Vacation Home Rentals By Owner In Old Saybrook, CT

***Long Term off season/Academic Rentals with reduced monthly rate*** Kick back and relax in this beach community home in beautiful Cornfield Point. Enjoy a peaceful sunrise or sunset with just a short walk to the beach on Long Island Sound. This 3 bedroom, 1 1/2 bath home is in the perfect location for family vacations and academic rentals. You will have access to the private Cornfield Point beach, tennis courts, basketball court, and playground. The large backyard comes with an outdoor shower and picnic table to enjoy. 2 minute drive to charming downtown Old Saybrook's shops and restaurants, 3 minute drive to Fenwick Golf Course, perfect for beautiful ocean side walks along the causeway. Exterior of property equipped with Nest camera security. You will surely enjoy your stay here!

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

Old Saybrook, Connecticut, United States

Bed

Bath

6

Sleeps

$481.36

Five bedroom family friendly home and the best of Old Saybrook. Our home is close to the beaches, dozens of fine restaurants and The Kate. Our spacious house is newly renovated, with new appliances and bedding. There are two large screen TVs and a foosball table, and an outside deck with barbecue grill.

Old Saybrook family gem very close to local beaches!

Old Saybrook, Connecticut, United States

5

Bed

Bath

8

Sleeps

$1512.88

Welcome to Evertide! Just a short walk to Saybrook Point Resort & Marina, Main Street's restaurants/shops, and the South Cove. Sleeps up to 15 guests, with 5 bedrooms and 3 full baths, making it ideal for family vacations, friends’ getaways, or a multi-family adventure. Enjoy outdoor spaces - covered porches, a gas grill, propane fire pit, and a flat yard for games. Plentiful parking for group travel and pets are welcome. *Host’s other property recently filmed for TV for The Destination Channel.brHighlights:brSleeps up to 15 guests in 5 generous Bedrooms INCLUDES: extra pillows, linens, blankets, room darkening blinds and curtains, white noise machines, and small portable fans. There are a total of 4 king beds, 1 queen sleeper sofa, 5 singles (4 twin beds and and 1 foldable twin cot). All bedrooms have ample closet space for storage. The FIRST floor includes: 1 King Bedroom, 1 Queen Sleeper Sofa in a Den with Roku TV, Mudroom with a washer/dryer, iron, ironing board, and clothes drying rack, Kitchen with a microwave, range (oven + gas stovetop), refrigerator, freezer, coffee & coffeemaker, toaster, all necessary kitchen items, glasses + dishes + utensils + cookware, etc.) The island has 4 stools for additional seating. Dining area comfortably seats ~10. Living area with Roku TV and a decorative (not for guest use) fireplace. The SECOND floor includes: 2 King Bedrooms, Bedroom with 2 Twins, Nook with a foldable Twin cot & Smart TV, 3 Season Sunroom. The THIRD floor includes: 1 King + 2 Singles (a twin bed + twin pull out trundle) within an oversized Bedroom with Roku TV + dedicated workspace. Each of the 3 floors has a full bathroom with a tub + shower, hairdryer, soap , shampoo, conditioner, sink, toilet) Extra personal towels and beach towels provided. Assorted board games and reading material provided. Air conditioning throughout. Free internet/wifi access. The OUTDOOR spaces include: Covered front & side porches, Area for outdoor dining, Gas grill & grilling utensils, Adirondack chairs around a propane fire pit, Backyard cornhole, Ample private parking with room for 6-8 vehicles. Pet friendly for one pet under 50 lbs when declared in advance at the time of booking (additional fee per stay applies). Highchair and pack 'n play (with sheets) available upon request.brbrOld Saybrook is a quintessential Connecticut shoreline town, known for its beaches and coastal vibes. The town's Main Street has unique shops, boutiques, and galleries. Outdoor activities in the local area include swimming, beachcombing, kayaking, and golfing.brbrEvertide is within walking distance or a short car ride to many Old Saybrook favorites - due to its proximity to Saybrook Point, Main Street, and the South Cove: Old Saybrook Resort & Marina including restaurants, entertainment & spa (0.5 miles, 10 minute walk), Mini-Golf at Saybrook Point (0.5 miles, 10 minute walk), General William Hart House (1 miles, 25 minute walk), The Essex Restaurant (1.1 miles, 25 minute walk), Katherine Hepburn Cultural Arts Center - aka The Kate (1.2 miles, 25 minute walk), Paperback Cafe (1.3 miles, 30 minute walk), Mirsina's (1.3 miles, 30 minute walk), Penny Lane Pub (1.4 miles, 30 minute walk), Fenwick Golf Club (1.6 miles, 5 minute drive), Certain Old Saybrook beaches are open to the public, but parking differs between locations. Daily fees may range from $20-30, and non-resident season passes can be $150+ for the season. These include: Harvey’s Beach (public, 3 miles away, 5-7 minute car ride), Town Beach (town residents only, 2.6 miles away, 5-7 minute car ride), Cornfield Point (private, 2.5 miles away, 5-7 minute car ride)brbrIf available, early check-in:br-between 2PM-4PM is at no additional costbr-between 12PM-2PM is subject to a $100 feebr-between 10AM-12PM is subject to a $250 feebrbrIf available, late checkout:br-between 10AM-12PM is at no additional costbr-between 12PM-1PM subject to a $100 feebr-between 1PM-3PM is subject to a $250 feebrbrHost's other short term rental property in Westbrook, CT was recently filmed for The Destination Channel’s Emmy-award winning TV series Staycation, to be included in an upcoming 2026 episode!

Evertide: Walk to Saybrook Point Resort + Main St + South Cove, pet-friendly

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$576.68

brOcean front, sunset facing, property is the only one in the area that has a huge yard and beach. 4-bedrooms, beautiful sunroom, fireplace, gazebo.brbrThe beach in front of the house is sandy with some shells and small rocks (rocky once you get inside the water) and some of it is accessible even at high-tide. The beach is semi-private, accessible only to members of Cornfield Point, which means you might see a few people out there sometimes, especially during peak season (July/August).brbrAir-conditioning is via window units in the bedrooms only. Living areas have quiet oscillating fans. Most find this to be very comfortable because of consistent ocean breeze. brbrThe neighborhood association has tennis and basketball courts as well as a big playground.brbrOld Saybrook is a quiet beach town that's very family friendly. It's also known for it's many great dining options.brbrIn addition to the beach right in front of the house, there are 3 other beaches within a 10-20 min walk. brbrThe first is the Cornfield Point community beach, which is about a 2 min walk from the house. This beach is big and sandy in and out of the water. brbrThe second is the Town Beach, which is 10 min walk from the house. This beach is slightly bigger than the community beach and is also all sandy in and out of the water. This beach also has picnic tables and a store that sells food and beverages.brbrThe third is called Harvey's beach which is another 10 min up the road. This popular beach is uniquely beautiful - sandy, rocky, grassy. Also, has concession stand.brbr4 bedrooms - 2 Queens, 1 Full, 2 Twinsbr2.5 bathsbrBeautiful sunroombrPatiobrGazebobrFireplacebrLiving, Dining rooms brHi-speed WiFi brBBQ, floats, and other beach & lawn games

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$833.75

-- 1910 Shore house; only one surviving the 1938 hurricane on this stretch of beach. Immense lot, gorgeous beach, dunegrass-covered dunes, very private. House is large, with basic amenities. Ideal for the writer and artist.br -- After your swim, towel off and stroll up the sandy path to the porch. Later, enjoy the sunset from the top of one of our dunes. There's no other property like this in Old Saybrook or maybe even all of Connecticut!br --PLEASE NOTE: Generally available for 7 day rentals only (Saturday to Saturday) from mid June to mid September. Shorter stays possible mid May to mid June, and mid Sept thru Oct.. Sometimes available in high season for shorter periods (minimum 3 days), if doesn't overlap with two 7-day rental periods, or at short notice (less than a month, if not otherwise rented). If you are interested in a shorter period, please contact the owner. Not available November through April.br -- Old Saybrook has a convenient Amtrak stop on the Boston-NY line, is just off I-95 between New Haven and New London. The stop is 3 miles and an easy UBER/LYFT ride from the house.br -- Large shaded porch behind our private dunes, with path leading to our private beach. At end of dead-end road. Google Earth: 41o 16' 38.97' N and 72o 24' 26.54' Wbr -- Four bedrooms upstairs (two overlooking the Long Island sound), large living room/dining room area downstairs + kitchen. br -- Unheated, so only available for summer or late spring/early fall rentals.br --Please be advised that this is a century-old vacation cottage with used furniture, sometimes flakey appliances, and perhaps a lump or two in the mattress. It is unheated, and so May & late September can be quite cold; the cottage is not available in the winter months. The shower and bathroom facilities may strike some as primitive. We like it this way -- it's cozy, comfortable, and laid back. But if you strongly prefer, say, the Hilton to camping, this is unlikely to be your cup of tea. Email us for a brochure with more pictures.br -Occupancy is limited to 10 persons. By renting this property, you agree to the rules given below for its use.br -- Please consult VRBO calendar for availability this calendar year.brbrKeywords: HousebrbrThis house is old and delicate, and has been fortunate to have benefited from gentle treatment over the last century by renters and the family that built it. By renting the property and making a deposit through Homeaway/VRBO, the renter agrees to follow the below rules. Thank you for your cooperationbr1) Do not move driveway border stones. They are protecting the underground water supply pipe and septic system.br2) Please respect the Dunes and don’t allow children to play in the area of dune grasses. They can walk on the path in the dunes.br3) No Smoking on premises.br4) Pets are NOT allowed.br5) Tenant must supply their own sheets, personal linens, towels, paper towels.br6) Cottage must be left in clean condition. Please check the following for food spills before you leave: Refrigerator, stove, microwave, toaster over, dining room table & kitchen counter top.br7) You may be billed a cleaning fee if not left in clean condition. Thank you for your understanding.br8) Do not leave any food when you depart.br9) Telephone is available for local calls only. Please use your cell phone or phone calling card for all long distance calls. Tenant will be billed for phone call charges incurred during their stay including a service charge. br10) Please lock all doors and windows when leaving cottage.br11) The right side garage has beach toys etc. for tenant’s enjoyment. Please return items to garage when you are finished with them.br12) The road over the Indiantown Bridge on Nehantic Trail may flood during a storm, especially with a very high tide. Be aware that it is salt water which can damage cars.br13) This cottage is on a septic system. Please flush ONLY white toilet paper and that which leaves the body. PLEASE DO NOT FLUSH DIAPERS OR WIPES.br14) Please put all cooking oils and grease in containers and put in the trash can, NOT down the drain.br15) NO BEACH FIRES, unless you have obtained a required permit from the Old Saybrook Fire Marshall (see Section 2A of https://ecode360.com/8718817). All beach fires are to have such a permit, and are to be below the high tide line and buried when finished. br16) We are not members of Indiantown Association and therefore do not have the right to use their facilities. You are allowed to walk along the entire stretch of beach below the high tide mark. Please use our private beach for swimming, sitting and sunbathing.br17) Our neighbors are close by. Please be considerate of them and do not have late night parties or other noise after 10 pm or before 9 am.br18) Grill must be placed on South side of cottage AWAY from the cottage when being used. Cooking on a grill on either porch or near the building is a fire hazard.br19) Cold Fireplace ash MUST BE put in outside trash bin. Do not leave in fireplace when you depart.br20) No more than 10 people staying overnight or visiting at one timebrbrWe feel that this is a truly special place and we hope you enjoy your stay.

1910 Beach home: CT's most exquisite private beach!

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$757.42

This house is perfect for families or groups that want to enjoy beautiful Old Saybrook in a spacious, newly remodeled, three-story home in a quiet neighborhood close to the beach. This house is perfect for families or groups that want to enjoy beautiful Old Saybrook in a spacious, newly remodeled, three-story home in a quiet neighborhood close to the beach. From the moment the front door opens, the eye is drawn to the marble surround fireplace, transom windows, gleaming hardwood floors and stunning kitchen with soft-close cabinetry, farmhouse sink, high end appliances and quartz topped counters. The kitchen is immaculately appointed with new, top-of-the line appliances and everything you need to cook a gourmet meal. A laundry with a high capacity washer and dryer are available. brOn the second floor, you'll find 3 bedrooms (Queen,Queen, Full+Twin trundle) with hardwood floors and ceiling fans. Ascend to the third floor for the Master Suite with abundant closet space, vaulted ceiling, balcony with views of LI Sound and a spa master bath with double sinks, walk-in shower, and an over sized soaking tub. brIn addition to all this, there is high speed internet WiFi access and a large finished recreation room in the basement with a full bath. Watch all your favorite shows on Chromecast TV on a large HDTV. brAfter a day outside, you can clean-up in your private outdoor shower when you return from to the highly desirable private Cornfield Point Beaches, just a stroll away. Then sit on the mahogany deck in afternoon shade and fire-up dinner on the Weber gas grill. brPlease note that all linens and towels are provided and will be fresh when you arrive.

Spacious And Luxurious Beach Home Steps From The Water

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$525.48

brExplore 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. Convenient to great dining and shopping, this home offers a mix of relaxation and excitement. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook!brbrPlease note Our property is strictly an animal-free zone due to severe allergies persisting in the family.brbrThe Neighborhood:brWelcome to the charming Great Hammock Rd neighborhood in Old Saybrook, CT! Nestled near the beach, this coastal community offers scenic beauty, a tight-knit atmosphere, and convenient access to amenities. Enjoy a blend of tranquility and recreation, with historic richness adding to the neighborhood's allure. Experience coastal living at its best in this welcoming community.brbrGetting Around:brWalking: The charm of this coastal community is best experienced on foot. Take a leisurely stroll to the nearby beach or explore the tree-lined streets for a delightful walk. To walk to the beaches take a right from the driveway, all the beaches are located on the right side of the road.brbr Biking: Enjoy the scenic routes with provided bikes. Pedal your way through the neighborhood and soak in the coastal beauty.brbr Local Transport: For longer journeys or nearby attractions, consider rideshare services or local transportation options. Convenient and accessible for your explorations.brbrbrbrParking in the Great Hammock Rd neighborhood is hassle-free:brbr Designated Parking: Each property has designated parking areas. Please park only in the assigned spots to ensure a smooth flow of traffic.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$1245.83

Our NEWLY RENOVATED cozy cottage is right on the beach. You can’t get any closer than a home on the beach. Great fishing spot out the back door, paddleboarding, swimming, kayaking, sunsets, long walks, great local bike trail. brbrLocated only minutes from downtown Old Saybrook. brbrThere are two bathrooms, one is located on the first floor (1/2 bath) near the entrance and kitchen. The second full private bathroom is located on the second floor. Also included in your stay is an outdoor shower with hot and cold water.brbrWhat to Do brTwo major shopping premium outlets, Westbrook and Clinton. Award winning casinos, Foxwoods and Mohegan Sun. Close to Mystic Seaport, Mystic Aquarium, Gillette Castle, the New London ferry which departs daily to Block Island and Long Island. Beautiful beaches. New Haven nightlife 25 minutes south on I-95 or Middletown’s restaurant’s 25 minutes north on Rt. 9. brbrGetting Around brTrain station is 3 miles from the cottage for easy travel to Boston and New York located in Old Saybrook with complimentary parking. Essex Taxi and Uber provide transportation services in town. brbrOther Things to Note. The Town in-forces sound ordinance at 10PM every night.brbrAcademic rental available. br

Cornfield Point Cottage

Old Saybrook, Connecticut, United States

4

Bed

Bath

9

Sleeps

$928.63

A perfect retreat to relax and enjoy this private beach, the amazing sunsets and our special town! Located in family-friendly Cornfield Point Association (CPA) in Old Saybrook, CT, this beautiful coastal luxury home offers 4 bedrooms - 2 king and 2 queen beds. Sleeps 8+ comfortably, with room for air mattresses to expand sleeping space. Home offers a quiet space to work, a full service oversized eat-in kitchen with a dining area and bar, a large living room, den and great outdoor patio and large fenced in yard. One king ensuite is located on the first floor with a large smart TV. The other king bedroom is on the 2nd floor and offers a smart TV with a sitting room attached. The 2 queen bedrooms are located on the 2nd floor. There are 2 full baths (one bathtub/shower, one shower) and 1 powder room. Home offers WiFi, Central Air Conditioning, forced hot air central heating, washer/dryer, and waterviews, along with all the amenities of home. The lovely private outdoor patio has an eating space, grill and lounges. It's a quick walk to the CPA’s private sandy beach, rocky beaches, clubhouse, tennis, pickleball, basketball or other activities in the Association. It's a close drive to The Kate theatre, Saybrook Point spa, the Fenwick 9 hole public golf course, mini golf, many great restaurants and loads of events and things to do! Easy check-in options, with on-site parking. Great flat area for biking and walking, no busy roads. Home is smoke free. Sorry, no pets allowed.

Luxury coastal home in located in Cornfield Point, sleeps 8+.

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$1002.25

Escape to this ultimate beachfront retreat at our beautifully updated home, where cooling sea breezes and the warmth of modern amenities await. With comfortable sleeping arrangements for up to 12 guests, you’ll create lasting memories against the backdrop of the Long Island Sound.brbrBeachfront Bliss:brStep onto the deck and immerse yourself in the tranquility of your private beach area. Marvel at the stunning views as you soak up the sun, and for even more space to unwind, access the expansive Chalker association beach just to your right.brbrOpen Concept Living:brInside, our 1100 sqft open-concept layout seamlessly combines the kitchen, living room, and dining area. The result An uninterrupted view of the vast Long Island Sound. The dining area comfortably seats 10, and for outdoor dining, there’s room for 12. The kitchen is fully equipped with new stainless steel appliances, including an ice maker fridge and stove. You’ll also find a grill for outdoor culinary adventures, and for coffee lovers, a Keurig with a traditional coffee pot.brbrBedroom Bliss:brThe master bedroom boasts a plush hybrid king bed, a large TV, and a private entry door to the beach. The modernized walk-in shower adds a touch of luxury. The second bedroom features a queen-size bed and a TV, with sliding doors that reveal breathtaking water views. Up in the loft, there’s individual sleeping space for 6, all with twin-size beds and trundles. For those who relish waking up to the sunrise, a daybed with a trundle accommodates 2 more guests. Two full bathrooms, one with a new walk-in shower, provide convenience.brbrAll the Comforts:brWe provide linens, including bath and beach towels, making your stay hassle-free. A brand-new washer and dryer are available for any laundering needs. For aquatic adventures, we offer an inflatable paddleboard, kayak, water mat, and water trampoline. Please use these items at your own risk, releasing liability.brbrEntertainment & Connectivity:brStay connected with high-speed Wi-Fi (400+ mbps). You can also enjoy your favorite streaming services like YouTube, Netflix, Hulu, and more if you sign in on your own accounts. A cleaning fee of $200 applies, and with prior approval, trained pets are welcome for $25 per night during your reservation. To ensure a pleasant stay for all guests, kindly refrain from allowing pets on furniture or beds.brbrNearby Attractions:brDiscover the area’s attractions, including the Clinton Premium Outlets just 10 minutes away. Within a 30-minute drive, you can explore the Mystic Aquarium, Mohegan Sun Casino, Foxwoods Casino, and prestigious Yale and New Haven University.brbrWe’re thrilled to offer this serene space for you to create memories that will last a lifetime. For more options, check out our other listing on Vrbo: #7555663 The Count House in Clinton, Connecticut,” just four houses away from two beaches and an 8-minute walk to Clinton town beach and playground. It features 4 bedrooms, 2 bathrooms, and sleeps up to 13 people.

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$560.0

Welcome to Old Saybrook and Cornfield Point! It's time to relax. Our recently updated beach house has all the special touches that make it the perfect retreat for couples or families. Enjoy the private beach access just a short walk away, the spectacular Old Saybrook sunsets, and the friendly town ambiance. Our home “Shore Beats Work.”brbrThe Spacebr“Shore Beats Work” was completely updated in 2022. Our home has 3 bedrooms, 2 full baths, an outdoor shower, and a lovely patio. The new split AC units and ceiling fans will keep you cool after those hot days on the beach. It is fully furnished with linens, towels, shampoo and conditioner, making your packing easy and light! Our newly seeded backyard with privacy fence welcomes you to relax, unwind and grill. Bikes are provided to ride to the beach or to main street. Our home is cozy but has everything you need.brbrThe AreabrbrCornfield PointbrCornfield Pont is a shoreline community in Old Saybrook. You are within walking distance (.3 miles) to the private association beach. The beach amenities include a boat ramp for non motorized vessels, showers, benches, and palm trees.brbrOld Saybrook and Beyond brNeed a break from the beach Head to Main St for local shopping, coffee, ice cream and fine dining. See a show at The Kate theater.brbrOld Saybrook is conveniently located near numerous attractions. Travel just a little further to Mystic and visit the Aquarium or Seaport. In Essex, you can ride the historic steam train or relax aboard the riverboat on the CT River. Want to try your luck at the casino Head to Mohegan Sun or Foxwoods. Would rather go shopping The Westbrook and Clinton Outlets are just a short drive away. Escape for the day to Newport, RI or board the New London ferry to Block Island. Our convenient location offers endless adventures for everyone rain or shine. brbrAdditional Amenities:brBikes (2)brWagonsbrBeach Chairs (8+)brBeach Umbrella Beach ToysbrDriveway parking (3 spots) Exterior protected by Blink security camera

Cornfield Point Beach. Family Friendly. Beach Getaway. SHORE BEATS WORK!

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$286.35

Updated furnishings, and freshly painted. Full bath with easy to clean flooring and full size washer and dryer. Inviting and cozy, pet friendly beach house in a small private association. Large open living space with fully stocked kitchen, dining room and desk area to work remotely if you need to. Generously sized, fully fenced yard for your fur babies, with a patio and picnic table. Well appointed, with all the comforts of home, and bright open space. Walk 2/10 mile to a private beach. Streaming enabled TV and wifi included. You'll never want to leave!brbrThe PropertybrbrEscape the noise of the city and hide away at this lovely cottage!brbrCOMMUNITY AMENITIES: Easy access to private Saybrook Manor Association beach so swimming, boating, and all kinds of CT shoreline activities are at your fingertips!brbrOUTDOOR LIVING: Patio table and chairs for 6. Folding wagon to take to beach, beach towels.brbrINDOOR LIVING: Smart TV, dining table with seating for 6, breakfast bar with seating for 2 more, full size bathtub, plenty of closet space, iron and full size ironing board. Playing cards, Uno and puzzles.brbrKITCHEN: Fully equipped, microwave, Keurig, drip coffee maker (including complementary coffee and tea), cooking basics, baking sheets/dishes, complimentary spices, dishware/flatware, lobster pot and accessories (shell crackers and shrimp forks).brbrGENERAL: Free WiFi, washer/dryer, bedding linens and towels included, central heating, keyless entry, complimentary toiletries, cleaning essentialsbrbrPARKING: Driveway (4 vehicles)brbrHouse Rules and Policiesbr- No smokingbrbr- Pet friendly - NO MORE THAN TWO PETS allowed at one time. brbr- No events, parties, or large gatheringsbrbrPets welcome with a small fee paid up front.brbrClose to all kinds of activities and shoreline fun.brbrHarvey's Beach 2 milesbrMonkey Farm 1.7 milesbrStarbucks 1.8 milesbrOld Saybrook Town Launch 2.7 milesbrSaybrook Point Marina 3 milesbrMystic Seaport 28 milesbrMystic Aquarium 28 MilesbrClinton Premium Outlets 8 milesbrbr*WE STRONGLY ENCOURAGE YOU TO GET TRIP INSURANCE*brWe have exterior cameras, one at the front and one at the back of the property to protect it during vacancies and weather events.

Steps to the Beach, Cozy Year Round Cottage Pet Friendly

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$506.77

You will fall in love with this beautiful beach house in the sought-after Indian Town beach. Beautiful views of Harvey Beach, a comfortable outdoor area to relax and spend time with your family, two private beaches with a harbor that has panoramic views of Long Island Sound less than a 2-minute walk away! brbrEnjoy the small-town feel of a great community where you can walk bike, swim. Spectacular low tides await you!brbrRestaurants, outlets, and attractions all nearby. Perfect location to explore the Ct Shoreline.brbrThis home is our happy place, and we look forward to sharing it with you!brbrImportant - House is Fema Certified, so the living area is on the upper level. There is not ground-level living space, and there is an exterior staircase. brbrSmall well-trained pet welcome! An additional deposit/cleaning fee,brbrImportant Note: Garage is storage, not for parking guest automobiles. brGolf cart is not available for use.

Beach House steps to private beaches in sought after location!

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$996.67

Newly renovated beach home available for the first time! Beautifully updated home in the Chalker Beach community of Old Saybrook! Best of both worlds, path to the beach right in front of the house perfect for a morning or evening walk and the marsh in the back. Short 2 minute walk to the sandy association beach for swimming. 3 minute walk to playground and bball court located on Tucker Rd. Double lot and wide driveway for parking. Enjoy the sound of the waves with views of the ocean and the marsh in back. 600 sqft deck with 3 seating areas and new gas grill. brbrSpacious living room with sleeper sofa and sunroom with wall of windows looking out to the water. Fully stocked leathered granite kitchen with subway tile backsplash and brand new appliances. 1 bedroom looks out over the marsh and 2 front bedrooms have ocean views. Perfect beach home all updated and very comfortable. We provide everything you will needed: toiletries, linens, beach and bath towels, coffee, tea, beach chairs, sand toys, beach blanket. paddle board, kayak and red wagon to transport everything down to the beach. Don’t forget to tag @chalkerbeachcottage during your stay. Enjoy a day at the beach and then come home and use the outdoor shower!

Chalker Beach House Steps to the Water!

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$345.0

Welcome to your South Cove waterfront getaway in Old Saybrook! This one-bedroom waterfront retreat is the perfect spot to relax and recharge. Wake up to spectacular sunrises, then spend the day exploring town—restaurants, shops, galleries and The Kate are all just minutes away, with beaches close at hand.brbrBack home, fire up the grill and enjoy dinner on the deck with front-row views of the cove. Watch ospreys circle their nest, egrets wade along the shore, and swans drift by as the evening winds down. Comfortable, convenient, and surrounded by natural beauty, this charming retreat puts the best of the Connecticut shoreline right at your doorstep.

Charming Waterfront Getaway — South Cove, Old Saybrook

Old Saybrook, Connecticut, United States

Bed

Bath

2

Sleeps

$726.8

Gather your people at our 1795 historic homestead near Coastal Connecticut, ideal for reunions, retreats & wedding weekends. Cook & linger in the well-stocked kitchen, read fireside or spread out across the private lawn and porches. A character-rich, memory-making home!brbr⭐ “Full of character, spacious and comfortable—our family loves coming back.” – Stephenbrbr🏜 HIGHLIGHTSbr✓ Authentic 1795 historic estatebr✓ Private grounds, porches, firepitbr✓ Well-stocked kitchen & cozy fireside spacesbrbrTHE SPACEbrbr***Message us for weddings or other large events!***brbrHistoric charm with private grounds, fireside rooms, porches, and a cook-ready kitchen.brbr🏷 Main FloorbrbrKitchen & Dining Room br∙ FULLY stocked kitchen w/plenty of counterspace for at-home baking and cookingbr coffee maker, tea kettle, blender and toasterbr∙ Cooking oils and seasoning essentials br∙ Abundance of dishware, glassware and silverware, including children’sbr∙ Full-sized fridge and freezerbr∙ Gas stove and ovenbr∙ Microwavebr∙ Dishwasherbr∙ Blenderbr∙ Slow cookerbr∙ Dining room table, seating for 4brbrLiving Room br∙ Smart TVbr∙ Netflix, Prime Video, Disney Plus, Hulu, HBO and morebr∙ Sound systembr∙ Fireplacebr∙ Board gamesbr∙ Booksbr∙ ToysbrbrBedroom #1 (Primary Bedroom)br∙ King size bedbr∙ Premium mattress and comforterbr∙ Bedside table and lampbr∙ Large closet w/ hangersbr∙ Booksbr∙ MirrorbrbrBedroom #2br∙ Queen size bedbr∙ Premium mattress and comforterbr∙ Room darkening shadesbr∙ Bedside table and lampbr∙ Large closet w/ hangersbrbrBedroom #3br∙ 2 Double bedsbr∙ Premium mattress and comforterbr∙ Room darkening shadesbr∙ Bedside table and lampbr∙ Large closet w/ hangersbr∙ BooksbrbrBathroom #1 and Laundry Roombr∙ GE high-efficiency washer/dryerbr∙ Tide Free and Gentlebr∙ Showerbr∙ Single vanity and mirrorbr∙ Shampoo, conditioner and body soapbr∙ Makeup washclothbrbrBathroom #2br∙ Showerbr∙ Bathtubbr∙ Single vanity and mirrorbr∙ Shampoo, conditioner and body soapbr∙ Makeup washclothbrbr🏷 2nd FloorbrbrBedroom #4br∙ Double bedbr∙ Single bedbr∙ Premium mattress and comforterbr∙ Room darkening shadesbr∙ Bedside table and lampbr∙ Large closet w/ hangersbrbrBedroom #5br∙ Queen size bedbr∙ 2 Single bedsbr∙ Premium mattress and comforterbr∙ Room darkening shadesbr∙ Bedside table and lampbr∙ Large closet w/ hangersbr∙ Ceiling fanbr∙ Full-length mirrorbrbrHallwaybr∙ Office table and chairbrbr🏷 Outdoor Space(s)brbrSunroom br∙ Large glass roof for natural sunlightbr∙ Comfortable sofabr∙ Rocking chairbrbrBackyardbr∙ Firepitbr∙ Outdoor seatingbr∙ Play areabr∙ Picnic tables and umbrellabrbrBalconybr∙ Outdoor seatingbr∙ Coffee tablebrbrPorchbr∙ Enclosed porch br∙ Outdoor seatingbrbr🏷 Parkingbrbr∙ Room for 6 vehicles but can hold up to 50+ for large events (contact us for details)brbr🚘 NearbybrbrMain Street Shops & Boutiques (walking ~3 min): Charming local shopping, antiques, galleries and cafés in the heart of Old Saybrook.brAshlawn Farm Coffee (drive ~2 min): Local favorite café with specialty coffee, pastries, sandwiches and outdoor seating.brMonkey Farm (drive ~3 min): Popular bar & grill with classic fare and laid-back vibe.brPaperback Cafe (drive ~3 min): Cozy breakfast/brunch spot with community favorites.brSwell (drive ~3 min): Highly rated acai & healthy café option on Main Street.brJames Pharmacy Bed & Breakfast and Gelateria (drive ~4 min): Historic gelato and coffee stop with old-town charm.brFresh Salt (drive ~5 min): Upscale seafood dining with seasonal and local offerings.brCafe Toscana (drive ~4 min): Casual coffee & tea spot for daytime breaks.brOtter Cove Restaurant & Bar (drive ~7 min): Stylish gastropub with seasonal local menus.brSaybrook South Green & Historic Sites (drive ~5 min): Historic district featuring the Humphrey Pratt Tavern and heritage architecture.brThe Kate – Katharine Hepburn Cultural Arts Center (drive ~4 min): Live theater, arts and tribute exhibits to the legendary actress.brSaybrook Breakwater Light (drive ~6 min): Iconic sparkplug lighthouse and peaceful waterfront setting.brLynde Point Light (drive ~6 min): Historic Long Island Sound lighthouse ideal for photography and scenic views.brOld Saybrook Town Beach (drive ~7 min): Saltwater beach with seasonal swimming and sunbathing.brHarvey’s Beach (drive ~9 min): Popular sandy shore and summer gathering spot on Long Island Sound.brCrystal Lake Town Park (drive ~5 min): Community park with playgrounds, trails and open recreational space.brbrTanger Outlets Westbrook (drive ~7 min): Outlet shopping with over 150 brands for fashion and gifts.brRocky Neck State Park (drive ~15 min): Beach, camping, hiking and nature trails.brHammonasset Beach State Park (drive ~26 min): Connecticut’s largest shoreline park with miles of sandy beach and boardwalk.brEssex Village (drive ~20 min): Historic small town with antique shops, riverfront views and dining (great half-day trip).brbr💡 Other things to notebr✓ This is a true historic home, full of charm and character, which means you may notice older-home quirks that come with a property from the late 1700s.br✓ The home sits near a main road, so you may hear some traffic at times, though the yard and grounds feel private once you’re settled in.br✓ The beach is ~5 minute drive from the property.br✓ Some areas on the property are reserved for caretaking and maintenance use and aren’t accessible to guests.

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Old Saybrook, Connecticut, United States

Bed

Bath

Sleeps

$425.5

This water view, beach access home is located just one house away from the beach. The house features four bedrooms, one full bath and one outdoor shower. Bountiful fine white sand beaches are just a few steps down your own private path to the beach. brThis beach access home is located on Toms Road in a very private section of Plum Bank Beach within Old Saybrook. Plum Bank is a strip of fine white sand bordered on one side by Long Island Sound and on the other side by acres of salt marshes.brbrSafe swimming conditions for children because of small waves, no undertow, and no fast drop off. Low tide reveals hundreds of yards of clean sandbars and shallow tidal pools which are a great place for kids to play safely and for long walks.brStriped Bass are readily caught by surf casting from the beach in front of these homes.brWalk on your private path to the beach about 75' away.brbrThis house is adjacent to a vacant lot owned by the same owner. The vacant lot abuts the salt marsh tidal waterway. The vacant lot has a private boat launch ramp that may be used at your own risk to launch a lightweight shallow draft boat. The vacant lot may also be used for additional parking.

Saybrook Almost Beach-Front, Private Beach, Boat Launch, Shallow Dock, Secluded

Old Saybrook, Connecticut, United States

4

Bed

Bath

8

Sleeps

$805.0

Experience Old Saybrook like a local in this wonderful 3-bedroom house. The space features two queen beds and a cozy 2 twin beds, perfect for families or groups. With two bathrooms, guests enjoy plenty of privacy and convenience. The house stays comfortable with air conditioning, and thoughtful touches like an iron and hair dryer make packing light easy. Step inside to find an inviting atmosphere where you can relax after a day of exploring. This enchanting home offers a nice blend of comfort and charm for your stay. We look forward to hosting you at our place.

Chalker Beach, Beachfront Home in Old Saybrook, Connecticut,

Old Saybrook, Connecticut, United States

Bed

2

Bath

6

Sleeps

$390.05

Walk to beach! Comfy older house in CT most special shoreline. Private beach & tennis and basketball courts with short drive to legendary Fenwick Golf Course. Easy access to trains and charming village. Come take a look or send a friend........more photos available. brMessage us !

Cozy Beach House - 5 min walk! to Knollwood Beach

Old Saybrook, Connecticut, United States