Home Vacation Rentals By Owner In Old Saybrook, CT

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$928.63

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Private Vacation Home

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

Old Saybrook, Connecticut, United States

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.
Bed 4

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Bath 2

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Exceptional(37)

$1002.25

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Private Vacation Home

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

Old Saybrook, Connecticut, United States

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.
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Bath 2

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Sleep 12

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Exceptional(16)

$560.0

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Private Vacation Home

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

Old Saybrook, Connecticut, United States

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
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Exceptional(52)

$286.35

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Private Vacation Home

Steps to the Beach, Cozy Year Round Cottage Pet Friendly

Old Saybrook, Connecticut, United States

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.
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$726.8

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Private Vacation Home

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

Old Saybrook, Connecticut, United States

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.
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Exceptional(6)

$210.41

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Cottage

'Grandma's Cottage' w/ Sunroom: Walk to Beach

Old Saybrook, Connecticut, United States

Take a step back in time and embrace a peaceful retreat from the comfort of this 3-bedroom, 1-bathroom vintage vacation rental. With a kitchen, a cozy living area, and 2 sunrooms, this property will make you feel right at home. Head out for fun in the sun and sand at the beach, visit Main Street in Old Saybrook to visit unique shops, or tour the Katharine Hepburn Cultural Arts Center. Whether you're staying with a few friends or planning a family trip, adventure is right around the corner!brbr-- THE PROPERTY --brbrBuilt in 1938 | Free WiFi brbrBedroom 1: Full Bed | Bedroom 2: Twin Bed | Bedroom 3: 2 Twin Beds brbrINDOOR LIVING: TVs, dining table, high chair, books, board games brOUTDOOR LIVING: Outdoor seating areasbrKITCHEN: Stove, fridge, coffee maker, microwave, toaster oven, dishware/flatware, basic cooking essentialsbrGENERAL: Free WiFi, window A/C unit (only in living room), towels/linens, beach towels, hair dryer, complimentary toiletries, trash bags/paper towels brSUITABILITY: 2 steps required to access, pet fee (paid pre-trip)brPARKING: Grass parking area (3 vehicles)brbr-- THE LOCATION --brbrBEACHES: Saybrook Manor Beach (walking distance), Harvey's Beach (1.8 miles)brATTRACTIONS: Katharine Hepburn Cultural Arts Center (1.7 miles), Fort Saybrook Monument Park (3.0 miles), White Squirrel Woods (3.6 miles), Saybrook Breakwater Lighthouse (4.8 miles), Ferry Landing State Park (5.6 miles)brSHOP AROUND: Main Street (1.6 miles), Re-Unique Antiques (1.1 miles), Pearls and Plaid (1.8 miles), Old Essex Saybrook Antiques Village (4.3 miles)brAIRPORTS: Tweed New Haven Airport (27.9 miles), Bradley International Airport (58.3 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: 1 bathroom consists of a toilet and a sink, the shower for the bathroom is located in a different roombr- NOTE: The cottage has electric heat however it is not insulated and can be chilly during the cooler months
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