Vacation Rentals By Owner In Old Saybrook, CT

One floor, 1200 square feet on a 1/2 acre on a quiet residential street. Convenient to the beach, great walks, close to Dairy Queen, Mexican, Thai and Italian Restaurant. Bedroom 1 has king bed, bedroom 2 has 2 new twins and bedroom 3 has Queen and 1/2 bath. Backyard has grill . Large dining area, brand new kitchen, flat screen TV and wifi. Convenient to I-95 and Rt 9 and the train. Half way between the Coast Guard Academy and Yale. Fenced In backyard. Central air conditioning.

Great family home, fenced in back yard and Weber grill.

Old Saybrook, Connecticut, United States

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Exceptional(7)

$445.63

Remodeled 3 bedroom, 1.5 bath beach home nestled in Old Saybrook, CT. Sits on a private 1/2 acre. Just step outside and sit on the patio and listen as birds fill the air with the most tranquil sounds. Tons of wildlife. On any given day you may see all kinds of birds, chipmunks, squirrels, rabbits, deer, wild turkeys. An eagle soaring overhead or egrets playing in the marsh. Sunsets can be seen from the house and backyard. Always a beautiful end to the day. brbrThe house features a master bedroom with a queen bed and 1/2 bath. Another queen bedroom with a small desk, chair and printer. The third bedroom has two twin beds and two additional bean bag chairs for relaxing. There is one full bathroom with tub. Central air and WiFi provided. (Please note the living room fireplace is seasonal. It’s unavailable for use from May to September.)brbrThe outdoor space is very private with a gas grill and table for six. There is an outdoor fire pit with six adult Adirondack chairs and 3 kids, for those nights you are craving a s’more! There is also an outdoor shower.brbrThe property is a short bike ride to Cornfield Point beach (about a 1/2 mile) or just minutes away by car to Harvey's beach. You can apply for a Part-Time Renter beach pass for Harvey's beach by visiting the Old Saybrook Parks and Recreation website/Beach Pass Regulations. The Cornfield Point community is golf cart friendly. Golf carts can be rented from Hawkes Golf Vehicles in Clinton, CT. They do deliver/pick up the vehicle. brbrThe area is great for walking or running. Take a trip down Maple Avenue towards Fenwick and you will not be disappointed with the views. Lighthouses can be seen in the distance along this path.brbrBeach chairs, towels, toys, umbrella, beach cart and bikes provided. Nothing to do but pack your bags!brbr(Full disclosure: Exterior cameras for security purposes. Owner has a cat at house on occasion.)brbrOld Saybrook is a quaint town with lots of restaurants, shops, and beaches. It’s a great location for families, couples or a girls trip. If you are looking to retreat to a peaceful location with the most magnificent views, this is the place to be!brbrGreat place to stay if you are attending a wedding at the Saybrook Point Resort and Marina. About a 6 minute drive.

Tranquil property, amazing sunsets!

Old Saybrook, Connecticut, United States

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Exceptional(2)

$267.38

Explore the shoreline in this quaint 1920'2 Sears Kit house. Walk to South Cove at the end of the street for beautiful sunrises and wildlife viewing, or drop you paddleboard/kayak in for more adventure. Town beach and Main Street are a mile away, a nice stroll, drive or bike ride away from restaurants, shops, and The Katherine Hepburn Cultural Center/theater. We're happy to assist with any questions while you stay at our cottage.

Charming 1920's no frills cottage in peaceful Old Saybrook

Old Saybrook, Connecticut, United States

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Exceptional(16)

$425.52

Enjoy spectacular sunsets from the deck of our Marsh Side home located in beautiful Old Saybrook, Connecticut or watch the sun rise over the marsh from the front door. Our quiet family-oriented neighborhood is perfect for a relaxing getaway with loved ones, and two public beaches are a short bike ride away. There is ample space with 3 bedrooms, 2 full bathrooms and an office suitable for when work calls. Our den is the perfect hang out area after a day of exploring. Come and enjoy! Full disclosure * exterior cameras in front of home for security purposes.

Marsh View Home!

Old Saybrook, Connecticut, United States

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Exceptional(20)

Select Dates for Price

This cozy Knollwood Beach home has 3 bedroom, plus a LR open up couches that sleep 2 in the family room, 2 full baths - is available for rental (INQUIRE w/email for discounted month or longer rentals).It was completely remodeled 7 years ago and is equipped with a full kitchen and modern appliances. It is a short distance from Fenwick Golf Course and there is a golf cart to use in the area and at the golf course during your stay. It includes AC, W/D, dishwasher, patio, gas grill, exterior wood fire pit, & parking for 4 cars. Neighborhood also has a park which includes a basketball court, tennis court, playground, and baseball field. There is also a town small boat launching area a short distance from the house for kayaks and small boats on the South Cove of the CT River with access to LI Sound. This home is excellent for beach stays and stays involving events at the Saybrook Point Inn, Water's Edge Resort, and the Elks Lodge in Westbrook, CT. It is also within 30 minutes of Yale U, Wesleyan U, the Coast Guard Academy, and Connecticut College. The Katherine Hepburn Cultural Arts center and Fenwick Golf Course are a short distance from the property; it hosts wonderful concerts and programs. There are several local attractions including a seasonal Old Saybrook Mini Golf Course, Essex Steam Train, the Griswold Inn, CT River Museum in Essex, Shopping Malls Westbrook, Clinton, and Waterford. The scenery in the are is spectacular!

All year beach home. Inquire about an academic rental starting September 5th .

Old Saybrook, Connecticut, United States

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Exceptional(3)

$452

A perfect getaway! This unique, meticulously maintained rental boasts an open floor plan, hardwood floors throughout, the updated kitchen features stainless steel appliances and granite countertops, Bright and airy living room features a gas fireplace, cable tv and plenty of space for relaxing, 2 spacious private bedrooms, A full bath with a shower and jetted tub and a downstairs half bath, enjoy the serenity of a private patio perfect for relaxing and enjoying the beautiful grounds, walking distance to The Preserve perfect for hiking, mountain biking. Plenty of parking. A short drive or bike ride to the Old Saybrook town beaches, Main Street shops, restaurants, The Kate Cultural Arts Center, Fenwick Golf Course and Saybrook Point. Just a few hours by car or train from NYC and Boston. Your private shoreline retreat awaits you! Please note, the 2 bedroom unit is an in-law suite that is attached to our main house. Totally private with locked doors and your own outside access.

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

Old Saybrook, Connecticut, United States

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Exceptional(140)

$238.5

Charming, one bedroom cottage is located on historic Saybrook Point where the Connecticut River meets Long Island Sound. This fully furnished, very comfortable house with rustic yet refined decor features one bedroom, one bath, living room, and a fully-equipped eat-in kitchen. It also has SmartTV, Wifi, and air conditioning. We provide linens and towels for you!brbrAt the Saybrook Point Cottage, we are the business of hospitality. In addition to our strict housekeeping protocols, we also offer Contactless Check In/Check Out. Rest assured that we are doing everything, and then some, to ensure the health and safety of all our guests and to make your stay as comfortable and enjoyable as possible!brbrSituated on a quiet street that ends at Saybrook's South Cove, there are sliding glass doors that open onto a beautifully landscaped, private park-like lawn. There is no swimming in South Cove, so it's just a five minute drive to the sandy Town Beach. The bright and airy guest house is ideal for singles or couples looking for relaxation and adventures. brbrMAXIMUM OCCUPANCY: TWO PERSONS.brbrPET FRIENDLY- Bring your pets!! Please note the property is not fenced in.brbrSometimes you need a quick change of scenery to break the cycle! brbrLocated less than a two hour drive from mid-town Manhattan and Boston, there is also an Amtrak stop in town.brWalk to the water or into the village. brEnjoy the views from the deck or barbeque with the gas grill. brThe area is perfect for long walks, bicycling, scenic drives, canoeing, kayaking, antiquing, and more. brbr30 minutes to Mohegan Sun and Foxwoods br20 minutes to Mystic Seaport and Aquarium br15 minutes to the Goodspeed Opera House and Outlet Malls brOne-quarter mile to the Saybrook Point Spa and Fitness CenterbrbrAvailable year round. See summer rates below. br2night minimum off- season. brSaturday-Saturday minimum from Memorial Day-Labor DaybrLonger stays are negotiable. Contact owner for additional information and photos.brbrFeel free to contact owner with any questions .brbrKeywords: House, Cottage, Getaway, Bungalow, Love Shack, Weekend Retreat

Saybrook Point Cottage - Charming and Private

Old Saybrook, Connecticut, United States

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Exceptional(1)

$2875.0

The home sits right on the Long Island Sound, with stunning views of the water. Nine bedrooms, new kitchen (with two refrigerators, two ovens, large stove, wine fridge and all modern appliances), full gym with Tonal, Woodway, Precor and free weights. Central HVAC, Apple TV with all streaming services, two new 75 TVs, central vacuum, barbecue grill, finished basement with a game room filled with kids’ toys. Big yard for family sports as well as a community playground, nine hole golf course, four clay tennis courts, sailing, swimming, kayaking and biking. Peaceful, tranquil and beautiful getaway for a family.brbrNo parties or events allowed. Strictly for family vacations. The community takes this very seriously.

Stunning Seascape Home For A Dream Family Holiday

Old Saybrook, Connecticut, United States

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Exceptional(8)

$657.28

Escape to this lovely house in picturesque Old Saybrook. With 3 bedrooms including a king, queen, and twin with trundle bed, guests will find comfort and space to unwind. Enjoy the enchanting, jetted bathtub in one of the 2 bathrooms. The family room offers a large screen Smart TV, and an additional cozy space with a sofa bed for extra guests. Large eat in kitchen with all the amenities. Living room with bar area for adult entertainment. comfortable outdoor living with front and rear seating areas, dining area, grill, fire pit and outdoor shower. Plenty of off-street parking. Private beaches and playgrounds all within walking distance. Everything needed for a day at the beach is included so just bring your suit and flipflops. Our place is fully equipped for both long or short stays to make your holiday one to remember.

Charming year-round beach home in Indian Town, Old Saybrook

Old Saybrook, Connecticut, United States

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Exceptional(5)

$539.91

This tired little cottage needed some TLC. We bring it to you and your family in fully renovated condition. Two bedrooms with extra office/sunroom for additional guests. A stone’s throw from Cornfield Point Association and rocky beach.brbrBoat ramp ocean access available to guests. Home has adequate driveway parking for trailer. brbrUse of Cornfield Point Association clubhouse yard, tennis court, basketball court, included for guests, and private association beach, of course!

Fully Updated Cornfield Point Beach House, Old Saybrook, CT

Old Saybrook, Connecticut, United States

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Exceptional(13)

$614.1

*****SEASTAR******brbrEnjoy the beauty and Seascape of Knollwood Beach located in beautiful and scenic Old Saybrook Connecticut . Just a few minute walk to the Private beach and private Amenities . The Beach house comfortably sleeps four people with an outdoor and indoor shower. Facilities include Air-conditioned and electric baseboard heating year-round home . full Kitchen, full bathroom, microwave, dishwasher , tennis courts, basketball court and playscape amenities. Our cozy Seascape is nestled on a beautiful marsh bursting with natures scenery . Plenty of outdoor patio seating with umbrella and smore's firepit available for use. brbr Wi-Fi and cable TV with HBO for viewing. . Bed linens, bath towels, and pillows are available for your use or you may bring your own. Spa bath and shower amenities Keurig coffee machine and fresh coffee for your morning Joe are available! Immerse yourself in the ambiance of our marsh side setting under the twinkling stars with our outdoor moonlit lights.brPlease bring your own beach towel. Come stick your toes in the sand and relax with the tranquility of Old Saybrook . June 1st thru Sept. 1st requires a two night minimum stay. We look forward to your stay!

SeaStar Beach House Scenic Salt Marsh View Close Walk To Ocean

Old Saybrook, Connecticut, United States

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$674.39

Welcome to this year round coastal sanctuary! This stylish home is perfectly positioned within the charming Knollwood Beach community. Just a block away you’ll discover the clubhouse, pickleball/tennis courts and playground. A mere 2 blocks separate you from your private beach!brbrStepping inside, you’re welcomed by an atmosphere of complete comfort. House has been updated and refreshed with all new furniture. Location is close to all local attractions in Old Saybrook including the historical Fenwick golf course.brbrJust bring your beach attire, sit back and relax!!

The Beach life at Knollwood beach , Year round house short walk to the beach

Old Saybrook, Connecticut, United States

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$335.14

Welcome to this charming waterfront cottage in Old Saybrook. This nice one-bedroom retreat offers guests a cozy bedroom and living room with sliders to the deck with an incredible view of the marina. Watch the boats sail by as you eat on the lovely deck or relax on the private sand beach. Great for adults looking for one level living and a relaxing atmosphere, as well as small family looking for beach fun. The living room has a queen pull out sofa and a twin pull out sofa. Wake up to the sunrise with coffee on the small grassy lawn or sandy beach. Use the outdoor shower after a day of fun at the beach. All amenities of Indiantown Beach Association available to renters, including two private beaches, playground and basketball court. 2 paddleboards, kayaks and bicycles available to guests.

Charming waterfront cottage in Indiantown Old Saybrook

Old Saybrook, Connecticut, United States

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Exceptional(7)

$603.75

Direct oceanfront - pure paradise at the beach! Spectacular views of Long Island Sound with a large, partially covered, patio and private steps to the water/sand. Master bedroom with a wall of windows facing the water...wake up each morning to magnificent views. A slider to the waterside patio connects indoor and outdoor living. Dine alfresco, listen to the sound of the waves, watch the sunset - it is truly magnificent as the sun fades into the horizon and the sky illuminates with color.

Waterfront oasis 4 bdr house in Old Saybrook direct waterfront amazing sunsets

Old Saybrook, Connecticut, United States

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$467.36

Discover the perfect blend of privacy, breathtaking natural beauty, and effortless charm at this spacious 4-bedroom waterfront home in Old Saybrook, Connecticut. Nestled along the majestic Connecticut River, this inviting property offers sweeping, unobstructed views that will captivate you from the moment you arrive.brbrWake up each morning to golden sunrises painting the river in vibrant hues, while sailboats glide gracefully by and an orchestra of birds fills the air with song. Whether you're sipping coffee on the deck, watching ospreys soar overhead, or simply soaking in the peaceful surroundings, the riverfront setting delivers a front-row seat to nature’s most spectacular show. The home sits on a private, serene lot where you can truly unplug and reconnect—with family, friends, or just yourself.brbrInside & Out – Designed for Relaxation & CelebrationbrThis well-appointed 4-bedroom home comfortably sleeps up to 8 and flows beautifully for both quiet getaways and lively gatherings. Gather in the expansive living areas or step outside to the generous outdoor spaces perfect for entertaining. Fire up the grill, enjoy al fresco dining with river views, or unwind around a fire pit as the stars emerge. The home’s thoughtful layout and comfortable furnishings make it ideal for multi-generational family vacations, friend reunions, or romantic escapes.brbrLocated just 1.5 miles from the heart of charming downtown Essex, Old Saybrook, and Old Lyme, you’re perfectly positioned to enjoy the best of the Connecticut shoreline. Minutes to waterfront parks, boutique shops, acclaimed restaurants, and historic sites. Miles of scenic walking and biking paths are right nearby, and hiking trails through pristine woodlands are just minutes away. Whether you want a day of boating, kayaking, beachcombing at nearby coves, or simply wandering the picturesque villages, everything you need is conveniently close.brThis is more than a vacation rental—it’s a memorable Connecticut River experience that guests can return to year after year. Book your stay and create lasting memories surrounded by stunning views, abundant wildlife, and the timeless charm of coastal Connecticut.brReserve your riverfront escape today—dates fill quickly!br(Perfect for families, couples, friends, and multi-generational groups seeking privacy, nature, and proximity to New England’s most beloved shoreline towns.)

Breath taking water views from this 4-bedroom Home in Old Saybrook.

Old Saybrook, Connecticut, United States

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Exceptional(7)

$503.13

Come stay at this tastefully updated 4 bedroom-2.5 bath home. Large kitchen and spacious rooms. Each room has its own TV and climate control. Remodeled bathrooms. Situated just minutes from beaches, shops, restaurants, and marinas this is the perfect place to call home for your getaway. 1.1 miles from Saybrook Point Inn. Walk or bike into town (.5 miles). Views of South Cove. 1.8 miles to Town Beach (beach parking pass provided). 3 floors of living space. Backyard use for entertaining or soaking up the sun. Grill, Outdoor shower, beach supplies, bikes all included! Sleeps 12!brbr3 King bedsbr1 Queen bedbr2 day beds with trundlesbr

Beautiful Cottage Cove!

Old Saybrook, Connecticut, United States

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Exceptional(3)

$656.2

Consider this house your home away from home while you visit Old Saybrook. This serene property boasts 3 bedrooms, including 2 king beds and 3 twin beds, perfect for a family or group of friends. With 4 bathrooms featuring a shower and jetted bathtub, guests will have plenty of space to relax and unwind. Enjoy the tremendous fitness room, AC, WiFi, and more during your stay. Our place will help you feel at home while you're traveling in Old Saybrook.

Direct Waterfront -Charming 3-BR house with AC, fitness room in Old Saybrook

Old Saybrook, Connecticut, United States

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Exceptional(45)

$609.5

beautiful beautiful private beach-knollwood beach old saybrook,brso much to do in the areabrthree bedroom, one bathroom adorable ranch,brone short block to beach-enjoy long island sound, bring you bikes -stroll through a charming neighborhoodbrtennis court, basketball court, playground-just at corner of streetbrnothing to want for just grab your towel and sunscreen and have some funbrcome back and enjoy cable tv/central air and pop in a movie/read a book, make a mealbrbrNO garage entrybrGuest must bring their own sheets, queen, queen, full on full bunkbrCameras outside of house for safety and to ensure no additional guests brbrIt’s not allowed only brGuests on reservationbrbr

adorable ranch in beach community

Old Saybrook, Connecticut, United States

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Exceptional(2)

$328.29