Discover a selection of 500 vacation rentals in Westerly, RI that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $134 per night, and houses and cottages are popular options for a stay in Westerly. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Westerly
Destination guide

A gem of a spot in tranquil Rhode Island

Westerly may not be a Rhode Island big gun, but what it lacks in global recognition it makes up for with its picture-perfect town center, Victorian-era central park, and Atlantic views. A popular summer getaway, a trip here is often associated with time spent on soft-sand beaches, enjoying lazy days with friends and family. There’s more to Westerly than beaches, though. The town offers an array of boutique shopping and tempting dining options, particularly in affluent Watch Hill. Westerly vacation rentals range from historic New England cottages to modern waterfront condos, so finding a place to call your own has never been so easy.

Things to do

Festival fun and cultural appeal in Westerly

Westerly knows how to throw a party and this is best experienced at one of the town’s regular festivals. Both spring and fall festivals, as well as an annual Shakespeare Festival and the Summer Pops, draw in crowds of up to 20,000. Join locals and out-of-towners to enjoy local works of art, live entertainment, and family-friendly attractions such as petting zoos and Ferris wheels. Elsewhere, you can inject a little culture into your stay by heading to Napatree Point, the site of an old Navy post by the name of Fort Mansfield, or make a splash at the seasonal Water Wizz of Westerly, with its “super speed” slides.


Taking it easy in Westerly

Take life at your own pace in Westerly. The 3-mile Misquamicut Beach provides the perfect backdrop for kayaking and paddle boarding, while charismatic captains at shoreline marinas invite you to venture further into the water on a variety of year-round boat trips and cruises. When it’s time for a change of scenery, the plentiful shops and restaurants in the town’s hip downtown area are complemented by the chance to wander through the town’s 14-acre Victorian-era Wilcox Park. Events at the Colonial and Granite Theatres will help you round off your evening before returning to your Westerly vacation rental.


An ever-changing landscape in Westerly

New England’s ever-changing landscape gives Westerly year-round appeal. Admittedly, the winters can be frosty, but the town’s boutique stores and array of dining options will provide an enticing escape from the cold. Spring offers warmer days and the first signs of the region’s flowers, while summer is the perfect time to enjoy the Atlantic beaches, with temperatures from June through September often surpassing 70. It is fall, however, that often attracts the most travelers. The blazing colors, combined with more comfortable temperatures, make October a great time to visit Westerly and indeed anywhere in New England.

Natural features

Exploring the beaches and other natural features in Westerly

Whether you're an adventurous traveler or just want to take in the scenery, Westerly is a great place to spend some time outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Misquamicut State Beach (3.9 mi / 6.4 km)
  • East Beach Watch Hill (5 mi / 8 km)
  • East Beach (8.5 mi / 13.8 km)
  • Charlestown Town Beach (9.9 mi / 16 km)
  • Matunuck Beach (14.3 mi / 23 km)
  • Ocean Beach Park (14.9 mi / 24 km)
How to get there

How to get to and around Westerly

The nearest airport is in T.F. Green Airport (PVD), located 31.4 mi (50.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Westerly, RI (WST-Westerly State), which is 2.2 mi (3.5 km) away.

If you'd prefer to travel by train, the main station serving the city is Westerly Station.

What are the top vacation rentals in or near Westerly?

Whether you're searching for a cozy retreat for you and your special someone or someplace roomy to fit friends and family, you'll find some top vacation rentals in and around Westerly. Here are a couple to get you thinking:

  • "Lovely 3 Bedroom 3 Bath Across From The Beach" is a popular choice. Around 17 miles from Westerly, it has 3 bedrooms and lots of useful amenities, including outdoor furniture and an ocean view.
  • Another top choice is "Secluded Waterfront Location With Dock", which is around 4 miles from Westerly. Featuring 4 bedrooms, a dishwasher and internet services, it has everything you need to keep you comfortable and happy.

For even more great options, use the search bar at the top of the page to find the perfect Westerly vacation rental for you.

Can I find log cabins to rent in or near Westerly?

You bet! From rustic retreats to luxury escapes, we've got a wide range of log cabins to rent in or around Westerly. If you're into adventure, check out:

  • "Log Cabin - Glam Camping": This awesome escape is the perfect base if you're an outdoorsy type. Cycling and fishing are two activities you can do in the area when you're not chilling in your cozy cabin.
  • "Cabin By The Sea - Newly Renovated Log Cabin Near The Beach": Stay in and enjoy the relaxed vibe or experience some of the fun activities nearby, such as fishing and horse riding. Chill or active, the choice is yours.

What are the top-rated vacation rentals for weekend getaways in or near Westerly?

Nothing tops a short escape to blow away the cobwebs. Pack your overnight bag and catch your breath at one of these enticing weekend getaways in and around Westerly:

  • "Gorgeous Contemporary. . . Stunning Space Indoors And Out" is a popular option around 20 miles northeast of central Westerly. You'll never have to wander far to find something to keep you busy around this escape. Get out and discover Vineyard Fast Ferry and Fort Wetherill State Park. Activities like windsurfing and hiking and biking will add the finishing touch to your mini break.
  • "Misquamicut Westerly Secluded Beach Cottage 2018 Remodeled And Upgraded" is another great property where you can escape the everyday. Around 1 mile southeast of Westerly, use it as a base to enjoy some fishing or windsurfing. Clay Head Preserve and Scarborough Beach should also be on your must-do list while you're here.

Can I find studio apartments for rent in and around Westerly?

Studio apartments are hard to beat when it comes to convenience, location and affordability. Stay in one of these studio apartments for rent in or near Westerly and immerse yourself in the local culture:

  • Make "Big Style In Tiny House - 2 Miles To The Beach" your temporary home. This fantastic vacation rental comes with amenities including towels and a washing machine.
  • Alternatively, spend your escape at "Downtown Penthouse Apartment", which offers conveniences such as cable/satellite TV services and free WiFi.

With the moolah you save on your studio apartment, you can afford to discover even more of Westerly. Cultural attractions like The Contemporary Theater Company and Tomaquag Museum will help you get a better feel for the character of this destination.

Can I find short term rentals in or near Westerly?

Short-term rentals are plentiful in and around Westerly. Stay for a night or two in a luxury cabin, a budget apartment or a large home. Whatever sort of vacation rental you're searching for, you'll have plenty to select from with Vrbo. Here are some of our favorite options:

  • "Cozy Westerly Cottage" is close to the center of Westerly, so you'll have plenty of things to keep you busy. Make your way to cool attractions like Block Island Ferry and East Matunuck State Beach when you're not hanging out in your cozy digs.
  • "Big Style In Tiny House - 2 Miles To The Beach" is another excellent option. Consider adding Charlestown Town Beach and Carpenter's Grist Mill to your must-do list when it's time to sightsee.

What are the best romantic weekend getaways in or near Westerly?

Forget roses and chocolates. Sometimes all you need is to get away for the weekend, just you and your beloved. At Vrbo, we've got romantic getaways in and around Westerly that would make Cupid envious. Here are some we think you'll be enamored with:

  • Sneak off on Friday for a couple of passion-filled nights at "Lovely 3 Bedroom 3 Bath Across From The Beach". Approximately 17 miles from Westerly, this place comes with plenty of nice touches, including a nearby bay and winery tours.
  • "Secluded Waterfront Location With Dock" is another wonderful option that's guaranteed to impress. It's about 4 miles from Westerly and comes with a nearby bay and winery tours.

Are there mansions for rent in or near Westerly?

If you're after somewhere to reconnect with loved ones this vacation, you're going to need somewhere spacious. These mansions for rent in or near Westerly will fit your entire crew while doing it in serious style:

  • Located about 16 miles to the southeast of Westerly, "Walk To Mansion Beach" is the ideal place to relax and unwind in luxury. Amenities here include a nearby beach and a restaurant dining guide.
  • With a fireplace, a nearby beach and lots of other high-end amenities, "Mansion Beach Area, A/c, With D" will get your team's tick of approval. This sleek retreat is roughly 16 miles to the southeast of Westerly.

What are the best large group vacation rentals in or near Westerly?

Cast your eye over these large group vacation rentals in or near Westerly where you won't have to leave anyone off your invite list:

  • There's plenty of room to move at "Gorgeous Contemporary. . . Stunning Space Indoors And Out". Around 20 miles northeast of Westerly, this grand property has 4 bedrooms that sleep up to 12 guests. Amenities include a swimming pool and a kitchen.
  • Invite up to 12 of your best friends to "Westerly Beach House With Spectacular Views" and fill its spaces with laughter and love. This top option has 6 bedrooms and is around 1 mile to the south of central Westerly. It's crammed with features to keep large groups comfortable and content, including an ocean view and a kitchen.

What are the best houses for rent with a pool in or near Westerly?

Of all the amenities a vacation rental can have, a pool promises the most fun. Take a peek at these houses for rent with a pool in or near Westerly and spend your days splashing about. Just remember to take your inflatable swan:

  • Treat the gang to an unforgettable stay at "Big Style In Tiny House - 2 Miles To The Beach". There's a lot to love about this retreat besides its pool, such as a microwave oven and childrens activities.
  • Alternatively, unpack your bags at "Westerly Beach House With Spectacular Views". Along with a refreshing pool, you'll also have use of a garden and on-site watersports.

Westerly has an oceanic climate, with average summertime temperatures ranging between 65 ºF and 75 ºF. But you don't have to wait until summer to visit. Check out the search bar at the top of the page and adjust the filters to find the perfect Westerly vacation rental and organize your getaway for whenever you like.

What are the best large family vacation rentals in or near Westerly?

Every get-together with the family should be memorable. Whether you're organizing some time off with the kids or a party with relatives, our large family vacation rentals in or near Westerly offer a comfy home away from home with plenty of space for everyone:

  • About 17 miles to the east of Westerly, "Looking For A Vacation Home That Allows You To Walk To The Beach" has 3 bedrooms and fits up to 8 guests. It comes with a host of amenities, including a dishwasher and a theme park.
  • "Secluded Waterfront Location With Dock" also has the space you need to reconnect with loved ones. This option is around 4 miles to the southwest of central Westerly and accommodates 10 guests in its 4 bedrooms. A balcony and a microwave oven will help keep everyone content and comfortable.

If you're hoping to visit some family-friendly attractions in the area, you won't have far to go. The Flying Horse Carousel, Biomes Marine Biology Center and Water Wizz of Westerly offer fun for all the crew.