
Family-friendly holiday rentals in Old Saybrook
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Old Saybrook
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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

The Millhouse Downtown Chester
An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

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.

Peaceful Oceanfront Cottage
Welcome to our oceanfront guesthouse. Enjoy the waterfront view as our guests on this beautiful private family compound. A modernized quintessential 18th century get-away. The entire cottage is yours, with 2 bedrooms, 1.5 bathrooms, full kitchen, patio with picnic table, living room and sunroom all offering stunning views of the water and evening sunsets. Just a short walk to a sand bar (great for walking and kids) and near multiple beaches. A very quiet and safe neighborhood .

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Storybook 2 Bedroom Cottage
Enjoy a relaxing stay at this charming storybook home which has just been refreshed professionally and redesigned with unique and gorgeous antique furnishings and decor. Built in 1895, the home was re-envisioned by designer Charles Spada in the 90’s. A lovely private back yard with beautiful stone work and plantings. The proximity to shopping, galleries, restaurants and Old Saybrook, Town Beach and Katherine Hepburn theater makes this location ideal.

1920’s charming dollhouse near South Cove
Simple, no frills guest cottage near South Cove in Old Saybrook. Drop your kayak /paddle board in at the end of the street, walk to town for dinner or a show at the Katherine Hepburn Theater, or enjoy a day at town beach only 1.5 miles away. This is a shabby chic escape in a friendly, quiet neighborhood. A few quirks but tons of charm! If you are looking to unplug and sit by the fire pit, read a book, and go to the beach, this is the place 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.

River Barn, Sidewalk Stroll into Essex Village
The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

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!

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!
Popular amenities for Old Saybrook family-friendly rentals
Family-friendly home rentals with a hot tub

Breathtaking home with unforgettable views & pool!

Romantic Getaway at The Lake!

Oceanfront Beach House w/ Private Hot Tub

Creekside Cabin with Wood Fired Hot Tub & Firepit

Beach Haven - waterfront, near Yale, sunsets

Two floor Norwich Spa Villa near Mohegan Sun

Casino Stay & Play House w/Hot Tub, Game Room

The Red Cabin-Secluded Getaway with backyard Brook
Family- and pet-friendly home rentals

Modern & Cozy Beach House - Walk to Ocean Beach

Water Forest Retreat -Octagon

Savor Ocean Sunsets at a Soothing Beachfront Haven

Salty Breeze - Waterfront Cottage on the Cove

Town's End Farm

Charm + location. Walk to beach, town, & harbor.

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Walk to the beach at Black Point, Niantic, Ct
Family-friendly home rentals with a pool

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

FREE Private Indoor Heated Pool - Mystic Home

Montauk Waterfront Condo w/ Sunset Views

The Quail’s Nest

Cheerful East Hampton home with Pool

Private Cozy Cottage with Pool / Private Beach

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Modern Southampton Cottage | Heated Pool & Peloton
When is the best time to visit Old Saybrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $502 AUD | $442 AUD | $431 AUD | $455 AUD | $501 AUD | $561 AUD | $567 AUD | $567 AUD | $501 AUD | $466 AUD | $439 AUD | $453 AUD |
| 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 |
Quick stats about holiday rentals that are family-friendly in Old Saybrook

Total holiday rentals
Explore 90 holiday rentals in Old Saybrook

Nightly prices starting at
Old Saybrook holiday rentals start at $100 AUD per night before taxes and fees

Verified guest reviews
Over 2,990 verified reviews to help you choose

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Old Saybrook holiday 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!
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- Family-friendly rentals Connecticut
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- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
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- Mohegan Sun
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