
Holiday rentals with outdoor seating in Old Saybrook
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Old Saybrook
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

New! “LaBoDee”
“LaBoDee”, a fun play on the word abode, house, is a tiny cottage located central to CT’s unique shoreline communities, just off I95. “LaBoDee” is one room with a fully equipped kitchenette, ready for those who would like to stay awhile. “LaBoDee” is on a property contiguous to a state forest (a trail is right outside the door) yet within walking distance is a delicious deli, market, gas station, pizza, a lake, and close by is the beach. A local restaurant has day passes for their beach- $20!!

Unique apartment in former art gallery.
The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. One bedroom on the ground floor with full bath nearby. The other bedroom is in the loft with queen bed with a daybed in the sitting area for two extra guests. We gladly welcome clean, well behaved pets. ($50 pet fee) Pet sitting and dog walking available for an additional fee. On site babysitting also available.

Peaceful Riverfront Cottage w/Dock, Walk to Beach
This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

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!

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.

Lakefront Retreat Tiny House
Discover a tranquil lakeside escape in our cozy tiny house, nestled within a boutique RV Park in East Lyme, CT, just 15 minutes from Mystic. Perfect for couples seeking a romantic getaway or individuals looking for a serene retreat. Compact in size but loaded with all the comforts you need: a comfy queen bed, smart TV and fast WiFi, a fully-equipped kitchen, a bathroom with full sized shower and flushing toilet, inviting decor and an unbeatable lake view!

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.

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!

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.

The Dacha at the Mystic Farmhouse
A Historic Artist’s Retreat Near Downtown Mystic Lovingly known as The Dacha for nearly 80 years, this one-of-a-kind gem was built in 1945 as a studio for the artist who once called the property home. Fully insulated for cozy winter stays, the unique structure is tucked away on a peaceful piece of land, just five minutes from downtown Mystic.
Popular amenities for outdoor seating rentals in Old Saybrook
House rentals with outdoor seating

Stunning Artisan Waterfall Escape, Walk Downtown

Luxury Stay in Expansive Historical Home

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

Year Round Beach House in Old Saybrook, CT.- Pets

Cozy Comforts!

Beachfront Paradise

Exclusive Sag Harbor Compound

Silver House: 3BR Home with Private Beach Access
Apartment rentals with outdoor seating

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Luxury 3 Bedroom Apt Near Mystic Drawbridge

Mystical Ocean View in Historic Stonington Borough

The Whaler’s Loft · Ocean Beach, Mystic & USCGA

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

The Millhouse Downtown Chester

Retreat in New Haven by Stephanie and Damian

Spacious Cozy Guest Suite
Apartment rentals with outdoor seating

2 BR Waterfront Autumn Escape in Wine Country

Montauk Waterfront Condo w/ Sunset Views

Beautiful Waterview Condo on the North Fork of LI

The Vacay Villa

Peaceful Oasis steps from Mohegan Sun

Beach Escape. Walk to Beautiful Beaches

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

Near Casino-Heated Pool/Jacuzzi/Sauna- Onsite Spa
When is the best time to visit Old Saybrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $316 SGD | $318 SGD | $316 SGD | $350 SGD | $381 SGD | $418 SGD | $423 SGD | $441 SGD | $385 SGD | $350 SGD | $356 SGD | $354 SGD |
| 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 with outdoor seating in Old Saybrook

Total holiday rentals
Explore 80 holiday rentals in Old Saybrook

Nightly prices starting at
Old Saybrook holiday rentals start at $139 SGD per night before taxes and fees

Verified guest reviews
Over 3,330 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
80 of Old Saybrook holiday rentals include wifi 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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- Rentals with outdoor seating Connecticut
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- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Mohegan Sun
- East Matunuck State Beach
- Long Island Aquarium
- Hammonasset Beach State Park
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- Burlingame State Park
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