Vacation Home Rentals By Owner In Old Saybrook, CT

Showing 20 Of 42 Vacation Rentals

$845.25

Spectacular Home with Deep Water Dock

Old Saybrook, Connecticut, United States

Beautiful cape style home with 100' of waterfront and a 25' dock. This 3 bedroom 1.5 bath home has everything needed for the perfect summer getaway to the amazing town of Old Saybrook CT. New mechanicals, new roof, new windows, newly sided, a deck with power awning to watch the sunsets over the canal. Set on the end of a very quiet street enjoy the peaceful days and nights to yourself or entertain family and guests with the beautiful backyard setting.brbrThe home has central air in each room and fans in each bedroom. There are ceiling fans on the first floor and the tv room has its own ductless mini split system with two remote units. brbrThe home doesn’t have direct walking access to any beach but is within: br25 min to Harkness Memorial State Park br25 min Bluff Point State Parkbr10 min to Rocky Neck State Parkbr22 min to Hammonasset Beach State Park brbrThe home is not part of a private beach association. An extra fee applies if you’re bringing a boat, and will be determined at the time of booking based on size and length of stay.

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Exceptional(40)

$485.1

/ Nightly

Private Vacation Home

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

Old Saybrook, Connecticut, United States

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.

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Exceptional(7)

$445.63

/ Nightly

Private Vacation Home

Tranquil property, amazing sunsets!

Old Saybrook, Connecticut, United States

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.

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Exceptional(16)

$425.52

/ Nightly

Private Vacation Home

Marsh View Home!

Old Saybrook, Connecticut, United States

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.

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Exceptional(20)

Select Dates for Price

Private Vacation Home

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

Old Saybrook, Connecticut, United States

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!

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Exceptional(8)

$657.28

/ Nightly

Private Vacation Home

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

Old Saybrook, Connecticut, United States

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.

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Exceptional(5)

$539.91

/ Nightly

Private Vacation Home

Fully Updated Cornfield Point Beach House, Old Saybrook, CT

Old Saybrook, Connecticut, United States

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!

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Exceptional(13)

$614.1

/ Nightly

Private Vacation Home

SeaStar Beach House Scenic Salt Marsh View Close Walk To Ocean

Old Saybrook, Connecticut, United States

*****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!

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$674.39

/ Nightly

Private Vacation Home

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

Old Saybrook, Connecticut, United States

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!!

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Exceptional(7)

$603.75

/ Nightly

Private Vacation Home

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

Old Saybrook, Connecticut, United States

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.

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$467.36

/ Nightly

Private Vacation Home

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

Old Saybrook, Connecticut, United States

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.)

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Exceptional(7)

$503.13

/ Nightly

Private Vacation Home

Beautiful Cottage Cove!

Old Saybrook, Connecticut, United States

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

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Exceptional(3)

$656.2

/ Nightly

Private Vacation Home

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

Old Saybrook, Connecticut, United States

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.

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Exceptional(45)

$609.5

/ Nightly

Private Vacation Home

adorable ranch in beach community

Old Saybrook, Connecticut, United States

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

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Exceptional(2)

$328.29

/ Nightly

Private Vacation Home

Quaint cottage at Cornfield Point Assn - Walk to Beach

Old Saybrook, Connecticut, United States

Quaint cottage at private Cornfield Point Beach Association, two upstairs bedrooms (queen bed and two twin beds) with one full bathroom; one downstairs bedroom (full bed) with full bathroom; kitchen with eating area; living room with Xfinity TV; Xfinity Internet; two-block walk to private beach; tennis and playground at Clubhouse available; partially fenced in backyard with patio and grille; three-season porch. Easy access to downtown Old Saybrook and Saybrook Point where you can go mini golfing; watch the boats on CT River; nearby shopping and restaurants, including Saybrook Point Inn Resort and Marina; 30 minute drive to Mohegan Sun Casino and Mystic Aquarium. Great walking area and great sunsets!

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Exceptional(2)

$645.27

/ Nightly

Private Vacation Home

Fenwood Coastal Getaway Private Beach Access

Old Saybrook, Connecticut, United States

Summary:brbrWelcome to your perfect beach getaway! This charming beach house offers everything you need for a relaxing and comfortable stay. The home comfortably sleeps 6 with 3 bedrooms, 2.5 bathrooms. You’re just a short stroll away from the Old Saybrook private Fenwood beach, where you can soak up the sun, swim, or simply relax and listen to the soothing sound of the waves.brbrbrbrThe Space:brbrPrior to your arrival, our home undergoes professional cleaning to ensure a clean and welcoming environment. We meticulously prepare and set up each space, paying close attention to detail, so that you can immediately relax and enjoy your stay from the moment you step through the door. brbr brbrWith three bedrooms, there's plenty of space for the whole family or a group of friends to unwind after a day of sun and sand. All 3 bedrooms are located on the upper level. A full bathroom with a detachable shower head is also on the upper level. Bedrooms 1 and 2 feature queen beds. Bedroom 3 boasts a king bed, tv and a private bathroom with a shower. brbr brbrOur kitchen is equipped to cater to your needs. It features a dishwasher, refrigerator, and stove, ensuring convenience at every turn. We have stocked the kitchen with an array of essential cookware, serving utensils, basic paper products and cleaning supplies for hassle-free dining and upkeep. For coffee enthusiasts, we provide both a drip coffee maker and a Keurig machine, inviting you to bring your favorite coffee blends for a personalized brew. Additionally, the kitchen includes a microwave, rice cooker, toaster and an air fryer enhancing your meal preparation options. A gas grill is also available for guests to use. brbr brbrThe living area is designed for comfort and relaxation. It features an L shaped LoveSac couch, perfect for unwinding or socializing. For entertainment, enjoy our large HDTV with ROKU that allows you to easily log into your apps. brbr brbrAfter a day of beachside fun or exploring the town, head to the lower level where entertainment awaits. Sink into the seating area to watch your favorite shows or movies on the TV or gather around the table for a friendly game of cards or board games. This versatile space is perfect for unwinding, bonding, brbrand creating lasting memories. A half bathroom is also located in this lower area. brbr brbrAnd don't worry about packing too much - a washer and dryer are conveniently located on-site for guest use, allowing you to keep your beachwear fresh and ready for another day of coastal adventures. Basic laundry supplies are available for your use. brbr brbrWe ensure every bathroom is well-stocked for your convenience, providing an array of guest towels along with high-quality shampoo, conditioner, and body wash. Additionally, essential paper products are readily available. For your grooming needs, a hair dryer is provided, ensuring you have everything you need for a comfortable and hassle-free stay.brbrbrbrGuest Access:brbrYou will have access via smart lock to the home

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Exceptional(2)

$501.89

/ Nightly

Private Vacation Home

Beach house with views that has access to Tennis, Basketball and Private Beach.

Old Saybrook, Connecticut, United States

Very quaint and charming New England year-round beach home in a private community with beautiful sunset views. NO PARTIES or GROUPS. This is a very tight-knit community and will only consider people that will treat this home as they would their own. brbrThe home has 3 bedrooms and 2 full bathrooms with an outdoor shower. Both bathrooms have been renovated bathrooms and fresh paint thought out the house. The kitchen floors are new as well. Also, there is a wonderful deck off the rear and outdoor firepit.

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Exceptional(8)

$551.84

/ Nightly

Private Vacation Home

54 Steps to the Beach

Old Saybrook, Connecticut, United States

Beautiful, newly renovated spacious beach house 3 bedroom 2 Full baths. brbr**Bed sheets,blanket, and comforters are NOT provided!!!!br**ONLY TOWELS AND PILLOWS ARE PROVIDED!!!brbrTHOROUGHLY CLEANED AND DISINFECTED. Outdoor porch with dimmable lighting to sit enjoy the beautiful weather. Flat Screen Tvs, in bedrooms and living room, Central Air, Hair dryer, Wifi,Cable, fully stocked kitchen everything you need to cook or eat with, electric stove, fridge, pantry, Washer and dryer, Grill. Walking distance to an amazing private beach down the street with friendly neighbors, sand toys, kid pool available, games such as uno, puzzles,etc. beach chairs,. No pets, No smoking,On site parking, Outdoor shower available. brbrRecommendations for Restaurants nearby: Bills seafood, Log Cabin, Beach donut shop, Pasta Vita(takeout only), Johnny Ads, Waters Edge,The Elks, Cuckoos Nest, The little Pub, Pizzabr

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Exceptional(3)

$1344.06

/ Nightly

Private Vacation Home

Waterfront home in the town of Old Saybrook, CT, walk to beach in a minute.

Old Saybrook, Connecticut, United States

Welcome to our home. The beach is just a minute or 2 away from the home. Truly magically sunrise. If you are on the back of the home you can see sunsets on the patio. It’s a very peaceful place. Our home has three bedrooms and two bath and an office. An amazing home to relax or to share with friends and family.brbr

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Exceptional(1)

$382.13

/ Nightly

Private Vacation Home

Best of Both Worlds

Old Saybrook, Connecticut, United States

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park!brbrThe 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.brWe’ve made great memories there over the years and are now looking to share it with others!brbrThe spacebrThe house is quaint with lots of sunlight- a mix of old and new!brOther things to notebrBeach Access:brIf you plan on driving to the beach you can either pay a daily fee or if you are staying for at least 1 week you can purchase a beach pass to access Harvey’s beach! Renters staying at least 1 week can purchase a 2 week beach pass starting April 15th, 2021. I will send instructions directly to renters once you have confirmed your stay!brbrIf you walk or bike to the beach it is free.

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Rent a place that suits your needs

Private vacation home

View 51 Private vacation home

Most popular vacation rentals in Old Saybrook

Exceptional(1)

$382.13

/ Nightly

Private vacation home

Best of Both Worlds

Old Saybrook, Connecticut, United States

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Bath

Sleeps

Exceptional(1)

$485.10

/ Nightly

Private vacation home

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

Old Saybrook, Connecticut, United States

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Sleeps

Exceptional(1)

$452.00

/ Nightly

Cottage

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

Old Saybrook, Connecticut, United States

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Bath

Sleeps

Exceptional(1)

$445.63

/ Nightly

Private vacation home

Tranquil property, amazing sunsets!

Old Saybrook, Connecticut, United States

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Sleeps

Exceptional(1)

$438.15

/ Nightly

Private vacation home

Perfect Beach House & Academic Rental: 3-Bedroom Home, just steps to Beach!

Old Saybrook, Connecticut, United States

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Sleeps

Exceptional(1)

$425.52

/ Nightly

Private vacation home

Marsh View Home!

Old Saybrook, Connecticut, United States

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Sleeps

Exceptional(1)

$409.30

/ Nightly

Cottage

Charming Old Saybrook Cottage < 1 Mi to Beach

Old Saybrook, Connecticut, United States

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Sleeps

Exceptional(1)

$402.50

/ Nightly

Cottage

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Old Saybrook, Connecticut, United States

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Exceptional(1)

$267.38

/ Nightly

Cottage

Charming 1920's no frills cottage in peaceful Old Saybrook

Old Saybrook, Connecticut, United States

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Exceptional(1)

$296.70

/ Nightly

Cottage

Little Cottage of Gratitude Saybrook Manor walk to beach

Old Saybrook, Connecticut, United States

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Vacation Home Rentals By Owner In Old Saybrook, CT

$845.25

$485.1

$445.63

$425.52

$657.28

$539.91

$614.1

$674.39

$603.75

$467.36

$503.13

$656.2

$609.5

$328.29

$645.27

$501.89

$551.84

$1344.06

$382.13

Rent a place that suits your needs

Most popular vacation rentals in Old Saybrook

$382.13

$485.10

$452.00

$445.63

$438.15

$425.52

$409.30

$402.50

$267.38

$296.70

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