Family-friendly vacation rentals in Westerly

4.99 out of 5 average rating, 115 reviews

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 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.

4.98 out of 5 average rating, 410 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!

4.95 out of 5 average rating, 405 reviews

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

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.

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.

4.89 out of 5 average rating, 131 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

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.

4.87 out of 5 average rating, 145 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.

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

4.97 out of 5 average rating, 114 reviews

A single-story home is presented with a grey exterior and a symmetrical design. The property features neatly trimmed shrubs and a well-maintained lawn. A driveway leads to a garage, while a pathway directs toward the front door, framed by small steps and a welcoming porch.

Cottage in Westerly

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!

4.99 out of 5 average rating, 909 reviews

The exterior view features a small wooden cabin surrounded by vibrant green trees. A stone path leads to a seating area, comprising four metal chairs and a table. Inside, the cozy octagonal space is lit by natural light filtering through several windows, showcasing a full-sized bed adorned with a colorful patterned quilt.

Tiny home in Norwich

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Guest suite in Stonington

4.99 out of 5 average rating, 322 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!

4.97 out of 5 average rating, 152 reviews

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.

Home in Westerly

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

Popular amenities for Westerly family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 223 reviews

Guest suite in Mansfield

Cozy private apt 8 mins from UCONN - solar powered

4.98 out of 5 average rating, 155 reviews

A patio area features grey stone flooring with a round metal table and four stylish chairs under a large blue umbrella. Vibrant yellow flowers surround the seating arrangement, providing a cheerful touch to the outdoor space. The yellow door of the tiny house is visible in the background.

Tiny home in Elmwood

Tiny house get-away with a Yellow Door

4.88 out of 5 average rating, 231 reviews

A wooden table set for dining overlooks a serene lake. Glassware and plates filled with food are arranged on the table, while white chairs offer seating. Lush greenery lines the shore, complementing the calm water and bright sky.

Cottage in Ledyard

Waterfront cottage overhanging the water!

4.93 out of 5 average rating, 262 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!

4.98 out of 5 average rating, 164 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

4.88 out of 5 average rating, 101 reviews

Home in Westerly

5BR: Swim Spa, Pool Table, BBQ - Elegant Modern

4.96 out of 5 average rating, 131 reviews

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

Unobstructed Water Views & Huge Patio with Hot Tub

Family- and pet-friendly home rentals

Vacation home in New London

A scenic view captures a shoreline with sandy beaches and a calm sea. Lighthouse structures are visible in the distance against a backdrop of fluffy clouds. A person walks along the water's edge, while boats can be seen dotting the water.

4.99 out of 5 average rating, 215 reviews

Modern & Cozy Beach House - Walk to Ocean Beach

4.96 out of 5 average rating, 159 reviews

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

Room with a View on Spring Pond

4.99 out of 5 average rating, 105 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!

4.85 out of 5 average rating, 164 reviews

A bright living area is furnished with a vibrant yellow sofa and a round coffee table. Two windows allow natural light to fill the space, and a potted plant adds a touch of greenery. A piece of framed artwork is displayed on the wall.

Apartment in Mystic

Downtown Mystic, Private Deluxe 2BR + Parking - 4B

4.93 out of 5 average rating, 209 reviews

A modern kitchen features white cabinetry and granite countertops, equipped with a refrigerator, microwave, and stove. A small dining table is set with white chairs, and a potted plant adds a fresh touch. Natural light enters through a nearby window.

Guest suite in Brooklyn

Affordable In-Law Apartment in Brooklyn, CT

4.93 out of 5 average rating, 118 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

4.9 out of 5 average rating, 191 reviews

An open living area features a blue sectional sofa positioned near a wooden coffee table. Natural light brightens the space from windows above the kitchen, where bar stools line the counter. A ceiling fan and decorative artwork accent the high ceilings.

Home in Charlestown

Spacious RI Beach Escape

4.99 out of 5 average rating, 119 reviews

A comfortable living room features a light-colored sofa adorned with decorative pillows and a rustic coffee table. A large TV is mounted on the wall, accompanied by wall decor and a door leading outside. A ceiling fan hangs above, contributing to the airy environment.

Home in South Kingstown

Simple Cottage-5 minutes beach + pet friendly

Family-friendly home rentals with a pool

Superhost

Aerial view of a spacious home surrounded by lush greenery, showcasing a large pool with a deck. Solar panels are visible on the roof. The property is set in a serene wooded area, providing a sense of privacy and tranquility.

Home in Stonington

4.86 out of 5 average rating, 126 reviews

Homestead Near Mystic, Casinos & Beaches

4.91 out of 5 average rating, 197 reviews

The exterior of a Cape Cod style beach house is captured at sunset, showcasing a spacious upper balcony with an umbrella and illuminated railings. The warm hues of the sky enhance the inviting atmosphere of the home, while surrounding trees add to the serene setting.

Home in New London

Sunset Oasis 1 @ Ocean Beach: $1Mil View 6 Queen

4.99 out of 5 average rating, 102 reviews

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

Home in The Hamptons

3 BR/Pool. Walk to Beach & Town!

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

4.92 out of 5 average rating, 196 reviews

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

4.91 out of 5 average rating, 626 reviews

The exterior of a cottage is presented, featuring natural wood siding and a gabled roof. A solid front door is centered, with a small overhang extending above. A stone pathway leads to the entrance, framed by well-maintained landscaping and grass.

Cottage in The Hamptons

Montauk Oceanview

Superhost

A rustic cabin with a stone chimney is set against a backdrop of lush trees and a warm sunset. The wraparound porch features wooden railings and is complemented by neatly landscaped areas. A stone wall borders the driveway, leading to the cabin's entrance.

Cabin in Glocester

4.88 out of 5 average rating, 116 reviews

Get comfy in the country!