Family-friendly vacation rentals in Stonington

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.

"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.

4.99 out of 5 average rating, 255 reviews

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.

4.97 out of 5 average rating, 264 reviews

Perfect New England Getaway has a pool/ hot tub

Welcome to a 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.

4.99 out of 5 average rating, 261 reviews

Guesthouse in Stonington

Historic Mystic Cottage w/ Fire Pit & King Bed

Transport yourself to Mystic's shipbuilding heyday at Smith Cottage. This adorable, open-concept, pet-friendly, two-bedroom retreat in historic Old Mystic captures the essence of a bygone era. Nestled at the head of the Mystic River, it offers a perfect base for exploring the coastline and Mystic Seaport. With Colonial nautical charm and 21st-century comfort, the Smith Cottage invites you to experience genuine New England hospitality. Your journey into Mystic's maritime history begins here!

A spacious home is set within a wooded area, surrounded by tall trees and a manicured lawn. A signpost indicating the trails is visible in the foreground, adding to the serene atmosphere of the property.

4.99 out of 5 average rating, 136 reviews

Grand Hide-A-Way Central to Mystic and Vineyards

*This is not a party house and we do not accommodate parties or bacheloer/bachelorette events of any kind. Forget your worries in this spacious and serene retreat. One level living with four bedrooms and two full bathrooms on the first floor. The finished basement offers additional entertainment and sleeping space, a full bathroom, and a walk-out to the hot-tub. Wifi, central air, a DVD player, and Smart TVs for your indoor enjoyment. Outdoor fire pit, dining area, and private hiking trails.

4.94 out of 5 average rating, 348 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

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!

4.99 out of 5 average rating, 204 reviews

An open great room features a large sectional couch facing a wall-mounted TV. A dining table with four wooden chairs is visible, while additional seating is arranged nearby. Natural light streams in through multiple windows with plantation shutters, highlighting the clean, minimalist design.

Home in Mystic

Steps from downtown & Seaport

Stay in downtown Mystic, footsteps from all the restaurants, shops & sights! Leave the cars behind in our 3 car driveway. Relax in the open great room 1st floor with a large couch, 65” HD Smart TV! Full kitchen and dining area seating. Laundry on 1st with 1/2 bath and full sleeper sofa. 2nd FL has 1800's charm with cathedral ceilings, 2 Queen bedrooms, and bath w/shower - Linens provided. Step outside to a private fenced in yard w/BBQ grill, w/ outdoor seating and dining or play cornhole

5.0 out of 5 average rating, 126 reviews

An open-concept kitchen and living area is captured, featuring modern stainless steel appliances and white cabinetry. A spacious island with bar stools offers additional seating. Natural light fills the space through multiple windows, highlighting the cozy living area with a coffee table and comfortable seating.

Apartment in Mystic

Luxury 3 Bedroom Apt Near Mystic Drawbridge

Experience the energy of downtown Mystic by staying in this newly remodeled & spacious top 2 floors apt. that is a 5 minute walk to the Mystic waterfront/drawbridge, S&P Oyster Co., SIFT, Mystic Pizza, & much more! Furnished Apt Details: - Naturally sunlit rooms & modern furniture - Living room, dining room, & kitchen: open concept - 3 Bedrooms: 2 queen & 2 twin beds - 1 bathroom with spacious shower, modern vanity & stackable washer & dryer - Access to backyard with patio & BBQ to unwind

An outdoor dining area is situated in the yard, featuring a large table surrounded by white chairs, shaded by a yellow canopy. A grill is positioned nearby on a sandy patio, with greenery and a two-story house visible in the background.

4.99 out of 5 average rating, 132 reviews

New Stonington Waterfront

Beautiful new five bedroom, four bath waterfront home on Wequetequock Cove in Stonington, built in 2021. Water views from the house and backyard patio, with outdoor dining area and fire pit. Sandy Point, Napatree Beach, East Beach Watch Hill and Dubois Beach are all accessible by car or boat. Paddle to Saltwater Farm Vineyard up the Cove, or explore Barn Island Nature Preserve. Just minutes from Stonington Borough, Downtown Mystic, Mystic Seaport, Mystic Aquarium, Westerly and Watch Hill.

4.9 out of 5 average rating, 166 reviews

A bright living area features a comfortable white sofa and a modern armchair beside a wooden side table. Natural light floods the room through multiple windows, enhancing the neutral color palette and showcasing the sliding barn doors leading to additional spaces.

Condo in Mystic

Harper House Heart of DT Mystic Luxury Getaway

Historic Downtown Mystic. This immaculate designed retreat is professionally managed and offers an enjoyable winter stay. Just steps to Deep Water Marinas, Fine Restaurants including Captain Daniel Packer Inn, SIFT Bakery, Train Station, and Unique Shops. This modern apartment features a fully equipped high-end kitchen with a microwave, blender, toaster, cooking essentials, and a Keurig machine. 1 on-site parking space and a shared common backyard space if available for your enjoyment.

4.88 out of 5 average rating, 112 reviews

A charming multi-story house features a combination of wooden shingles and trimmed details. A welcoming front porch with white railings is complemented by multiple windows that bring natural light into the space. Nearby trees add greenery to the cozy neighborhood setting.

Apartment in Stonington

Charming apartment in heart of Stonington Borough

Located in the heart of idyllic Stonington Village, this apartment is blocks away from stores, restaurants, coffee shops, and library. Main bedroom has a king size bed; second room can be used as an extra bedroom (twin bed) or as a study. Large living/dining area looks out to front porch, where you can enjoy a cup of coffee or a meal. Pots, pans, silverware, sink, stove/oven, and refrigerator can be found in the kitchenette. Towels and sheets are provided; walk-in shower in bath.

The indoor heated pool features a bright blue expanse of water inviting for a refreshing swim. Comfortable lounge seating is positioned nearby, and a bar area provides space for poolside refreshments. Large sliding glass doors bring in natural light and offer views of the serene outdoor setting.

4.99 out of 5 average rating, 147 reviews

Heated Indoor Pool • 4 King Beds • Walk Downtown

Spread out in a spacious 3,000 sq ft retreat designed for families and groups, with four king beds, three full baths, generous gathering spaces, and a private heated indoor pool you can enjoy year-round. Cook together in the large kitchen, unwind poolside or outdoors, then explore downtown shops, restaurants and attractions on foot. A comfortable home base for multigenerational trips, family weekends and group getaways.

A serene bedroom is presented with a spacious bed dressed in neutral linens and accented with patterned cushions. Two stylish nightstands with lamps flank the bed. Above the bed, framed artwork contributes a modern touch, while natural light filters through the window covered by soft curtains.

4.97 out of 5 average rating, 135 reviews

Home Away From Home - 3bdr 1 ba

Welcome to our Home Away From Home, where you will be closely located to Westerly downtown, the beach, shopping, dining, Mystic, the Casinos, and Watch Hill (which is where the beautiful Ocean House and Taylor Swifts home is located). Our home is family friendly and offers all must-have items for your littles. But even without littles, our home offers a spacious and comfortable atmosphere for all guests.

Popular amenities for Stonington family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.97 out of 5 average rating, 158 reviews

Unobstructed Water Views & Huge Patio with Hot Tub

Guest suite in Stonington

Morgan Suite - spacious | hot tub | water views!

4.98 out of 5 average rating, 401 reviews

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.

4.87 out of 5 average rating, 142 reviews

Mystic Woods Homestead | Pool, Hot Tub, Casinos

4.9 out of 5 average rating, 260 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!

4.99 out of 5 average rating, 151 reviews

A private hot tub is surrounded by a spacious backyard, illuminated by soft outdoor lighting. A wooden deck and Adirondack chairs are visible, while a fire pit sits nearby, creating an inviting outdoor space for relaxation.

Home in Mystic

NEW! Updated Mystic Home w/ Sauna, Hot Tub & Deck

4.97 out of 5 average rating, 231 reviews

The farmhouse, constructed in 1856, is showcased with its classic white exterior and black accents. Large windows allow natural light to fill the space, while lush greenery surrounds the property. A pebble pathway leads to the entrance, enhancing the inviting atmosphere.

Home in Old Lyme

Modern Farmhouse with Hot Tub in Old Lyme, CT

4.92 out of 5 average rating, 260 reviews

A serene bedroom features a spacious bed adorned with white bedding and decorative pillows. Nightstands with lamps flank the bed, and a cozy couch with patterned cushions offers additional seating. Natural light filters through sheer curtains, enhancing the calming environment.

Condo in Norwich

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf

4.92 out of 5 average rating, 134 reviews

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

Breathtaking home with unforgettable views & pool!

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 286 reviews

A charming blue cottage is framed by lush greenery, with a stone pathway leading to a welcoming front door. The porch features red chairs, inviting relaxation. The yard is expansive, dotted with various plants and trees under a clear blue sky.

Cottage in Mystic

Cottage in downtown Mystic

4.91 out of 5 average rating, 112 reviews

A bright living area features a red sofa adorned with yellow pillows, positioned beside a vibrant area rug. Natural light streams through two windows, with a potted plant adding a touch of greenery. A round coffee table is centered in the space.

Apartment in Mystic

Mystic Renovated Open Plan - Walk Everywhere - 9A

A cozy living area is furnished with a sectional sofa, accent chairs, and a small coffee table. A colorful area rug enhances the space, while natural light enters through large windows. A dining table is also visible, creating a functional area for gatherings.

4.95 out of 5 average rating, 176 reviews

Bright and Cheerful Two Bedroom Home in Mystic

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

Downtown Oasis-1 bedroom-Walk to it all-sleeps 4

4.85 out of 5 average rating, 168 reviews

4.99 out of 5 average rating, 297 reviews

Beautiful Modern Cape Downtown Mystic

4.87 out of 5 average rating, 106 reviews

A vibrant sunset casts warm hues across the water, reflecting the golden light onto moored boats in the marina. Silhouettes of trees and power lines frame the scene, while calm waters ripple gently in the foreground, creating a serene evening atmosphere.

Cottage in Stonington

Mystic Magical Sunsets awaits your arrival

4.93 out of 5 average rating, 281 reviews

A bright kitchen area is equipped with modern white cabinetry and granite countertops, providing ample space for cooking. A wooden dining table with chairs sits in the center, adorned with a vase of fresh flowers. Natural light fills the room, enhancing the clean and inviting atmosphere.

Apartment in Mystic

Stylish Downtown Mystic Apt.

4.89 out of 5 average rating, 142 reviews

A serene view of the home surrounded by lush greenery and blooming trees, reflected in the calm waters of the nearby pond. The property is framed by tall trees, creating a peaceful atmosphere in the rural setting.

Home in Hopkinton

Estate with lake near beaches & Westerly

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 175 reviews

A spacious living room is highlighted by a unique whale wall art piece and a cozy seating arrangement. A comfortable gray sofa is paired with a nautical-themed chair. Large windows allow natural light to fill the room, creating a welcoming atmosphere.

Home in New London

Beauty and the Beach!

4.91 out of 5 average rating, 154 reviews

A two-story house is framed by lush greenery and vibrant flowering shrubs. The exterior showcases a combination of brick and wood, with multiple windows allowing natural light to fill the interior. A clear blue sky with scattered clouds completes the picturesque setting.

Home in Exeter

Nature's Nook

Superhost

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

4.92 out of 5 average rating, 216 reviews

4.98 out of 5 average rating, 252 reviews

Condo in Norwich

Peaceful Oasis steps from Mohegan Sun

4.91 out of 5 average rating, 263 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

4.96 out of 5 average rating, 162 reviews

A cozy bedroom features a dark upholstered headboard with an arrangement of plush pillows. Soft lighting is provided by a bedside lamp, creating a serene ambiance. Above the bed, three art pieces depict a sun motif, adding warmth to the neutral wall color.

Home in Norwich

Cozy Condo in Norwich- Minutes from Mohegan Sun