Home Vacation Rentals By Owner In Westerly, RI

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$2529.38

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Private Vacation Home

Watch Hill Luxury by the Sea, Iconic 1852 School House, Beside Ocean House Hotel

Westerly, Rhode Island, United States

“Formerly part of the Ocean House Cottage Collection, The Schoolhouse is a rare standalone home (Fully remodeled and refurnished with Restoration Hardware Top of The Line Furnishings) located just steps from the resort on the ocean side of Westerly Road. Enjoy full privacy and space while being just a few steps to Ocean House dining, spa, and beach access — “Featured in Architectural Digest’s ‘15 Incredible Former Schoolhouses You Can Spend the Night In,’ this historic home is now exclusively available for the first time on VRBO.”brbrAlthough The School House is brand new to VRBO, guests can book with complete confidence. The property is owned and managed by a host with 17 years of experience renting luxury homes in Rhode Island, including 2 Arrow Wood Trail, a premier VRBO property with over 53 five-star reviews. The School House is a high-end home, newly made available on VRBO for the very first time, and this is the only reason reviews are not yet posted. The School House is a luxury Watch Hill home, with a proven five-star track record and a property that has already met the strict standards of the Ocean House Cottage Collection Program for many years. brbr Steps from Ocean Housebr • Private standalone cottagebr • Ocean-side locationbr • Boutique luxury staybrbrStep back in time while enjoying every modern comfort at The School House, a historic 1852 school lovingly transformed into a cozy oceanfront bungalow. Located directly beside the iconic Ocean House Hotel, this cottage offers the best of both worlds: the charm of Watch Hill history and the luxury of seaside living—with direct access to a residents’ beach, monitored by security. brbrRather than a small condo with limited space, enjoy the comfort of your own intimate coastal yard - a peaceful spot with ocean views, alfresco dining, evening cocktails and a picture-perfect backdrop of the Ocean House Hotel will make you feel right at home.brbrA Storied PastbrbrOnce a classroom for local children and later “Miss Stevenson’s Little Shop” for over 30 years, the cottage was ultimately re-imagined as a private residence. Its heritage lives on through soaring vaulted ceilings and original hand-hewn beams revealed during renovation—blending old-world craftsmanship with an airy, coastal design.brbrComfort & LayoutbrbrThe open-concept plan creates a light-filled space where the living room, kitchen, and dining area flow together beneath dramatic beams and ocean-view windows. French doors lead to a private porch overlooking views to the ocean, while a newly landscaped side yard offers a perfect spot for cocktails, grilling, or dining al fresco against a backdrop of ocean breezes.brbr2 Bedrooms, 2 Baths, Sleeps 5brbrPrimary suite with king bed and en-suite bathbrbrGuest room with two twin beds and full bathbrbrLiving area with pull-out sofa and fireplacebrbrAmenitiesbrbrAir conditioningbrbrFull kitchen with Bosch washer/dryerbrbrPrivate driveway parking for 2 vehicles (rare in Watch Hill)brbrPorch with ocean viewsbrbrLandscaped 40-foot side yard with dining areabrbrDirect access to neighborhood, security-patrolled beachbrbrThe ExperiencebrbrWhether you’re enjoying your morning coffee steps from the sand, savoring a glass of wine on the patio at sunset, or strolling next door for cocktails or dinner at the Ocean House, your stay feels like a private suite within a five-star resort—yet with the privacy and comfort of your own seaside cottage.brbrThe School House is sheer Watch Hill perfection—historic, charming, and just steps from your own private residents’ beach.
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Bath 2

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Sleep 6

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Exceptional(19)

$8037.0

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Private Vacation Home

SPECTACULAR 5 BR/3BA HOME - WALK TO BEACH - WATCH HILL!

Westerly, Rhode Island, United States

The perfect getaway combining sophistication, comfort and charm. Spectacular 5 bedroom, 3 bath architecturally designed 3500sf home with 2 levels of incredible space and light. Located just a short walk to East Beach and minutes to Watch Hill Village, the Ocean House, shops & restaurants. In a lovely neighborhood nestled between the exclusive villages of Watch Hill and Weekapaug and bordering the Misquamicut Club golf course, this beautifully decorated home has it all. Hardwood floors & central air throughout. Available for Weekly & Monthly rental or minimum of 3 nights (off-season).brNo Pets/No Smoking Permittedbrbr1st Floor Level: Large fully equipped kitchen with Quartz counters and stainless steel appliances, dramatic Great Room with vaulted ceiling, gas fireplace and French doors to mahogany Deck. Dining area with pine farm table & chairs, Living area with built-in's, flat screen TV with Apple TV. 2 Guest Bedrooms (one with a Queen bed and one with twin beds) and a full bath on 1st floor.brbr2nd Floor Level: Ensuite Primary Bedroom with Queen bed, French doors and seasonal water views, Bath with glass tile, shiplap detail, walk in shower. 2nd Primary Bedroom with Queen bed, sitting area and French doors. Guest Bedroom with Queen bed. Shared Full Bath with walk-in shower. Vaulted ceiling Loft sitting area with desk provides privacy and space to read or work. Laundry area with full size washer & dryer.brbrProperty Description: French Doors lead to a large Mahogany deck and stone/Belgium block patio overlooking professionally landscaped perennial gardens and expansive, level backyard. Teak chairs, chaise lounges and Adirondack chairs and a side Deck with teak dining table/chairs provide many areas for relaxing and entertaining complete with a great outside shower/cabana. brbrIncluded: brLinens, Beach towelsbrGas GrillbrBackpack Beach ChairsbrUmbrellasbrMultiple Bicycles
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Bath 3

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Sleep 10

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Exceptional(4)

$1568.0

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Condo

The Saltbox - Watch Hill's Award-Winning Waterfront Retreat.

Westerly, Rhode Island, United States

Nestled between Watch Hill Village and Napatree Point Beach, The Saltbox sits just 87 steps from the captivating white sands of the coast. Featuring unobstructed views of the ocean from EVERY window, you’re sure to feel as if you’re living in a painting as luxury sailboats cruise in front of you. Lovers of sunrises and sunsets, rejoice! Treat yourself to a complimentary coffee or tea brewed from our Keurig and settle into the oceanfront balcony for the sunrise and bayside deck for the sunset.brbrCentrally-located above the boutique shops in the village of Watch Hill, The Saltbox is seconds away from the arts, entertainment, restaurants and beaches that make Watch Hill one of America's best kept secrets. brbrListen to the laughter of children and adults alike from the beach-facing deck while watching the oldest Merry-Go-Round in the United States spin slowly. brbrAptly named The Saltbox, it's a nod to our neighbor, Taylor Swift, with her home, Holiday House, just a four minute walk away.brbrINTERIORbrKitchen: Featuring most everything you'd need to craft a Michelin Star-worthy meal, the open kitchen includes a four top electric GE stove and oven, GE microwave, GE refrigerator and freezer combo, ice maker, toaster oven, high-end Viking pots and pans, cooking utensils, cookbooks, and a generous selection of complimentary oils and spices. Dishwasher pods, dish soap, and garbage bags are provided for your convenience. Three stools at the kitchen island allow for several seating options in living space. brbrLiving Room: Large windows and a skylight allow for wonderful views of the ocean and plenty of natural light to illuminate the space. A sizeable and remarkably comfortable sectional couch offers fantastic views of the TV, water, and living space. Turn on the electric fireplace, snuggle in with the cozy throw pillows and blankets, and experience a level of relaxation you didn't know was possible.brbrDining Area: With space for up to six people, the Crate & Barrel natural white oak solid wood dining table is the finest gathering spot for all of your meals. Including three individual chairs, cushioned bench seating, and a massive mirror that reflects the ocean, we provide the Michelin Star setting, you just need to provide the provisions. brbrBeverage Station: Whether you fancy tea, coffee, or a cocktail, the beverage station at The Saltbox has you covered. Our beverage station includes a Keurig with a variety of complimentary K-Cups, kettle, foam frother, and nearly every type of glassware you could desire for an adult beverage. brbrWasher & Dryer: A GE double-stack washer and dryer are provided for your use. A complimentary starter set of detergent and dryer sheets are provided. brbrTelevisions: Experience streaming like you never have before. The Saltbox features 43 Samsung 4K Picture Frame Smart TV's in the living room and bedrooms. When not in use, these televisions turn into works of art with no blue light.brbrMaster Bedroom: Overlooking the ocean, the master bedroom features a king-sized Tempur-Pedic mattress topped with four Beautyrest Black down alternative pillows and 640 thread count sheets and pillowcases. Furnishings include a designer dresser, full-length mirror, two changing chairs, two side tables, and laundry baskets. Two umbrellas are available for use during your stay, located in the closet. brbrGuest Bedroom: Overlooking the seafront marina cove, the guest bedroom features a queen-sized mattress topped with four Beautyrest Black down alternative pillows and 640 thread count sheets and pillowcases. Furnishings include a vertical chest, a changing chair, side table, and laundry basket. Two umbrellas are available for use during your stay, located in the closet. brbrBathroom: The Saltbox has one bathroom including a freestanding shower with a handheld showerhead, perfect for those days spent at the beach. The large vanity will ensure everyone has space for their travel accessories. Leave your travel bottles behind, your stay includes complimentary white tea and coconut shampoos, conditioners, body soaps, body wash, and body lotions from the Infusé Hotel Collection. A hair dryer, steamer, iron and ironing board are also provided. Relax and take in the sights from the oceanfront window. brbrEXTERIORbrOceanfront Deck: Featuring a fully covered, unobstructed view of the water, the oceanfront deck is the perfect place to drink your coffee and watch the breathtaking sunrise of Watch Hill. The large outdoor couch, coffee table, and bar cart are wonderful for connecting over a meal outside. brbrBayside/Village Balcony: Breathe in the saltwater as you watch the sunset on the balcony facing the marina bay with a cocktail and snacks. With two swivel patio chairs and a coffee table, you can go back and forth from watching the sailboats depart to people watching as crowds make their way to the waterfront shops of Watch Hill.brbrStorage: We have a small storage unit located underneath the condo. We invite our guests to use the high chair, pack and play, beach chairs, beach umbrella, footballs, boogie board, casino card games, Say Anything card game, What Do You Meme card game, Spikeball, Can Jam, 76 can cooler, and 32 can cooler. We just ask you to return the items to where you found them. brbrMOST IMPORTANTLY:brWe're pet friendly! We welcome up to two furry family members during your stay at The Saltbox and offer complimentary doggie bags and treats. brbrBring the kids! We have a pack n' play and high chair for your family.brbrAre you planning to host a bachelor(ette), engagement party, work meeting, or professional photoshoot Send us a message and we'd be happy to assist with coordinating the details.brbrGuests will have exclusive access to The Saltbox during their stay. When staying at The Saltbox, you'll have two complimentary private parking spaces reserved directly in front of the condo on the oceanfront side of the property in the private parking area. This is a must have during the busy season where public parking is VERY limited. Access to both Napatree Point Beach and East Beach, both less than a five minute walk from The Saltbox.brbrWe're thrilled to welcome you to The Saltbox. We're available for you any time throughout your stay. If you have any special requests or need concierge services our team would love to assist.
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Bath 1

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Sleep 4

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Exceptional(63)

$571.14

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Private Vacation Home

We call it Ponder!

Westerly, Rhode Island, United States

Waterfront home with a spectacular view on a 1+ acre lot with a large, manicured lawn and a private foot dock to one of Rhode Island’s famous salt ponds. Ponder, as we fondly refer to it, has a wonderful enclosed porch overlooking Winnapaug Pond with expansive ocean views. brbrLocated within minutes of the Misquamicut and Watch Hill BEACHES (dunes pass to the Misquamicut State Beaches included with rental for all peak-season weeks), with easy access to Foxwoods and Mohegan Sun casinos, Mystic Seaport, Mystic Aquarium, and fantastic dining in Westerly, Watch Hill, Stonington, Mystic, and elsewhere. Just 35 minutes to Newport.br brThere is a public golf course, the Winnapaug Golf Club, located within walking distance, and multiple public tennis courts can be found in the area.brThe house has a large living room that opens to the enclosed porch and a combined kitchen/dining room that overlooks the pond.brFour bedrooms:br• Upstairs master bedroom with king and en suite bathroombr• Second upstairs bedroom with single bedbr• Downstairs room with two single beds br• Downstairs room with full sized bedbrTwo full baths, one with a shower and one with a bath/shower, and one half bath. brbrEasily accessible from the Westerly Amtrak station and T F Green Airport in Providence, and just a few minutes from the Westerly State Airport, which provides daily flights to Block Island.brbrbrKeywords: ocean view, well-equipped home, convenient to beaches and shopping, private dock
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Bath 2

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Sleep 6

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Exceptional(68)

$1400.57

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Private Vacation Home

Summer Wind Beach House!

Westerly, Rhode Island, United States

Gather together for an amazing time with family and friends! Light and bright 3800 sf open floor plan. Central air, fireplace, 7 TV's and 4 1/2 baths. Incredible entertainment room with kitchen, 60 TV, pool table, video library, Direct TV, Netflix and board games. brThere is something for everyone to enjoy in the area. Multiple beaches 1.5 miles away that have free concerts, drive in movies and car shows. Try some water sports, bike riding, mini golf, go karts or batting cages. Rotary Park has 4 tennis courts, beach volley ball, basketball and playgrounds. Visit Watch Hill for a walk on Napa Tree Point. Kids can go for a ride on the historic Watch Hill Flying Horse Carousel then share some pizza and ice cream. Try some golf nearby, maybe a fishing charter, whale watching or a tour of the lighthouses. Visit the many farmers markets and wineries. Take a ride to Narragansett and see Judith Point Lighthouse then catch the ferry to Block Island for lunch and rent some scooters. Enjoy a day in Newport and eat, shop, visit the mansions or take a walk on the cliff walk. Foxwoods and Mohegan Sun Casinos are very close. Take in the beauty of Mystic Aquarium and Seaport or perhaps go to the incredible restaurants in Mystic as well as nearby Stonington. Nature enthusiasts Ninigret Park in Charlestown only miles away! A 227-acre park features a state-of-the-art playground, ball fields, ten-speed bike course, tennis and basketball courts, picnic areas and a freshwater swimming pond with public beach and hiking as well as the Frosty Drew Conservatory. Whatever activities you enjoy everything is close enough to have fun filled days and star filled nights to make great memories!brbrRates are for up to 14 people. Additional guests are $75 per person per night.
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Bath 4

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Sleep 17

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Exceptional(18)

$374.9

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Cottage

Private Watch Hill Cottage 5 Min. Walk to Beach

Westerly, Rhode Island, United States

An alternative to generic condominiums, our unique little cottage is in the heart of Watch Hill. You can walk to two beaches, the oldest 'flying horse' carousel in the U.S., and shops and restaurants in minutes. The cottage is also a short walk from the Ocean House resort hotel and the Watch Hill Chapel. brbrThe Ice House was originally the kitchen/ice house for the larger home on the property, which was later converted to a separate home. The house has a loft-like first floor, with open living and dining room, and a full kitchen with counter seating. There is a new flat screen TV, a pull out couch, and a vintage 1930's Hoosier cabinet and dining set for four. The bathroom is also located on the first floor, has a 'claw foot' tub with shower, and mini washer and dryer units. The cottage has a Caribbean color scheme overall, with a mix of vintage and contemporary furnishings and art. brbrOn the second floor, the master bedroom has an antique double bed with romantic net canopy. The second bedroom has two antique iron twins and is perfect for families with children. Both bedrooms are air conditioned. Outside the bedrooms is a cozy sitting area with a vintage rattan couch, chair, computer desk and small flat screen TV. brbrPlease note that, while the cottage sleeps 6 in a pinch, we will rarely accept a reservation for 6 adults due to the size of the house and the septic system. brbrThe deck on the front of the house has a dining table with umbrella, chairs, occasional tables and a small grill. Please note that the cottage does not have a lawn - but we do have a lovely deck for al fresco dining and cocktails. And the large public park area at the gazebo on the harbor is great for Frisbee and ball play.brAlso please note that there is parking for 2 cars maximum. If both are very large (large SUVs for instance) there will not be room for 2.brbrbrbrKeywords: Cottage, house, bungalo
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