Vacation Home Rentals By Owner In Westerly, RI

Showing 20 Of 84 Vacation Rentals

$947.83

Waterfront in the heart of Watch Hill

Westerly, Rhode Island, United States

Wake up, step onto your balcony and stare out across 3 states at the same time. With its vaulted ceilings, 2 separate decks and bay windows that really DO look out over the bay, this property is truly one of a kind. 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 a sunset that defies explanation. Every night more brilliant than the one before. However long you’re with us, staying here will be a constant reminder of the true New England gem that is Watch Hill.

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$601.92

/ Nightly

Private Vacation Home

The Beach Cottage in Misquamicut - short walk to the beach!

Westerly, Rhode Island, United States

Charming beach cottage located in beautiful Westerly, RI. Perfect for couples, families and anyone looking for a coastal escape. The cottage offers three bedrooms, one full bathroom and is a short walk to the beaches and the Misquamicut strip.brbrIt has a well equipped kitchen with a stovetop, dishwasher and microwave. There is also a washer and dryer available for guest use. Outside, guests can utilize the outdoor grill and enjoy ample deck space with a dining table, Adirondacks, and loungers - covered by a retractable awning. brbrMinutes away from some of Westerly's best beaches in the coastal communities of Misquamicut, Weekapaug, and Watch Hill. Summer rentals come with a pass for Misquamicut Fire District Beach - a short walk from the cottage. brbrParking for two cars is available. brbrIf you are visiting Westerly outside of summer season the cottage offers a peaceful retreat. Although commonly sought after for its summer appeal, Westerly is just as lively and captivating in other seasons. Westerly is conveniently located off Interstate 95 and Route 1, allowing for easy exploration of neighboring seaside towns such as Mystic, CT and Matunuck, RI, and nearby casinos. brbrRENTAL AGREEMENT: Upon booking, a separate Host Rental Agreement will be provided via email. Execution of the agreement is required for stay and access.brbrSUMMER 2026:brWeekly bookings only, June 20th - September 5th. Saturday - Saturday. Exceptions made for monthly bookings.

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Bath

Sleeps

Exceptional(5)

$811.3

/ Nightly

Private Vacation Home

Westerly Retreat

Westerly, Rhode Island, United States

Fully equipped with everything you’ll need to enjoy your stay! Located near state parks and amazing beaches! With a short 15 minute drive you have access to fishing, kayaking, swimming, hiking, and restaurants. We are 20 minutes from Foxwoods Casino, and 35 from Mohegan Sun. Enjoy the nice patio overlooking a lush green backyard while having access to a grill, smoker, firepit, sectional couch and patio table set with an umbrella. This 4br 2b house is bright, immaculate, and updated throughout w/ AC in every room. brbrThe spacebr4 bedrooms:br1-Master with a king bed and a full bathroombr2-Queen bed br3- 2 single beds.br4- 2 twin beds with trundle, TV and toys. brbrFamily room with TVbrbrSitting area with TV and Electric Fireplacebrbr2 Full bathroomsbrbrEat-in Kitchen equipped with K-cups coffee maker, toaster, microwave, and water filterbrbrWasher and dryer

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Bath

Sleeps

Exceptional(18)

$682.37

/ Nightly

Private Vacation Home

5 STAR Coastal Farmhouse- Dog Friendly- 3BR in Westerly! Minutes to Beach & Town

Westerly, Rhode Island, United States

Get ready to relax in this delightful 3-bedroom home in stunning Westerly, RI. Seconds to Watch Hill, and all that downtown Westerly has to offer. Two bedrooms feature new cozy queen beds, and the primary, a new king that adjoins a full size bathroom. Enjoy the brand new farmhouse kitchen amenities, new appliances, butcher block counter tops, and a modern day home feel. Relax outside on the private outdoor deck, gaze at stars at night and watch the puddle jumpers take off for Block Island during the day. Perfectly situated at the end of a quaint culdesac street, this home is equipped for both long or short stays to make your home away from home or holiday as seamless as possible. Please note, guests do not have access to the garage, jet tub, and basement areas.

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$520.6

/ Nightly

Private Vacation Home

August or weekly rental bike to beach, walk to tennis!

Westerly, Rhode Island, United States

August or weekly rental until Labor Day! Our house is on a dead end street and 2 miles from the local beaches and a walk down the hill to Pond View Racquet & Paddle Club. A 3-bed home with two king beds, a bunk bed and a child’s bed, perfect for families. One full bath on the top floor, half bath on the main floor living area, and full bath on ground level with guest bedroom. A tv/playroom on the main floor. We also have an outdoor shower, full deck, and large backyard. There is an attached in law apartment if looking for more space for in-laws or a nanny. This would be at an additional cost. Please reach out with questions!

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Exceptional(4)

$1196.19

/ Nightly

Private Vacation Home

Waterfront Home with Private Dock

Westerly, Rhode Island, United States

Property located on Colonel Willie's Cove in town of Avondale, RI. Views of Napatree Point and Fishers Island. 1 Mile to downtown Watch Hill. Waterfront home with beautiful views and a boaters paradise.brbrPrivate cove with direct ocean access. Home situated on a quiet, dead end street. Dock will handle a boat up to 36 ft-3 ft draft (Mooring available for larger boats). 1200 sq ft deck. Screened porch. Outdoor Shower with changing room. Large back yard. Separate swim dock. House renovated in 2000. Open floor plan. brbrKeywords: House

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Exceptional(5)

$818.36

/ Nightly

Private Vacation Home

Large Winnapaug Pond Beach House

Westerly, Rhode Island, United States

This newly renovated home, wonderfully captures the essence of coastal living, inviting you to completely embrace the beach lifestyle for your vacation rental getaway. Don’t want to carry everything to the beach No problem, our home includes everything you need to enjoy to have a relaxing experience at the beach. Better still, take a leisurely walk or bike ride to Watch Hill Village. Bring your bikes or ask if we have . . Our quiet, tranquil, setting offers outdoor patio space also for your enjoyment whether it is a morning coffee or an evening cocktail as you hear and listen to the ocean, waves breaking loudly around the corner, as you whine down your day, or start your day! This beautiful beach house has air conditioning window units three bedrooms, full kitchen, dining, living area with an open concept. in addition, there is a large family room on the lower level where you can enjoy your downtime. The house sleeps comfortably eight and it’s beautifully furnished with every attention to detail so that you simply need to relax and enjoy your stay! drive, 1.5 hours from Boston, 2.5 hours from New York City, 30 minutes to Newport or mystic , 45 minutes to Providence. If you’re heading to the airport, it’s 35 minutes to TF Green and five minutes from Westerly airport. The Amtrak train station is right there in downtown westerly.

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Exceptional(15)

$721.05

/ Nightly

Private Vacation Home

Steps to a private beach, enjoy sunsets and kayaking from your backyard!

Westerly, Rhode Island, United States

This listing is for the entire home. 13 Breach Drive is a unique home which offers the best of both water worlds! Situated just seven houses from the gorgeous Atlantic Ocean and a private beach on a quiet street near the Weekapaug section of Westerly, Rhode Island. This home also offers a backyard access to the Weekapaug Breachway, a waterway leading to both the Winnapaug Pond and the out to the Atlantic Ocean. Just bring your canoe, kayak, paddle board and beach chairs to enjoy what the Weekapaug Breachway and Winnapaug Pond and the private beach have to offer.brbrThis two family home offers three bedrooms and two and one half baths and sleeps a total of 12. The upper level sleeps 4 and lower sleeps 8 comfortably. Spectacular sunrises and sunsets can be seen from three decks (two in the rear and one in the front).

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Exceptional(14)

$461.34

/ Nightly

Private Vacation Home

Lovely Westerley Home w/ Yard & Grill!

Westerly, Rhode Island, United States

Planning your next memorable escape Look no further than this spacious 3-bedroom, 2-bath vacation rental in Westerley! With its prime location, this home gives you convenient access to must-visit attractions like Fenway Beach and The Stonington Lighthouse Museum. After a day of exploration, relax on the patio while enjoying a delicious barbecue cooked on the gas grill. With ample space for everyone, this house is perfect for creating unforgettable memories with family and friends!brbr-- THE PROPERTY --brbrRE.04928-STR | Furnished Patio | Ping Pong Table | Free WiFi | 2,000 Sq FtbrbrBedroom 1: King Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: Queen BedbrbrHOME FEATURES: Smart TVs, dining table, ceiling fans brKITCHEN: Refrigerator, stove/oven, Keurig coffee maker, microwave, dishwasher, dishware & flatwarebrGENERAL: Washer & dryer, towels, linens, complimentary toiletries, central air conditioning/heatbrFAQ: Stairs required for access, 1 exterior security camera (facing entryway)brPARKING: Driveway (4 vehicles), free street parkingbrbr-- THE LOCATION --brbrSUN AND SAND: East Beach (6 miles), Fenway Beach (7 miles), Blue Shutters Beach (10 miles), Quonochontaug Beach (10 miles), East Matunuck State Beach (22 miles)brOUTDOOR ADVENTURES: Burlingame State Park (12 miles), Ninigret National Wildlife Refuge (12 miles), Trustom Pond National Wildlife Refuge (17 miles), RI DEM Division of Parks & Recreation (28 miles)brHISTORY BUFFS: Babcock-Smith House Museum (2 miles), The Stonington Lighthouse Museum (7 miles), Mystic Seaport Museum (10 miles), Point Judith Lighthouse (29 miles)brADRENALINE RUSH: Tree Trails Adventures Mystic (11 miles), Water Wanderers LLC (15 miles), Yale Outdoor Education Center (27 miles), Scenic Route - Wilber Ave (55 miles)brSEE THE SIGHTS: Stonington Point (7 miles), Westerly Town Beach (7 miles), Mystic Aquarium (9 miles), Block Island (44 miles)brAIRPORT: Rhode Island T.F. Green International Airport (37 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: Your safety matters. This property features 1 exterior security camera located on the back door, facing outward toward the entryway. It does not look into any interior spaces. The camera records video and sound continuously

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Exceptional(29)

$684.0

/ Nightly

Private Vacation Home

Relaxing Nestled btw Watch Hill & Weekapaug! BEACH, waterviews, newly renovated

Westerly, Rhode Island, United States

SUMMER 2026 CALENDAR OPENS JAN 5 ! Finest location-Nestled between Watch Hill and Weekapaug with Misquamicut attractions! Wonderful beach across the street, and salt pond with oyster farms behind house for excellent kayaking! Easy walk to Comforti Pavilion Swimming Beach (food, bathrooms, lifeguards, showers) use our beach cart! Or use our parking pass if you need to drive instead. Dusty's Dairy Bar, the WindJammer, mini golf, go carts, arcade, souvenirs- walk or bike to food, entertainment, shops! It's all right here! Everything else is just moments away by car, but who would want to leave Our house has just finished a major interior renovation. Quiet mini split ACs throughout! High Speed internet, streaming TV apps. Lower level play area with pool table and ping pong. You will love the views, nature, and memories at this house! We sure do! If you are arriving by AIR and not AUTO, check with Host regarding adding linens and towels which are not provided.

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Exceptional(47)

$1869.6

/ Nightly

Private Vacation Home

The Boulders - A Watch Hill Five Bedroom House

Westerly, Rhode Island, United States

Access all the beaches of Watch Hill while enjoying this property in the privacy of the historic Watch Hill Woods on 1.5 acres. Beautiful open lawn, mature trees and scenic backyard view with boulders and wildlife. Outdoor shower, small frog pond, Cedarworks play set and two-level deck. Upper deck with dining table and chairs, gas grill, a retractable awning and a small roofed living room space. Larger lower deck offers Adirondack bench and chairs, cast iron fire pit and covered additional outdoor couch and chairs. brbrHome was remodeled, including renovated kitchen and bathrooms, new carpets and floors. Home features cathedral ceilings, open living dining space, two working wood fireplaces, new Smart TVs, central A/C and Sonos sound system. brbrUpper level is a full floor master suite with high ceilings, living room area/office space with TV and large master bath. brbrMain level encompasses kitchen, den, open dining and living space with cathedral ceilings and windows, two bedrooms, one full bath and one half bath. brbrLower level has two bedrooms, full bath and an additional living room with TV and wet bar. Whole house was refurnished with a coastal chic vibe. brbrTwo car garage, plus additional bonus game garage with ping pong table, hockey nets/sticks and Foosball table.brbrTwo minutes drive (or 10 minute walk) to Avondale Marinas for Ocean boating, 5 minutes drive to Watch Hill village shops restaurants, Napatree Point Beach access, East Beach and Ocean House and 10 minutes drive to Weekapaug Inn.

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$3617.63

/ Nightly

Private Vacation Home

5 Star Ocean House Hotel - Rental Villa. Winter Season

Westerly, Rhode Island, United States

Luxurious Watch Hill - Ocean House Resort Rental Villa - Winter season rental - Very spacious with 3 Master suites. Real estate brokers preferred and protected for this 6-7 month term. brbrImpeccable condition. Previously not made available for rent in 2020 season. You will be the first renter in 2020. brbrThis is an OCEAN HOUSE RESORT Summer Rental Villa! Just Listed for Winter Season. Luxurious and large, newly renovated house in Watch Hill Village, features a quiet location, luxury beds, private pond, huge yard, ocean views, and expansive decks for grilling and entertaining. Walk to Ocean House for dinner and entertainment throughout the winter. Beaches and shops steps away. brbrYou will find plenty of room for a multi-generational family gathering. Take advantage of all Watch Hill has to offer and still have plenty of privacy. Enjoy the solitude, abundant wildlife and pond views in addition to seasonal views of the ocean from the upper floors. br brKids can take the short hop via quiet streets to village/beaches - off the main busy roads. brbrExcellent WI FI coverage in entire mansion. Wired Ethernet available in work in numerous work at home areas.brbrFull Six Month term winter rental beginning Oct 15 2023. $10,00 per month winter rate.brbrDecorated and furnished by the nearby Ocean House Spa and Resort for maximum charm and guest comfort, there are up to 8 bedrooms all with their own bathrooms. This includes 3 private Master Suites (yes!) each with private porches.brbrA large new designer kitchen,, Wolf and Sub Zero appliances, 6 zones of geo-thermal heat/air conditioning, gas fireplace and beautiful finishes make indoors easy and comfortable. Outdoors you are surrounded by hydrangeas, vegetable gardens, 2 acres of land and plenty of parking and short walks to harbor, beaches, shops and restaurants.brbrThe complete renovation includes all new electricity, plumbing and septic systems as well as lightning protection, a new full house fire sprinkler system, digital alarm system, and custom Pella windows and doors. The copper dome and cedar roof systems have been carefully rebuilt with love and respect for the architectural history of Watch Hill. brbrHistoric centerpiece to Watch Hill history with New York Times mentions from turn of century. brbr Entire winter season only. October 15, 2023- May15, 2024.

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Exceptional(28)

$1434.39

/ Nightly

Private Vacation Home

Westerly Beach House with Spectacular Views

Westerly, Rhode Island, United States

Style and comfort, plenty of space, water views from every front-facing window! This vacation spot is located on a hill above the Atlantic Ocean. Stay in and enjoy the spectacular views or get out and experience some of the best beaches and shopping in New England. The 4800 square foot house has four bedrooms and three baths on the three main levels (and an additional 2-room connected suite with half bath below at ground level). Whether you are looking for the beach, boating, golf, tennis, nature, culture or just relaxing, this is the place to do it. Solar powered with battery back-up.brbrThe panoramic ocean and pond views from this spectacular property are guaranteed to take your breath away! This location will delight even the most discerning renter seeking awesome views of the ocean and Winnapaug Pond. This spacious architect-designed home offers impressive wood and stone work. Perfect for a large and/or multigenerational family or two families renting together, the upper and lower levels, each with two bedrooms and a kitchen, can be separated. The main level (first floor) has two bedrooms (one with a balcony with ocean views), a full bath, family room/library, gourmet chef’s kitchen (with large granite island, cherry cabinets, and high end appliances), and a formal dining room (with gas fireplace and a second water-facing balcony). Double sliders open onto a hardwood deck and into a private, beautifully landscaped back yard. A glass-enclosed solarium in front steps out onto a stone patio with more pond and seascapes. The second level (with a private entrance option), has a MBR/marble ensuite bathroom with a third ocean facing balcony, game room (with a pool table), living room with river rock fireplace, and the fourth ocean-view balcony, plus a dedicated theater/media room with a 4k UHD projector and multichannel sound, and a second fully-equipped kitchen. On the 3rd floor is an enormous MBR suite with large bathtub and separate shower and a raised sitting area offering a fabulous vista of the Westerly shoreline, Winnapaug Pond, Long Island, Block Island and the starry sky. The lower level (floor 0, at ground level) has a bonus suite with two openly connected rooms, each with a walkout to the outside; there is sleeping space here for 4 more. The entire property is professionally landscaped, and has parking for 12 vehicles. Ride your bike or drive to Westerly beaches. Outdoor shower available. Play golf and tennis within walking distance. It’s a short drive to historic Watch Hill shops, restaurants, and nature. Beach pass included. Convenient to all that Watch Hill, Westerly, Mystic (20 minutes), Newport (50 minutes), and Providence (55 minutes) have to offer. Easy train and car access from Boston and New York; and there is Amtrak service to Westerly.brbrCentral air conditioning on 2nd and 3rd floor with minisplits providing AC on the first floor and lower level. brbrClose to the CT border and an easy weekend getaway from NYCbrbrBED INFORMATION:brMBR 1 - kingbrMBR 2 - king and queen sofabedbrBR 3 - full, two twins (bunkbed)brBR 4 - Queen brbrLibrary on 1st floor - full sofabedbrbrExtra bedrooms on lower level :brBR 5 - full; communicating with BR 6 - 2 twins + 1 trundle twin

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Sleeps

Exceptional(20)

$398.54

/ Nightly

Private Vacation Home

Westerly Vacation Home: Town Beach Access

Westerly, Rhode Island, United States

Make this charming Westerly, Rhode Island vacation home you're next coastal getaway! The 2-bedroom, 2-bath vacation rental features everything you need for a memorable trip with family, including abundant community amenities like prime beach access, tennis courts, a pickleball court and more. Venture off to the beach for a relaxing day on the water, and later, whip up a tasty meal with the help of the gas grill on the patio. Enjoy an alfresco beverage by the fire pit to wrap up the evening!brbr-- THE PROPERTY --brbrRE.0204891-STR | Free WiFi | Family Friendly | Town Beach Access | Fire Pit (Wood Provided) & Gas GrillbrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Living Room: Full Sleeper Sofa, Full Futon | Additional Sleeping: Pack ‘n PlaybrbrTOWN AMENITIES: Westerly town beach & pond access, showers, volleyball court, pickleball court, playscape playground brOUTDOOR LIVING: Patio w/ fire pit (wood provided), outdoor seating, outdoor shower, close proximity to beachesbrINDOOR LIVING: Smart TVs, stereo, dining table w/ seating for 6, breakfast bar, fireplace (decorative), family friendly w/ high chair & Pack n’ Play brKITCHEN: Well-equipped w/ refrigerator, dishwasher, microwave, cooking basics & spices, organic coffee/tea, snacks, toaster, blender, dishware/flatwarebrGENERAL: Free WiFi, linens/towels, complimentary toiletries, central A/C, in-unit washer/dryer w/ detergent, keyless entry, iron/board, trash bags/paper towels, beach towels/chairs & umbrellabrFAQ: Single-story home, 2 steps to enter, daily parking pass for beaches provided, 1 motion-activated doorbell camera at front entrancebrPARKING: Driveway (3 vehicles), additional street parkingbrbr-- THE LOCATION --brbrBEACHES: East Beach (2 miles), Misquamicut State Beach (2 miles), Westerly Town Beach (3 miles), Dunes Park Beach (4 miles), Fenway Beach (4 miles), Blue Shutters Beach (8 miles), Charlestown Town Beach (13 miles), East Matunuck State Beach (18 miles), Scarborough State Beach (24 miles), Roger Wheeler State Beach (25 miles)brOUTDOOR ADVENTURE: Ninigret Park (9 miles), Ninigret National Wildlife Refuge (9 miles), Burlingame State Park (9 miles), Kettle Pond Visitor Center & Trails (10 miles), Trustom Pond National Wildlife Refuge (14 miles)brLOCAL ATTRACTIONS: Watch Hill Lighthouse (4 miles), Flying Horse Carousel (4 miles), Quonochontaug Breachway (8 miles), Mystic Aquarium (15 miles), Mystic Seaport (16 miles), Theatre By the Sea (16 miles), Port of Galilee (26 miles), Point Judith Lighthouse (26 miles), Block Island Ferry (26 miles), Newport, RI (38 miles)brAIRPORT: Rhode Island T.F. Green International Airport (39 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: While this is a single-story home, there are 2 steps to enterbr- NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed

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Exceptional(18)

$524.4

/ Nightly

Private Vacation Home

Perfect 3-bedroom family house in beautiful Westerly, Rhode Island!

Westerly, Rhode Island, United States

Your cozy getaway awaits in Westerly at this fabulous house!brbrThis home comfortably sleeps 8, with 3 bedrooms including 2 queen beds, 1 full bed, and 2 twin beds, this tranquil retreat is perfect for families or groups of friends. br(see information below if your party is larger than 8).brbrEnjoy the convenience of this newly renovated family house with large spaces for relaxing! brbrHouse includes a well appointed ktichen with new appliances (large & small), televisions, tons of family games, WiFi, washer & dryer, and mini-splits in each room for AC & heat! brbrAll linens are provided - sheets, pillows, comforters, blankets and towels!brbrThe 2 bathrooms feature showers for your comfort with the primary bedroom having its own en suite bath with a walk-in shower.brbrBook now and enjoy everything this house has to offer including a private yard and a large rear deck with gas grill. brThe house is on a septic system; please be mindful of what does down sink drains and toilet paper only in the toilets.brHouse is close to all beaches on Atlantic Avenue, local golf, fabulous restaurants and more! Downtown Westerly has so much to offer and Watch Hill is right around the corner. You will be short drive to Mystic CT and Stonington CT, along with Foxwoods Resort & Casino.brbrFollow us on social media as we often post about local and seasonal events.br(F acebook = Coastal Charm)brbrIf you have a group larger than 8, for an additional fee we can accommodate additional guests! Inquire within prior to booking! brbrWe can’t wait to host you at Coastal Charm!!

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Exceptional(14)

$511.51

/ Nightly

Private Vacation Home

Updated Ranch in a quiet neighborhood 5 min from the beach and other amenities

Westerly, Rhode Island, United States

Charming, clean, quiet 3 bed 2 bath ranch. Recently furnished with all brand new furniture. Come to the beautiful RI shore!! Nightly, weekly or monthly rates available. Short drive to Atlantic Avenue for beach, dinner, and kid friendly activities. Or, a quick ride to shopping and other sight seeing SO MUCH TO OFFER!! ❤️❤️❤️❤️ brbrCheck out downtown Westerly: Graze Burgers, The Grey Sail Brewery, 2 bookstores, antique shops, many retail shops, pubs, and restaurants. 10 minutes from Watch Hill, 40 minutes from Historic Newport, RI. There are playgrounds and tennis courts for after dinner hours of fun located just up the street at Rotary Park or enjoy a short drive to Watch Hill for ice cream and carousel ride; great for the kids-- or The Ocean House for adults. Foxwoods Resort Casino is 35 minutes away. Mohegan Sun casino is 50 minutes away. Enjoy dining in the many waterside restaurants in our area. Walmart superstore is just 2 minutes away. In the summer there are many free outdoor concerts with free parking.brbrWesterly is another town in Washington County on the southwesternmost tip of the state. With a population of over 17,000 people and an area of nearly 75 square miles, this town serves as a popular resort and beach destination. The history of Westerly dates back to 1661 when colonists established the westernmost Rhode Island settlement. From there, the territory was incorporated in 1669, becoming known as Westerly. Throughout its rich history, Westerly has served numerous purposes, such as being home to a vital fishing industry and having many favored beaches for summer recreation.brbrToday, visitors explore Westerly's coastal region stuffed to the brim with beautiful beaches, marinas, and boatyards for sailing enthusiasts. The downtown area boasts Victorian-era architecture surrounded by shops, restaurants, and galleries that all come together to create a vibrant culture. Along with historical attractions like Wilcox Park and Babcock Smith House Museum, nature lovers can explore excellent wilderness trails in one of the nearby State Parks or National Wildlife Refuge areas, including Ninigret National Wildlife Refuge, John H Burlingame State Park, golf courses, fine dining establishments, day spas, and various recreational activities, from kayaking to sailing charters. It is no wonder that tourists flock here year after year, it is a special place for vacationers.

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$1017.21

/ Nightly

Private Vacation Home

Happy Valley Hill: Secluded 6 bedroom in Westerly less than 2 miles from beach

Westerly, Rhode Island, United States

Tucked on a hilltop minutes from the beach, this 6BR hideaway is made for gathering. With sunny living spaces, shaded patios, and room for everyone, it’s perfect for families or friends who want quick access to Watch Hill, Misquamicut, and downtown Westerly, or a private retreat in a cozy home. Stroll the garden, lounge on the deck, even let the kids claim the bunk room and family room downstairs — beautiful in every season.

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Exceptional(1)

$684.37

/ Nightly

Private Vacation Home

Renovated Coastal Farmhouse Near Beaches

Westerly, Rhode Island, United States

Escape to this beautifully renovated coastal farmhouse, tucked among peaceful woods yet just 5 minutes to the beach (pass available), country club, and scenic wildlife refuge. Bright open spaces, gleaming hardwoods, and room to gather make it perfect for creating lasting memories. Only 10–15 minutes to charming Watch Hill. Relax, unwind, and experience the best of coastal Rhode Island.brbrWoodland privacy. Coastal charm. Minutes to everything.

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$1368.0

/ Nightly

Private Vacation Home

Beautiful 5 BDR Weekapaug Rental

Westerly, Rhode Island, United States

This beautiful Weekapaug vacation home has 5 bedrooms (including a bunk room that sleeps 5), 4 bathrooms and a spectacular property in the Weekapaug Fire District. Walk to beach/tennis/bikes/infared sauna/trampoline/canoe/kayaks included. A 10 min drive from Watch Hill/The Ocean House and just steps away from The Weekapaug Inn and all it has to offer!

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Exceptional(28)

$1129.02

/ Nightly

Private Vacation Home

Misquamicut Waterfront Beach House

Westerly, Rhode Island, United States

The house has 4 bedrooms, a Captains closet with a queen size bed inside it, full kitchen, dining room, living room, 4 decks and 2 full baths. The house comfortably sleeps 8 adults and 2-4 children. Broken down by floor:br—3rd floor has a master suite (bedroom #1) that has a king size bed and day bed with trundle (suitable for children only); master bath has tub/ shower, sink, toilet and washer/ dryer. Across the hall there is a Captain's closet (yes closet) with a queen sized bed (suitable for 2 children or teens). Additionally there is a newly added large sunroom with floor to ceiling windows facing the ocean with king size bed (bedroom #2).br—2nd floor (main living floor) has a full bathroom with shower, kitchen, dining room w seating for 7, living room with triple slider onto the main deck with a large table with seating for 10 people. There are two main level bedrooms- one with 2 twin beds (bedroom #3) and one with a king size bed (bedroom #4). Each bedroom has a sliding door out onto the main deck. There is plenty of room to put a blow up mattress in the living room if desired and there is a door that privatizes the open concept kitchen/ livingroom/ dining room from the rest of the house.brbrThe entire open concept kitchen/ dining room/ living room and all bedrooms (including the sunroom) have air conditioning. The only areas without AC are the hallways, bathrooms and the captains closet.brbrOne code-locked garage bay is provided with beach chairs, umbrellas, sand toys, etc. The other garage bay and first floor (basement) stores our personal property and will remain locked at all times and is off limits.brbrThe town beach is 0.15 miles away and has bath houses and a life guard. The fire district beaches are spread out along Atlantic ave all the way down to the Andrea- your rental includes parking and walking passes to those beaches/ parking lots. There is a walk-on path to the beach right across the street (to the right of the house with the surfboard fence), HOWEVER, this is just for walking along the water. The beach is private property above the high tide watermark— you will be kicked off by the homeowners if you set up chairs and blankets on those homeowners private property.

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Exceptional(28)

$623.87

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Cozy summer cottage, short walk to beach and historic Watch Hill village

Westerly, Rhode Island, United States

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Exceptional(28)

$440.04

/ Nightly

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Custom cottage close to everything-Enjoy long walks on beach without the crowds!

Westerly, Rhode Island, United States

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Exceptional(28)

$489.06

/ Nightly

Private vacation home

45C Haversham - Unique Oak Post And Beam Home In A Secluded Setting

Westerly, Rhode Island, United States

Bed

Bath

Sleeps

Exceptional(28)

$511.51

/ Nightly

Private vacation home

Updated Ranch in a quiet neighborhood 5 min from the beach and other amenities

Westerly, Rhode Island, United States

Bed

Bath

Sleeps

Exceptional(28)

$524.40

/ Nightly

Private vacation home

Perfect 3-bedroom family house in beautiful Westerly, Rhode Island!

Westerly, Rhode Island, United States

Bed

Bath

Sleeps

Exceptional(28)

$536.30

/ Nightly

Private vacation home

Charming Dunn’s Corners Westerly Cape

Westerly, Rhode Island, United States

Bed

Bath

Sleeps

Exceptional(28)

$580.76

/ Nightly

Private vacation home

Entire house 2 miles to Misquamicut Beach- Sleeps 10!

Westerly, Rhode Island, United States

Bed

Bath

Sleeps

Exceptional(28)

$602.57

/ Nightly

Private vacation home

Weekapaug area beach house near beach and pond with Dunes beach pass included.

Westerly, Rhode Island, United States

Bed

Bath

Sleeps

Exceptional(28)

$805.15

/ Nightly

Private vacation home

Renovated Beach Cottage, 1/2 Mile Walk to East Beach

Westerly, Rhode Island, United States

Bed

Bath

Sleeps

Exceptional(28)

$777.48

/ Nightly

Private vacation home

Misquamicut Beach House, Just 1 Mile From the Ocean!

Westerly, Rhode Island, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Westerly, RI

$947.83

$601.92

$811.3

$682.37

$520.6

$1196.19

$818.36

$721.05

$461.34

$684.0

$1869.6

$3617.63

$1434.39

$398.54

$524.4

$511.51

$1017.21

$684.37

$1368.0

$1129.02

Rent a place that suits your needs

Most popular vacation rentals in Westerly

$623.87

$440.04

$489.06

$511.51

$524.40

$536.30

$580.76

$602.57

$805.15

$777.48

Most Popular Cities in Rhode Island