Vacation rentals in Westerly

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Top-rated vacation rentals in Westerly

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

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Top guest favorite
Guesthouse in North Stonington
4.99 out of 5 average rating, 220 reviews

"Mystic Country" Farm Stay at 100 Acre Wood

Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

Guest favorite
Apartment in Westerly
4.89 out of 5 average rating, 123 reviews

Westerly Garden Apartment Minutes Walk to Downtown

Comfortable, spacious apartment walking distance to downtown Westerly with patio, outdoor dining and fire pit. Let DownWest Apartment be your landing pad to enjoy nearby beautiful ocean beaches, historic towns, renowned dining and casinos. Head to the United Theater or the Knick for a night of entertainment and dancing, hop the Amtrak for a night out in Mystic, CT or take a stroll through historic Wilcox Park. Or, grab some fresh lobsters to bring home and enjoy all that DownWest has to offer.

Superhost
Apartment in Westerly
4.87 out of 5 average rating, 141 reviews

Salt & Stone House-1 bedroom Oasis sleeps 4

Downtown 1 bd, 1 bth unit. Park your car and walk downtown to shop, grab a bite to eat, catch a movie at the renovated 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 and living room pullout full size bed. Grocery, Liquor, restaurants, laundromat are all steps away from this well kept secret on a dead end road.

Top guest favorite
Guesthouse in Westerly
4.99 out of 5 average rating, 109 reviews

Ocean Shire Coastal Retreat + Beach Pass

Ocean Shire: Warm modern updated private coastal cottage located 3 miles of stunning beaches (Misquamicut and Watch Hill). Season beach pass included. Kids welcome. 1100 sq. ft, two bedroom, 1.5 bath attached cottage on 1.4 acres. Watch Hill/Ocean House: 5 min. drive Mystic, CT: 10 miles Stonington, CT: 8 miles Newport, RI: 38 miles Wooded yard is a beautiful tranquil outdoor space. Easy access to shops, restaurants, bars, sailing, water sports and beach are all available at your door.

Top guest favorite
Cottage in Westerly
4.97 out of 5 average rating, 111 reviews

Downtown Westerly Beach Cottage Getaway

This beautifully finished home in the heart of downtown Westerly is just steps away from Wilcox park and all the surrounding amenities. In 10 minutes or less, drive to popular Misquamicut Beach or lovely Watch Hill Beach. We are also adjacent to Stonington, Ct and Mystic Seaport. The home is equipped with all essentials needed (Premium beds, bedding, towels, kitchenware, smart TVs, high speed WIFI, basic cable, washer-dryer, central AC and heat). You will not be disappointed in the location!

Top guest favorite
Cabin in Westerly
5 out of 5 average rating, 141 reviews

Autumn Leaves & Winter Fires - Private, Sleeps 7

NEW THIS SUMMER: Westerly Town Beach Pass now INCLUDED! Welcome to Woodhaus! Where, within 5 miles, you can be lounging on the best Westerly OR Charlestown beaches and enjoy shopping and dining in historic downtown. With 3 private acres, you can enjoy a refreshing outdoor shower, bonfire with friends, backyard games, and walking trails. On cooler nights, fire up the wood stove and cozy up with a blanket. We are a dog and kid friendly home! View more photos and updates @Woodhaus_Westerly

Top guest favorite
Guest suite in Stonington
4.99 out of 5 average rating, 304 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 favorite
Home in Westerly
4.97 out of 5 average rating, 142 reviews

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. In the warmer weather, enjoy the outdoor shower after a long hike or trip to the beach.

Top guest favorite
Guest suite in Westerly
4.98 out of 5 average rating, 156 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 favorite
Guest suite in Westerly
4.96 out of 5 average rating, 158 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.

Guest favorite
Home in Westerly
4.97 out of 5 average rating, 151 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 favorite
Apartment in Westerly
4.99 out of 5 average rating, 203 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 Westerly vacation rentals

Quick stats about vacation rentals in Westerly

  • Total rentals

    320 properties

  • Nightly prices starting at

    G$6,259 GYD before taxes and fees

  • Total number of reviews

    13K reviews

  • Family-friendly rentals

    230 properties are a good fit for families

  • Pet-friendly rentals

    90 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Frequently Asked Questions

  • Are there house rentals with a dedicated workspace in Westerly?

    Yes! Work meets play with ease at over 100 house rentals in Westerly featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Westerly have air conditioning?

    Absolutely! We offer over 170 house rentals with air conditioning in Westerly. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westerly have a bbq area?

    Absolutely! We offer over 70 house rentals with a bbq area in Westerly. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westerly have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Westerly. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Westerly?

    Westerly has more than 160 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly house rentals in Westerly?

    Four-legged friends are welcome in Westerly. Choose from more than 70 house rentals for guests traveling with pets.

  • Are there Westerly house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Westerly, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Westerly have wifi?

    Absolutely! We offer over 190 house rentals with wifi in Westerly. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in condo rentals in Westerly?

    Experience the best of Westerly with our condo rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Westerly?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a gym, over 70 homes with a bbq area, over 190 homes with wifi, over 170 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore