
Family-friendly vacation rentals in Old Saybrook
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Old Saybrook

Total vacation rentals
Explore 110 vacation rentals in Old Saybrook

Nightly prices starting at
Old Saybrook vacation rentals start at G$10,441 GYD per night before taxes and fees

Verified guest reviews
Over 3,150 verified reviews to help you choose

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
110 of Old Saybrook vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Old Saybrook rentals

4.9 Average rating
Old Saybrook stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Old Saybrook
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

"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.

Year Round Beach House in Old Saybrook, CT.- Pets
Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Steps to Beach! *Cozy Cottage* Pet Friendly
Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

Beautiful View Cottage
Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
Explore our Old Saybrook retreat on Great Hammock Rd, a cozy spot near the beach. Perfect for romance or family fun, it boasts stunning views and amenities. Relax in the hot tub, use bikes for local exploration, and enjoy evenings by the fire pit. Indoors, a fireplace adds warmth. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook! Please note Our property is strictly an animal-free zone due to severe allergies persisting in the family.

Historic Hearthstone Cottage
Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

The Cottage
Step into a piece of history with this charming, fully converted 1930s changing house. Ideally located, it’s just a short stroll to downtown or a scenic bike ride to the beach, putting the best of the area right at your doorstep. Inside, you’ll discover a thoughtfully designed studio layout, offering the perfect setting for a peaceful getaway. The Cottage seamlessly blends comfort, convenience, and character, creating a truly inviting retreat.

Best of both worlds!
Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

Your Nest Near The Beach
Welcome to A Shore Thing, a retro modern beach cottage. This bright and cheerful escape is perfectly located for exploring the shoreline. Whether you are visiting in the summer for sun, surf and sand or in the quieter off-season, you will find the shoreline is packed with an incredible array of inviting destinations. The cottage is just 3/4 of a mile from the beautiful private sandy beach.

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!

Cozy Loft Getaway
Our private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

Adorable Beach House on LI Sound
Beach House with incredible views of the Thimble Islands - 4 min walk to Restaurants including Lenny’s, Zagat award winner for fresh local seafood - 1 min walk to Bud’s Fish Market - 3 min walk to Indian Neck Liquor - 3 min drive to brewery w/ food trucks & music - 4 min drive to Branford Green w/ specialty stores, coffee & ice cream
Popular amenities for Old Saybrook family-friendly rentals
Family-friendly home rentals with a hot tub

Breathtaking home with unforgettable views & pool!

Waterfront cottage overhanging the water!

Luxury cottage by the sea with hot tub and pool

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

Cozy cottage 5 minutes from UConn

Luxe Bolton Lake

Romantic Getaway at The Lake!

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos
Family- and pet-friendly home rentals

Water Forest Retreat -Octagon

Insta-worthy * Couples Retreat

Pet Friendly Bungalow!!!

Unique apartment in former art gallery.

The Dragon Fly Garden

Shalom Cottage Private Beach Access

@Get_Yurty w/ 2 sleeping pods, NO Cleaning/Pet fee

"Amanita" Tiny Cabin on Beach Pond Shore w/Sauna
Family-friendly home rentals with a pool

Cozy private apt 8 mins from UCONN - solar powered

3 BR/Pool. Walk to Beach & Town!

Romantic Spa Retreat minutes to Mohegan Sun Casino

Ocean View Studio with King Bed

Serene w/ large pool ~1 block to waterfront dining

Peaceful Oasis steps from Mohegan Sun

Secluded Farmhouse - Studio Apartment Style Unit

Explore the Water & Woods at a Relaxing Retreat
When is the best time to visit Old Saybrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$68,910 GYD | G$64,943 GYD | G$65,151 GYD | G$73,086 GYD | G$82,483 GYD | G$85,824 GYD | G$82,483 GYD | G$82,483 GYD | G$72,878 GYD | G$67,866 GYD | G$63,898 GYD | G$65,987 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
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