
Holiday houses in Westerly
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Top-rated holiday rentals in Westerly
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Heathers On High Street King Bed/Twin Bed
Experience Westerly life like a Local! Enjoy this centrally-located Apartment close to Downtown. Easy highway access to the Beach and Casinos. Free Parking with Private entrance opens to a courtyard with Gazebo Sitting area and a Grill just for you! The 2 Bedroom Apartment is located on the 2nd floor with a Full Kitchen/Living Room combination, 1 Bathroom, Washer/Dryer and Central Air. The Master Bedroom has 1 King Bed with a new Nectar Mattress. Second smaller bedroom has a Twin Pillowtop Bed

Cheerful Cozy Colonial
Relax at this warm, welcoming, peaceful place to stay, with hiking trails nearby and only a 10-15 minute drive to various beaches, and a 10-minute drive to downtown Westerly. Set on 2+ acres, rejuvenate and connect with friends and family around the outdoor fire pit. Inside you will find a comfortable space with a full kitchen, living room, dining room, three bedrooms, and a full and half bath. Between Memorial Day and Labor Day, enjoy the outdoor shower after a long hike or trip to the beach.

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!

Downtown Oasis-1 bedroom-Walk to it all-sleeps 4
Downtown 1 bd, 1 bth unit. Park your car & walk downtown to shop, grab a bite, catch a movie at the United Theater or take a stroll in beautiful Wilcox park. This gem is in the heart of Westerly and only a 10min. drive to the beach. Finish your day on the back porch overlooking the fenced in yard. Can sleep 4. 1 bdrm with Queen bed. The living room has a pullout couch that turns into full size bed. Grocery, restaurants, laundromat are all steps away from this well kept secret on a dead end Rd

Brand New Private House in a Charming Beach Town
Stunning new house in a quiet neighborhood! 10 minutes to beaches! Enjoy this 3 bedroom home all to yourself with a spacious kitchen, grill & patio. Centrally-located and just a few minutes from historic downtown Westerly, less than 20 minutes from Mystic attractions (aquarium, seaport museum, village) and the Foxwoods Resort and Casino and outlets. Great backyard, toys, books for kids! Fireplace! Washer, dryer, and dishwasher for convenience. Public basketball and tennis courts across st.

Morgan Suite - spacious | hot tub | water views!
The Morgan Suite is a private Airbnb located in a quiet neighborhood along the Pawcatuck River. Just minutes to downtown Westerly, downtown Mystic, beaches, breweries, wineries, shops, restaurants and much more. This Airbnb a perfect for a romantic getaway or a relaxing memorable vacation with a friend. If you are looking to explore a new area and relax, the Morgan Suite is for you! The home is spacious, newly renovated with excellent amenities. Newly added - hot tub and massage chair!

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

Waterfront in the Heart of Watch Hill
Wake up, step onto your balcony and stare out across 3 states at the same time. With vaulted ceilings, 2 separate decks and bay windows that really DO look out over the bay, this property is truly unique. The ideal home away from home, this unit couldn’t be more centrally located. Swim, shop, enjoy a nice dinner, then retire to the third floor balcony to watch sunsets that defy description. However long your stay, this space is a great reminder of the unique gem that is Watch Hill.

the single fin
Welcome to our home in Westerly. We are nestled in a bustling downtown in close proximity to RI's beautiful coastline. Our tight knit community is drawn to the ocean and interconnected through everything within. Become a local if even for just a weekend. Walk downtown on Elm St and through Wilcox Park in route for a well crafted meal, live music, or to browse our shops. Whether packing a surfboard, fishing rod, or a good read, make sure you've got plenty sun screen and an appetite.

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.

Vibrant 2 Bedroom Apt - Conveniently Located
Experience premier downtown living in Westerly! Our stylish apartment offers unbeatable convenience, just steps from downtown attractions. With the Amtrak station less than a mile away, travel is a breeze. Enjoy sandy beaches just 4 miles away and easy access to Westerly Hospital, less than a mile. Perfect for jet-setting professionals seeking the ultimate blend of work and play in Westerly's vibrant heart! Any questions or requests to book direct please contact me.

Ocean Shire Coastal Cottage + Beach Pass
Welcome to this modern spotless beach cottage, 5 mins from amazing Watch Hill and Misquamicut beaches. Beach pass included. Kids most welcome. 🏖️ Watch Hill/Beaches: 5 mins ⚓ Historic Mystic: 18 mins 🏰 Newport: 50 mins ✈️ Block Island flight : 5 mins Cottage on 1.4 acres total privacy surrounded by trees with lavish gardens to enjoy morning coffee. Easy access to downtown, stores, restaurants, and wineries. Water sports and beach life at your doorstep.
Popular amenities for Westerly holiday rentals
Other great holiday rentals in Westerly

Westerly Suite: Explore Mystic and Beaches - Pets

Bird's Eye View Waterfront Unit

Comfortable Clean 3-Room Private Suite Westerly RI

Walk to Downtown Westerly | Near Beaches | 4BR 3BA

Central to Westerly Beaches and Mystic

Misquamicut Groove Beach Cottage

Beach Town New Home

Cozy New England Bungalow
When is the best time to visit Westerly?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $389 AUD | $362 AUD | $354 AUD | $325 AUD | $363 AUD | $443 AUD | $515 AUD | $506 AUD | $408 AUD | $389 AUD | $359 AUD | $320 AUD |
| Avg. temp | -2°C | -1°C | 3°C | 8°C | 13°C | 18°C | 21°C | 21°C | 17°C | 11°C | 6°C | 1°C |
Frequently Asked Questions
What are the best places to stay in Westerly?
Many travelers stay near Watch Hill for shoreline access and boutiques or around Misquamicut for a classic beach atmosphere. Downtown neighborhoods appeal to those who enjoy walkable streets, dining, and the town’s historic center.
What are the best things to do in Westerly with kids?
Kids frequently enjoy the Flying Horse Carousel in Watch Hill, tidepooling or sandcastle-building at Misquamicut Beach, and nature walks around Wilcox Park. Local spots throughout Westerly have family-friendly eateries and ice cream shops.
What are some of the best things to do in Westerly?
Explore the historic streets of Watch Hill, relax on Misquamicut Beach, and wander the gardens of Wilcox Park. The town also has art galleries, seasonal farmers markets, and locally owned restaurants.
How is the weather in Westerly?
Westerly has cold winters around 19–43°F (-7–6°C) and warm summers near 60–80°F (16–27°C). Light jackets and layers are helpful in spring and fall—rain is common year-round, with slightly sunnier, drier days in summer.
When is the best time to visit Westerly?
Late spring through early autumn is often recommended for beaches, outdoor events, and mild weather between 54–80°F (12–27°C). Winter appeals to those who prefer a quiet coastal experience and holiday festivities.
What are the best places to visit in Westerly?
Explore Watch Hill for coastal views and historic charm, stroll through Wilcox Park for gardens and green space, and visit the Ocean House for architectural interest. The area also has beaches, art spaces, and local shops that often draw travelers.
What are some hiking trails in Westerly?
Hikers often explore the trails at Dr. John Champlin Glacier Park and the Woody Hill Management Area. Both locations are known for woodland paths and quiet nature walks.
What are some family activities we can do in Westerly?
Families often explore Misquamicut Beach, enjoy the vintage Flying Horse Carousel in Watch Hill, and picnic in Wilcox Park. Mini golf, ice cream shops, and local nature centers add options for all ages.
What are some of the best day trip ideas from Westerly?
You can explore historic villages, guided lighthouse tours, and nature preserves in the surrounding region. Vineyard visits, local art galleries, and small coastal towns nearby are often suggested for a unique local experience.
Are there any pet friendly accommodations available in Westerly?
Westerly has pet-friendly accommodations, particularly near the beach and in the downtown area. Many local parks and some outdoor dining spots welcome dogs, but it is a good idea to confirm amenities and guidelines with each host.
What are some local tips for visiting Westerly?
Locals suggest arriving early on beach days, checking out independent coffee shops around downtown, and exploring quieter coastal spots beyond the main beach areas. Packing layers and comfortable shoes helps, as weather can shift, especially near the water.
What is Westerly known for?
Westerly is known for its sandy beaches, historic Watch Hill area, and a lively arts community. Many also explore its Victorian-era architecture, family-owned eateries, and small-town charm along the coast.
What are the best hidden gems to explore in Westerly?
Explore the quieter shoreline at Napatree Point Conservation Area, local art spaces, or secluded trails in the Woody Hill Management Area. Off the main routes, you may find independent bookstores and bakeries tucked into side streets.
What are the best foods to try in Westerly?
Clam cakes, stuffies (stuffed quahogs), and freshly caught seafood are frequently suggested, along with Italian-American specialties reflecting the area’s heritage. Local ice cream shops and bakeries are favorites for dessert.
What should I bring for a trip to Westerly?
Pack sun protection, a hat, and swimwear for beach visits, along with a light rain jacket and comfortable walking shoes for exploring town or parks. A sweater or layer is useful for cool evenings near the water.
What is the nightlife in Westerly like?
Westerly’s nightlife is centered around local pubs, relaxed wine bars, and venues with live music. Around downtown and near the beach, you’ll find casual spots for cocktails, beer, and late-night bites.
What are the most popular events or festivals in Westerly?
Westerly has outdoor concerts in Wilcox Park during summer, arts festivals, and annual celebrations around Watch Hill and Misquamicut Beach. Seasonal farmers markets and local heritage events are also frequently suggested.
Are there family friendly vacation rentals in Westerly?
Westerly has a range of family-friendly vacation rentals, especially near beaches and in quieter neighborhoods. Many options feature kitchens, yards, or easy access to parks and local attractions.
Quick stats about holiday rentals in Westerly

Total holiday rentals
Explore 320 holiday rentals in Westerly

Nightly prices starting at
Westerly holiday rentals start at $43 AUD per night before taxes and fees

Verified guest reviews
Over 13,930 verified reviews to help you choose

Family-friendly holiday rentals
210 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 90 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
310 of Westerly holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Westerly rentals

4.9 Average rating
Westerly stays are highly rated by guests—averaging 4.9 out of 5!
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- Brown University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- East Matunuck State Beach
- Charlestown Beach
- Ocean Beach Park
- Bonnet Shores Beach
- Southampton Beach
- Mystic Seaport Museum
- Easton Beach
- Mystic Aquarium
- Roger Williams Park Zoo
- Point Judith Lighthouse
- Narragansett Town Beach
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- The Breakers
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