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, 414 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
An inviting living space is characterized by high post and beam cathedral ceilings, with a floor-to-ceiling fieldstone fireplace as a focal point. Cozy seating is arranged around a central coffee table, with warm lighting provided by string lights. The area reflects a blend of rustic charm and modern comfort.
Cabin in Westerly
5 out of 5 average rating, 165 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. ☀️Beach Pass returns for Summer 2026! View more photos and updates @Woodhaus_Properties

Guest favourite
A glass desk is positioned beside large windows, offering views of the water and sky. A cozy chair with a fluffy seat cover complements the desk. A stack of books, binoculars, and a soft-lit lamp are arranged on the desk, enhancing the workspace atmosphere.
Apartment in Stonington
4.94 out of 5 average rating, 324 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
A modern kitchen features white cabinetry and granite countertops. Stainless steel appliances, including a microwave and oven, are visible. A large island with seating accommodates several stools, and overhead pendant lighting provides bright illumination.
Home in Westerly
5 out of 5 average rating, 130 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
Guest suite in Stonington
4.98 out of 5 average rating, 358 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
A charming two-story house features a shingle exterior and large windows, providing ample natural light. Lush green grass surrounds the home, complemented by mature trees offering shade. A small front porch with white chairs invites relaxation while enjoying the serene landscape.
Home in Stonington
4.96 out of 5 average rating, 142 reviews

Unobstructed Water Views & Huge Patio with Hot Tub

Gorgeous water views abound! Let you and your loved ones take in the serenity and charm as you arrive at our home set back from the road, facing the Pawcatuck River. Take in the view from most rooms of the house. Wake up with your first cup of coffee gazing at the river from the sunroom sofa, before a day at the beach or sight-seeing at picturesque towns nearby! After kayaking or sunning at nearby fabulous beaches, enjoy a BBQ dinner, and relax in the hot tub. Be our guest and enjoy!

Top Guest favourite
A charming three-story home features a classic gambrel roof and a light blue exterior. The front porch is accented with white railings and hanging planters. Lush greenery surrounds the property, providing a secluded atmosphere. A well-maintained lawn lines the pathway leading to the entrance.
Home in Westerly
4.95 out of 5 average rating, 421 reviews

Spring Weekend Beach Escape: Walk to Coffee & Yoga

Spring in Westerly is a hidden gem. Cool mornings, quiet beaches, and no summer crowds. Walk to coffee, take a yoga or sculpt class at BarreCoast just steps away, then spend the afternoon shopping, exploring Watch Hill, visiting vineyards or strolling the shoreline. This is the perfect spot for: - A girls’ weekend - A couples’ coastal escape - A wellness reset - Remote work with beach walks in between - Spending the night post theater or Casino Everything is open — just calmer.

Top Guest favourite
Guesthouse in Westerly
4.99 out of 5 average rating, 115 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. 🏖️ 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.

Top Guest favourite
A serene bedroom features a spacious bed adorned with soft grey linens. Two bedside tables, each with a lamp, flank the bed. A vibrant piece of artwork and a framed print add color to the walls, enhancing the room’s inviting ambiance.
Guest suite in Westerly
4.98 out of 5 average rating, 164 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
A charming two-story gray house is framed by a neatly kept garden with green foliage. Prominent features include a bright blue front door and a fenced yard, enhancing privacy. The structure is accented by evenly spaced windows, allowing for ample natural light.
Home in Westerly
4.98 out of 5 average rating, 163 reviews

Cute and Close to Beaches and Town

A cute comfortable 2 bedroom 2 bath home with summer beach parking pass. Recently updated and furnished. A fenced in backyard. Allowing pets. Close to all in Westerly and South County. Grey Sail brewery, shops, restaurants. A 5 minute walk to restaurants, About a mile to Downtown Westerly and Wilcox park. 4 Miles to Misquamicut beach and Watch Hill. Central AC. Fenced in back yard allowing pets Great place to rent year round!

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, 206 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 $221 NZD 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 Beachfront, Gym and BBQ grill across Watch Hill rentals

  • 4.9 Average rating

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

  1. Airbnb
  2. United States
  3. Rhode Island
  4. Washington County
  5. Westerly
  6. Watch Hill