Holiday rentals with outdoor seating in Westerly

4.99 out of 5 average rating, 116 reviews

Apartment in Westerly

Heathers On High Street King Bed/Twin Bed

Experience Westerly life like a Local! Enjoy this centrally-located Apartment close to Downtown. Easy highway access to the Beach and Casinos. Free Parking with Private entrance opens to a courtyard with Gazebo Sitting area and a Grill just for you! The 2 Bedroom Apartment is located on the 2nd floor with a Full Kitchen/Living Room combination, 1 Bathroom, Washer/Dryer and Central Air. The Master Bedroom has 1 King Bed with a new Nectar Mattress. Second smaller bedroom has a Twin Pillowtop Bed

Guesthouse in North Stonington

A serene landscape is presented, featuring expansive green fields under a softly glowing sunrise. Two rustic buildings are visible: a barn with classic doors and a white cottage, both surrounded by lush trees and open space, reflecting the peaceful countryside setting.

4.99 out of 5 average rating, 223 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.

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.

4.95 out of 5 average rating, 405 reviews

BarreCoast Stay: beach pass, casinos, vineyards

Welcome to BarreCoast Stay! My name is Kristen and I am the owner of this beautiful home, as well as BarreCoast the top barre, yoga, boxing studio in RI. This year-round getaway is great for a family vacation, girls or couples trip . This impeccable home sleeps 6 and is in an ideal location. A short 10 minute drive to beaches, 2 min walk to BarreCoast, High Tide Juice Bar, Pizza, Junk Java Coffee Shop, 5 min drive to downtown restaurants, nightlife and Wilcox Park. 20 minutes from casinos.

4.89 out of 5 average rating, 133 reviews

A welcoming entrance features a blue door with a small window and the number 37 displayed. Steps made of stone lead up to the door, flanked by a vibrant blue pot of flowers, adding a touch of color to the exterior.

Apartment in Westerly

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.

5 out of 5 average rating, 149 reviews

An inviting living area is displayed, featuring high cathedral ceilings with exposed wood beams. A cozy couch faces a television, while a beautifully decorated Christmas tree adds festive charm. Soft lighting creates a warm ambience, inviting relaxation and gatherings.

Cabin in Westerly

Fireside Delights & Snowy Nights - Sleeps 7

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

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.

5 out of 5 average rating, 123 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.

4.99 out of 5 average rating, 113 reviews

A blue entry door is featured, equipped with a keypad lock for self check-in. The door displays a decorative door knocker at the center, surrounded by five raised panels, creating a classic and welcoming entrance.

Guesthouse in Westerly

Ocean Shire Coastal Retreat + Beach Pass

Relax at this warm modern private coastal cottage. Located 3 miles of Misquamicut and Watch Hill beaches. Season beach pass included. Kids Welcome! 1100 sq. ft, two bedroom, 1.5 bath attached cottage on 1.4 acres. Taylor Swift's Watch Hill home: 3 miles Ocean House Watch Hill: 3 miles Mystic, CT: 10 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.

Guest suite in Stonington

4.99 out of 5 average rating, 324 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!

A spacious dining area is highlighted by a wooden table surrounded by elegant chairs. Natural light pours in through large windows, illuminating the inviting living space with a comfortable sectional couch and a wall-mounted TV. Decorative pendant lights enhance the modern kitchen's open layout.

4.97 out of 5 average rating, 152 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.

4.98 out of 5 average rating, 163 reviews

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

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

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.

4.97 out of 5 average rating, 159 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!

5 out of 5 average rating, 107 reviews

Tiny home in East Lyme

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Popular amenities for Westerly outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.96 out of 5 average rating, 143 reviews

A side view of a beachfront home showcases large windows offering views of the water. Blue planters filled with greenery adorn the exterior, while a bright turquoise door adds a pop of color. A wooden walkway leads towards the home, framed by the blue sky.

Home in Narragansett

The Landing

4.92 out of 5 average rating, 128 reviews

A charming white house with a welcoming porch is framed by a well-maintained garden. Pathways of stone lead to the entrance, surrounded by vibrant shrubs and flowers. The clear blue sky adds brightness to the serene setting.

Home in Groton

1 Bedroom Suite in the Heart of Mystic

4.98 out of 5 average rating, 134 reviews

A spacious front porch features contemporary outdoor seating with scenic views of the ocean. The deck is surrounded by a low railing and includes a table, inviting relaxation while enjoying the coastal surroundings. Lush greenery and a pathway are visible beyond the porch.

Home in Narragansett

The Surf Shack - Ocean Views From Every Room

4.98 out of 5 average rating, 100 reviews

A bright living area features a large windowed wall, providing expansive views of the waterfront. A light-colored sofa and two armchairs are arranged around a central coffee table, creating a cozy seating space. Natural light floods the room, enhancing its inviting atmosphere.

Home in Narragansett

Seaside Serenity

4.93 out of 5 average rating, 119 reviews

A wide view of a sandy beachfront stretches along the coastline, bordered by calm blue waters under a clear sky. Lush greenery can be seen in the distance, suggesting a nearby park or recreation area. Several individuals are spaced along the shore enjoying the beach.

Home in Waterford

Salty Breeze - Waterfront Cottage on the Cove

4.93 out of 5 average rating, 265 reviews

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

Romantic Getaway at The Lake!

5 out of 5 average rating, 144 reviews

A charming red colonial home stands proudly beside a tree-lined street. The white picket fence surrounds the front yard, which is adorned with greenery and patriotic bunting. Large trees provide shade, creating a welcoming atmosphere for visitors.

Home in Old Mystic

Nautical "Hallmark" Retreat~ 5 Toasty Fireplaces!

4.9 out of 5 average rating, 163 reviews

The living area features a large sectional sofa with a throw pillow, a dark coffee table, and a dining area with a wood table. Sliding glass doors open to a scenic view of the Thames River and the outdoor deck.

Home in Montville

Thames River Cottage · Near Casinos + USCGA

Apartment rentals with outdoor seating

4.99 out of 5 average rating, 107 reviews

A cozy bedroom is presented with a light-colored bedspread and a decorative pillow on the spacious bed. Vertical blue and white stripes adorn the wall behind, complemented by a round mirror. A soft lamp and a small plant add subtle accents beside the bed.

Apartment in Stonington

Mystic Bungalow - 6min Walk Downtown!

4.94 out of 5 average rating, 316 reviews

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

Mystical Ocean View in Historic Stonington Borough

4.88 out of 5 average rating, 113 reviews

A cozy living area features a modern orange sectional sofa adorned with blue throw pillows. Natural light filters through the blinds of two windows, illuminating the space. A round coffee table with a decorative centerpiece sits on a patterned area rug, complemented by a light grey armchair.

Apartment in Mystic

Big Family 2BR, Central Mystic w/ parking - 6A

4.86 out of 5 average rating, 445 reviews

The main living area showcases a cozy sofa, complemented by a vibrant throw pillow. A round coffee table sits atop a patterned area rug. Natural light filters through the windows, illuminating the space and enhancing the modern decor.

Apartment in Mystic

Super Cute & Cozy Apartment in Downtown Mystic!

Apartment in South Kingstown

A charming exterior view of a house is presented, featuring a stone chimney and a screened porch with yellow trim. Lush green grass and various plants frame the pathway, inviting a sense of greenery and tranquility.

4.98 out of 5 average rating, 141 reviews

Cute and Convenient

Superhost

A cozy living area features a dark leather sofa with bright yellow and patterned throw pillows. A small round wooden coffee table sits in front, complemented by a decorative plant on top. Art pieces adorn the walls, adding a touch of color to the neutral tones.

Apartment in Westerly

4.87 out of 5 average rating, 145 reviews

Salt & Stone House-1 bedroom Oasis sleeps 4

Apartment in South Kingstown

A modern kitchen features wooden countertops with three bar stools positioned at a breakfast bar. Shelves hold glassware and decorative bottles. Natural light enters through a window, illuminating the granite counters and stove area. Additional seating is visible in a cozy dining nook.

4.98 out of 5 average rating, 252 reviews

"The Broody Hen" Farmhouse (2.5mi to beach)

4.97 out of 5 average rating, 157 reviews

A bright sleeping area features a spacious bed with light-colored bedding, positioned beside large windows dressed with gray curtains. A minimalist TV stand holds a television, with a colorful wall art piece providing a vibrant accent against the neutral walls.

Apartment in Groton

Rare find beautiful studio on the Mystic River

Condo rentals with outdoor seating

4.93 out of 5 average rating, 108 reviews

Condo in Newport

Wharf Harbor Holiday in Downtown Newport

4.96 out of 5 average rating, 189 reviews

A cozy sleeping area features a wooden bed with a navy blue anchor-patterned duvet cover. Two large windows allow natural light, while a leafy plant adds a touch of greenery. A vintage trunk rests at the foot of the bed, complemented by a patterned area rug.

Condo in Newport

cozy 1 bedroom apartment with parking & balcony

4.95 out of 5 average rating, 162 reviews

A spacious bedroom features elegant floral-patterned wallpaper, a large bed with layered white linens, and a decorative pillow. Natural light fills the room through multiple windows, enhancing the calming atmosphere. A round mirror and a bedside light fixture add functional decor.

Condo in Fox Point

Mon Reve Cottage Suite by PVDBNBs (2 bed, 1 bath)

5 out of 5 average rating, 242 reviews

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

Condo in The Hamptons

Montauk Waterfront Condo w/ Sunset Views

4.98 out of 5 average rating, 165 reviews

A living area features a comfortable sofa and two armchairs, arranged around a rustic coffee table. A fireplace is set into a stone mantel, and a large television is mounted on the wall. Sliding doors lead to a private balcony, allowing natural light to fill the space.

Condo in Norwich

The Vacay Villa

4.99 out of 5 average rating, 217 reviews

Condo in Norwich

Peaceful Oasis steps from Mohegan Sun

4.89 out of 5 average rating, 159 reviews

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

Condo in North Fork

Waterfront Autumn Escape in Wine Country: 2BR