 5 average rating, 116 reviews

Guest suite on private lake

Scenic lake-front guest suite and access to 2 kayaks. Lake is ideal for swimming, fishing and paddle boarding. Five minutes to the Amtrak station, thirty to Newport, RI and fifteen to RI's best beaches. If you are interested in touring New England, the location is ideal for day trips to Martha's Vineyard, Boston, and NYC. Property sits in the shadow of URI. The suite sleeps up to 2 comfortably, with a queen-sized bed.

Aug 17 – 24

G$30,326 GYD per night

Guest favorite

Tiny home in Newport

4.95 out of 5 average rating, 265 reviews

"ROOM AT BOB'S'

WINTER MONTHLY RENTAL: DECEMBER 1, 2023 - APRIL 30, 2024 2 NIGHT MIN AVAILABILITY: MAY 5 - NOVEMBER 30, 2024 At "Room at Bob's" guests enjoy the entire apartment. Full kitchen with a small fridge and stove. A nice sitting area to watch a movie, if you are not out and about in town. The bedroom has a comfortable queen sized bed and a small closest. The bathroom has a stand up shower and with all the amenities.

Nov 4 – 11

G$35,769 GYD per night

Guest favorite

Apartment in Providence

4.95 out of 5 average rating, 443 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.

Oct 7 – 14

G$16,412 GYD per night

Guest favorite

Home in Montauk

4.91 out of 5 average rating, 418 reviews

DITCH PLAINS SURF HOUSE

Beach house on quiet street, 200 yards to Montauk's best surfing beach, Ditch Plains. The house is a simple all white home with 2 decks, BBQ, bikes, kayak, and easy open floorplan. You can hear the ocean all day long on this hidden Montauk street. Easily walk or bike to the beach, where you find waves, food trucks in the summer & miles of sand and ocean heading west to Montauk.

Dec 1 – 8

G$46,767 GYD per night