Holiday houses in Watch Hill

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Top-rated holiday rentals in Watch Hill

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A welcoming front porch is adorned with yellow flower baskets and potted plants. A comfortable chair is positioned next to a small table, inviting relaxation. Warm light is emitted from a hanging lamp, creating a cozy atmosphere in this outdoor space.
Apartment in Westerly
4.98 out of 5 average rating, 417 reviews

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!

Top Guest favourite
The spacious living area features an open layout with a high post and beam cathedral ceiling, showcasing natural wood finishes. Large windows allow sunlight to fill the space, highlighting the seating area and dining table below. A cozy area rug adds warmth to the floor.
Cabin in Westerly
5 out of 5 average rating, 168 reviews

Sunny Days, Starry Nights | 10 Min to Beaches

WINTER GETAWAY ALERT: Cozy up on the RI Coast! Welcome to Woodhaus Westerly — a peaceful winter retreat minutes from downtown shops, breweries, and coastal walks. Enjoy 3 private wooded acres for starry-night bonfires, winter trails, and cozy nights by the wood stove with blankets, games, and movies. Dog + kid friendly with plenty of space to relax. Perfect for couples, families, or a remote-work refresh. ā˜€ļøBeach Pass returns for Summer 2026! View more photos and updates @Woodhaus_Properties

Guest favourite
Tiny home in Middletown
4.98 out of 5 average rating, 175 reviews

Cozy coastal tiny house getaway

Situated on Easton's Point, brand new ocean front tiny house looks across to Mansion Row with access to a rocky beach for lounging, swimming, or fishing. The property is close to downtown Newport & ideally located between three beaches. The cozy unit has a queen bed, full bath & kitchenette with coffee maker, fridge, and toaster oven. There is a small deck with ocean views, access to ocean front, outdoor shower and off street parking. We provide beach chairs, a beach umbrella and towels.

Guest favourite
Apartment in Stonington
4.94 out of 5 average rating, 327 reviews

Mystical Ocean View in Historic Stonington Borough

Enjoy stunning ocean views of Stonington Harbor and Fishers Island Sound from multiple floors of this spacious, comfortable apartment for 6. Located in historic Stonington Borough, Connecticut's oldest village, you can relax in the private library, then explore this picturesque area with acclaimed restaurants, shops, and museums all within walking distance. And with Downtown Mystic, I-95, and RI's beaches just a short drive away, you can have it all, located half way between Boston and NYC!

Top Guest favourite
An outdoor patio features a seating area with cushions in calming colors. A grill is positioned against the wall, and the space is surrounded by grassy areas and low-maintenance landscaping. Large windows provide a view of the indoors, enhancing accessibility.
Home in Westerly
5 out of 5 average rating, 134 reviews

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.

Top Guest favourite
A bright and airy kitchen features white cabinetry and wooden shelves. A central island with two stools provides a casual dining area. Natural light floods the space, accentuating the modern appliances, including a stainless steel refrigerator and a microwave. Fresh flowers add a touch of color.
Guest suite in Stonington
4.98 out of 5 average rating, 367 reviews

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!

Top Guest favourite
An aerial view showcases a traditional New England-style home with a distinct green roof. A private pool with steps is situated on a spacious deck, surrounded by lounge chairs and tropical plants. Scenic outdoor areas for relaxation and recreation are visible on the property.
Home in Stonington
4.97 out of 5 average rating, 251 reviews

Perfect New England Getaway has a pool/ hot tub

traditional New England style that is not just a great home, but a great vacation compound with lots of amenities and outdoor living spaces. Enjoy recreational activities on land and sea that abound locally. Mystic, Stonington Borough, Westerly, and Watch Hill are all close IMPORTANT INFORMATION: Please be advised Stonington, CT has a STRICT OUTSIDE Noise ordinance after 10pm that is enforced by the Police. If a report is generated for any reason , you will forfeit your deposit.

Top Guest favourite
A bright living space features a white brick fireplace, complemented by a black fire screen. Above the mantel, a large, minimalistic artwork with a sun motif is displayed. Shelving holds neatly stacked firewood and decorative items, enhancing the room's inviting ambience.
Home in Weekapaug
4.98 out of 5 average rating, 125 reviews

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.

Top Guest favourite
Guesthouse in Westerly
4.99 out of 5 average rating, 117 reviews

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. šŸ–ļø Watch Hill/Beaches: 5 mins āš“ Historic Mystic: 18 mins šŸ° Newport: 50 mins āœˆļø 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.

Top Guest favourite
A spacious outdoor area features a wooden deck with multiple seating options, including comfortable lounge chairs and a dining table under a large umbrella. Surrounding planters with greenery contribute to the natural setting, while a gas grill is positioned for shared use.
Guest suite in Westerly
4.98 out of 5 average rating, 167 reviews

Private suite close to beaches and downtown.

The Ruedemann Suite is situated off of our main house in a quiet neighborhood. We are located 3 miles from Misquamicut Beach & Watch Hill. Historic Downtown Westerly with its thriving restaurant, arts & music scene is 1.5 miles from the house. Take a short drive to Stonington or Mystic for shopping or local vineyards. Feeling lucky? Mohegan Sun & Foxwoods Casinos are close by! Newport & Providence are a 45-minute drive. Follow on the gram @ruedemannsuite

Top Guest favourite
A stone staircase descends towards a serene pond, bordered by lush greenery and vibrant hydrangeas in bloom. The calm water reflects the surrounding trees, creating a peaceful natural setting.
Guest suite in Westerly
4.96 out of 5 average rating, 159 reviews

Room with a View on Spring Pond

Fab newly decorated suite in 1957 home set on a private pond near Watch Hill, RI. Private entrance with mini kitchen, fridge,microwave, portable induction cooktop,toaster,coffeemaker- every thing but the kitchen sink! Please note: there is no kitchen sink nor oven. Ensuite bath with new towels,robes,linens,and bedding. Outdoor shower ( in addition to an indoor one!) ,grill,lounging area. Near beaches,music,food, Mystic Ct attractions. Great relaxing venue.

Top Guest favourite
The turn of the century home features a welcoming entrance with a decorative railing and front porch. An American flag is displayed, and lush landscaping complements the exterior. Sunlight highlights the structure, ensuring a bright and inviting appearance.
Apartment in Westerly
4.99 out of 5 average rating, 209 reviews

THE COOL HOUSE

Spacious two bedroom apartment in beautifully maintained turn of the century home, private entrance. Huge windows keeps this third-floor apartment bright and sunny all day. Within walking distance of Amtrak, downtown restaurants and bars, 10 minute drive to RI beaches, Historic Watch Hill. Also drive to Newport, Casinos and Mystic,CT. This home is a perfect get-a-way. WiFi

Popular amenities for Watch Hill holiday rentals

Quick stats about holiday rentals in Watch Hill

  • Total holiday rentals

    Explore 10 holiday rentals in Watch Hill

  • Nightly prices starting at

    Watch Hill holiday rentals start at $181Ā AUD per night before taxes and fees

  • Verified guest reviews

    Over 170 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    10 of Watch Hill holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Watch Hill rentals

  • 4.9 Average rating

    Watch Hill stays are highly rated by guests—averaging 4.9 out of 5!

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