Holiday Rentals in Westerly, RI

499 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Westerly, RI holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

499 Holiday rentals and Airbnb in Westerly, RI

Best family friendly Westerly, RI holiday rentals

Among the 499 accommodations in Westerly, RI, here are the 4 best family friendly rentals

Historic Home, Walk To Seaport And Downtown - Westerly, RI
9.8 10 reviews

Historic Home, Walk To Seaport And Downtown

house, Stonington
This Stonington townhouse, near Williams Beach, is an eight-minute walk from Mystic Seaport and 2.6 kilometres from Olde Mistick Village.
The 188-square-metre property sleeps eleven guests in three bedrooms and two bathrooms, boasting a fully equipped kitchen, private balcony, garden, free Wi-Fi, and free parking.
Walk To Pawcatuck River: Family-friendly Home! - Westerly, RI
9.8 57 reviews

Walk To Pawcatuck River: Family-friendly Home!

house, Stonington
This charming house is located in Pawcatuck, a peaceful area just 8.5 miles from Mystic Seaport and 14 miles from Foxwoods Casinos. The property has received excellent user ratings for location, cleanliness, and overall experience.
The house is a spacious 3-bedroom property that can comfortably accommodate up to 4 guests. It features a well-equipped kitchen, a garden, a patio with river views, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Mystic Refuge W/ Patio < 1 Mi To Downtown! - Westerly, RI
No reviews

Mystic Refuge W/ Patio < 1 Mi To Downtown!

house, Stonington
Book this Holiday rental. This accommodation is based in Stonington.
Services and facilities include air conditioning, a washing machine and a kitchen.
Stonington Borough  2 Bed, 2 Bath, Sleeps 6, Close To Beach, Fire Place, Pets - Westerly, RI
10 77 reviews

Stonington Borough 2 Bed, 2 Bath, Sleeps 6, Close To Beach, Fire Place, Pets

apartment, Stonington
This charming Stonington Borough apartment is situated just a short distance from the bustling town of Mystic, offering easy access to its attractions, including Mystic Seaport and the Mystic Aquarium. The apartment has received excellent ratings from previous guests, highlighting its comfortable and convenient nature.
The apartment is a spacious two-bedroom, three-bathroom property that comfortably accommodates up to six guests. Amenities include a fully equipped kitchen, a private courtyard with a fire pit, a large deck with a dining area, and a karaoke station for entertainment, ensuring a memorable stay for the whole family.

Best Westerly, RI holiday rentals with a pool

Among the 499 accommodations in Westerly, RI, here are the 1 best rentals with a pool

Brand New Home Close To Charlestown/westerly Beaches. - Westerly, RI
9.8 46 reviews

Brand New Home Close To Charlestown/westerly Beaches.

apartment, Westerly
This Bradford holiday home is located 4km from Burlingame State Park and within 10km of Captain Bruce Ladd Memorial Dog Park and Wilcox Park in Westerly, Rhode Island.
This three-bedroom, two-bathroom property sleeps eight guests and boasts a private pool, fully equipped kitchen with dishwasher, smart TV, patio, barbecue, and washing machine; nearby attractions include hiking trails and dog parks.

Frequently asked questions about holiday rentals in Westerly, RI

  • What should a first-time visitor not miss in Westerly, RI?

    Westerly is full of charm! You shouldn't miss the historic Watch Hill Lighthouse, a beautiful landmark with stunning views. Also, take a stroll along the Westerly Town Beach, a lovely sandy beach perfect for a relaxing day.
  • What are the best Airbnb and holiday rentals in Westerly, RI?

  • Which neighborhood in Westerly, RI should you consider for a vacation rental?

    For a classic seaside experience, consider Watch Hill. It's a charming area with beautiful houses and a lively atmosphere. If you prefer a more relaxed vibe, try the quieter neighbourhood of Misquamicut, known for its long sandy beach.
  • What are the most popular Airbnbs in Westerly, RI?

  • What are the top family-friendly attractions in Westerly, RI?

    The Mystic Aquarium in nearby Mystic, Connecticut, is always a hit with families. In Westerly itself, the Wilcox Park is great for kids, with a playground, a carousel, and a pond. And don't forget the Westerly Town Beach for some fun in the sun!
  • What are the best holiday rentals with a pool in Westerly, RI?

  • When is the best time to book a vacation rental in Westerly, RI?

    The summer months, from June to August, are the busiest, so booking in advance is essential. If you prefer a quieter experience and milder weather, consider visiting in the shoulder seasons, spring or autumn.
  • What are the best rentals for families and kids in Westerly, RI?

  • What events or festivals should visitors check out in and around Westerly, RI?

    The Watch Hill Beach Party in July is a lively event with music, food, and fireworks. In August, the Westerly Art & Craft Fair is a great opportunity to browse local art and crafts. If you're around in September, check out the annual Westerly Wine & Food Festival.
  • What are the best rentals or Airbnbs with a jacuzzi in Westerly, RI?

  • What are the best budget-friendly activities in Westerly, RI?

    Take a walk or bike ride along the scenic Westerly Bike Path, which runs along the Pawcatuck River. You can also enjoy a picnic at Wilcox Park, or explore the charming shops and galleries in downtown Westerly.
  • What are the best restaurants with local dishes in Westerly, RI?

    For fresh seafood, try The Cooked Goose in Watch Hill. If you're looking for a classic New England dining experience, head to The Windjammer in Misquamicut, known for its lobster rolls and clam chowder.
  • What are the best walking or cycling routes in Westerly, RI?

    The Westerly Bike Path is a great option for a leisurely bike ride or walk, offering scenic views of the Pawcatuck River. For a more challenging ride, try the Watch Hill Loop, which takes you through the charming streets of Watch Hill and offers stunning ocean views.
  • Are there pet-friendly attractions in Westerly, RI?

    Yes, many places in Westerly welcome furry friends. Westerly Town Beach allows dogs on a leash during certain hours, and Wilcox Park has a designated dog park. Many restaurants also have outdoor seating that's pet-friendly.
  • What are the benefits of choosing a vacation rental in Westerly, RI?

    Vacation rentals offer more space and privacy compared to hotels. They can also be more budget-friendly, especially for families or groups. Many rentals are located in desirable areas, offering easy access to local attractions and amenities.
  • What are the top sports attractions and facilities in Westerly, RI?

    Westerly has a few sports facilities, including the Westerly Recreation Center, which offers a variety of programs and activities. For outdoor sports, there are plenty of options, like the Westerly Town Beach for swimming and sunbathing, and the Pawcatuck River for kayaking and paddleboarding.

Popular destinations

Best Westerly, RI holiday rentals with a balcony

Mini Palace @ Mystic Seaport & Aquarium: 5 Queen Beds 1 Bunk Bed - Westerly, RI
9.6 196 reviews

Mini Palace @ Mystic Seaport & Aquarium: 5 Queen Beds 1 Bunk Bed

apartment, Stonington
This modern split-level house is located just a block from the Mystic River and a short walk to Mystic Seaport Museum, offering easy access to the area's attractions. The property consistently receives excellent ratings for location, cleanliness, and overall experience.
The spacious house, spanning 204 square metres, comfortably accommodates 12 guests in its four bedrooms and two bathrooms. The property boasts a range of amenities including a fully equipped kitchen, a furnished outdoor deck, high-speed internet, and a spa, making it ideal for families and groups seeking a comfortable and enjoyable stay.
Mystic Refuge W/ Patio < 1 Mi To Downtown! - Westerly, RI
9.7 88 reviews

Mystic Refuge W/ Patio < 1 Mi To Downtown!

house, Stonington
This Stonington apartment is conveniently located less than a mile from downtown Mystic, a charming New England town, and a short 4-minute walk from the renowned Mystic Seaport museum. This apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment offers 84 square metres of space, accommodating up to 6 guests in its two bedrooms and one bathroom. It's well-equipped with a kitchen, air conditioning, a private patio, and free Wi-Fi, making it ideal for a comfortable and enjoyable stay.
Historic Home, Walk To Seaport & Downtown - Westerly, RI
10 31 reviews

Historic Home, Walk To Seaport & Downtown

house, Stonington
The Avery Suite, a historic townhouse in Mystic's downtown area, is located steps from the Mystic Drawbridge and a short walk (approximately 0.8 km) from Mystic Seaport and Mystic Pizza.
This three-bedroom, two-bathroom property offers 188 square metres of space, sleeping up to six guests, and features a chef's kitchen, smart TVs, high-speed Wi-Fi, and a private patio; ample on-site parking is available for three cars.
The Sea Shanty Suite · Walk Mystic-train/ev Lvl-2 - Westerly, RI
No reviews

The Sea Shanty Suite · Walk Mystic-train/ev Lvl-2

apartment, Stonington
This updated one-bedroom flat in Mystic offers convenient access to Stonington, being a 10-minute walk to historic downtown and a 15-minute walk to the Mystic Amtrak station.
This 60 square meter apartment accommodates up to four guests and features a newly updated kitchen with granite countertops and a dishwasher, in-unit laundry, a shared Level-2 EV charger, and outdoor Adirondack chairs, all a short drive from Mystic Aquarium, Mystic Seaport, and Foxwoods Resort Casino.

Best Westerly, RI holiday rentals with parking

Walk To Downtown Westerly | Near Beaches | 4br 3ba - Westerly, RI
10 46 reviews

Walk To Downtown Westerly | Near Beaches | 4br 3ba

apartment, Westerly
This Westerly apartment, a brand new 2025 listing, is situated in the historic Italian North End, within walking distance of Westerly's Amtrak station and the Grey Sail Tap Room, and a short stroll from downtown shops and restaurants.
The four-bedroom, three-bathroom dwelling sleeps eight guests, boasts a fully equipped kitchen, private patio with grill (seasonal), and includes bedding, towels, and beach chairs; individual air conditioning units are provided in each room.
Beach Escape. Walk To Beautiful Beaches - Westerly, RI
9.9 160 reviews

Beach Escape. Walk To Beautiful Beaches

apartment, Westerly
This two-bedroom apartment is located just 0.8km from the beach in Westerly, making it perfect for a seaside getaway. The apartment has received excellent ratings for its cleanliness, location and overall experience.
The apartment has a spacious open plan layout and can accommodate up to three guests. You'll find everything you need for a comfortable stay, including a fully equipped kitchen, two bathrooms, air conditioning, a garden and parking.
Hidden Haven - Westerly, RI
9.9 249 reviews

Hidden Haven

house, Stonington
This charming guest house is situated in a tranquil setting just a short distance from Stonington Borough, with Mystic, Westerly, and Rhode Island beaches all within easy reach. The property has received consistently excellent ratings for its location, cleanliness, and overall experience.
This cosy cottage offers one bedroom and one bathroom, comfortably accommodating up to four guests. It comes equipped with a fully-functional kitchen featuring a fridge, microwave oven, and dishwasher, as well as air conditioning and parking.
Downtown Westerly Getaway Near Beaches & Mystic! - Westerly, RI
10 6 reviews

Downtown Westerly Getaway Near Beaches & Mystic!

apartment, Westerly
This Westerly holiday home is conveniently located near Westerly Train Station (a 10-minute walk), Wilcox Park, and Westerly Public Library.
The two-bedroom apartment, sleeping six, offers a fully equipped kitchen, in-unit laundry, free Wi-Fi, a billiard table, and on-site covered parking.
©2026 cozycozy.com