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Old Saybrook, CT vacation rentals
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Best Vacation rentals and Airbnb offers in Old Saybrook, CT

Best Old Saybrook, CT vacation rentals with a balcony

Seaside Sanctuary Steps From Long Island Sound - Old Saybrook, CT
10 2 reviews

Seaside Sanctuary Steps From Long Island Sound

apartment, Westbrook
This Westbrook, Connecticut vacation home, located in Westbrook Center a block from Route 1 and five minutes from Route 95, offers easy access to local restaurants, the marina, and downtown Westbrook, placing you near the Katharine Hepburn Cultural Arts Center.
This 2,800-square-foot house features four bedrooms, two bathrooms, sleeps ten guests comfortably, includes a fully equipped kitchen, open living/dining area, outdoor shower, ample parking, and direct beach access for swimming and proximity to motor boating.
Beautiful 3-bedroom House With Ac In Charming Old Saybrook. Bird Bliss. - Old Saybrook, CT
No reviews

Beautiful 3-bedroom House With Ac In Charming Old Saybrook. Bird Bliss.

apartment, Old Saybrook
This 3-bedroom, 3-bathroom condo is located in the Saybrook Manor district of Old Saybrook, a 5-minute walk to Chalker Beach and a 6-minute drive to the Katharine Hepburn Cultural Arts Center.
This pet-friendly rental accommodates up to 6 guests and offers air conditioning, Wi-Fi, and is conveniently situated near local marinas and historical sites like the General William Hart House.
Beachfront Home With Amazing Views | 5br Sleeps 11 - Old Saybrook, CT
No reviews

Beachfront Home With Amazing Views | 5br Sleeps 11

apartment, Old Saybrook
This 5-bedroom beachfront house in Old Saybrook offers direct waterfront access within the private Saybrook Manor community, just a short drive from Saybrook Country Barn and Tanger Outlets.
This family-friendly vacation rental accommodates up to 11 guests with a fully equipped kitchen, an outdoor patio with a griddle, and in-unit laundry, perfect for a comfortable stay with amenities like high-speed Wi-Fi and air conditioning.
Walk To Beach, Pool, Tennis Court And Kids Playscape. - Old Saybrook, CT
No reviews

Walk To Beach, Pool, Tennis Court And Kids Playscape.

apartment, Westbrook
This Westbrook Center vacation home is conveniently located less than half a mile from Westbrook Town Beach, within three miles of Tanger Outlets and Clinton Plaza Shopping Center, and six miles from historical sites like the Adam Stanton House and General Store Museum.
This two-bedroom, three-bathroom house sleeps six guests and boasts a fully equipped kitchen, in-unit laundry, a private swimming pool, tennis court, and a terrace – perfect for enjoying the outdoor barbecue grills and garden.

Browse Family-Friendly Vacation Rentals in Old Saybrook, CT

These family-friendly vacation rentals in Old Saybrook, CT offer spacious layouts and easy access to local beaches.

Hot Tub & Firepitsunsets & Beach Walk | Fireplace - Old Saybrook, CT
10 102 reviews

Hot Tub & Firepitsunsets & Beach Walk | Fireplace

apartment, Old Saybrook
This Old Saybrook retreat, located on Great Hammock Road, offers easy access to Old Saybrook's attractions and proximity to the beach.
The three-bedroom house sleeps eight guests comfortably, boasting a fully equipped kitchen, Jacuzzi, fire pit, indoor fireplace, and bikes for exploring, plus a living room with a pull-out queen bed and a family room with a full-size futon.
Cheerful, Private Cottage In Essex Village. - Old Saybrook, CT
9.9 67 reviews

Cheerful, Private Cottage In Essex Village.

apartment, Essex
This charming cottage is located in Essex Village, just a short walk from downtown Essex, offering easy access to shops, restaurants, and the waterfront. The cottage consistently receives excellent ratings for location, cleanliness, and overall experience.
The cozy cabin features one bathroom and comfortably sleeps three guests. It comes fully equipped with a kitchen, air conditioning, a private garden, and parking, making it perfect for a relaxing getaway.
Fully Updated Cornfield Point Beach House, Old Saybrook, Ct - Old Saybrook, CT
10 6 reviews

Fully Updated Cornfield Point Beach House, Old Saybrook, Ct

apartment, Old Saybrook
This renovated cottage is located in Old Saybrook, a short distance from Cornfield Point Association and its rocky beach. It has received excellent ratings from previous guests.
The house offers a comfortable and modern stay with 3 bedrooms and 1 bathroom, accommodating up to 7 guests. You'll enjoy access to a private beach, a boat ramp, a tennis court, a basketball court, and parking for a trailer.
Great Hammcock Getaway, Cozy Home, Hot Tub, Fire Pit, Beaches Nearby. - Old Saybrook, CT
10 11 reviews

Great Hammcock Getaway, Cozy Home, Hot Tub, Fire Pit, Beaches Nearby.

apartment, Old Saybrook
This Old Saybrook seaside home, located within two miles of Harvey's Beach and the Katharine Hepburn Cultural Arts Center, offers stunning ocean views and easy access to local attractions.
This 1,160-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, Jacuzzi, tennis court, and free WiFi.

Frequently Asked Questions about vacation rentals in Old Saybrook, CT

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Best Old Saybrook, CT vacation rentals with parking

Sunsetskies 2ndfl | Filmed 4 Tv+walk 2 Watersedge - Old Saybrook, CT
10 8 reviews

Sunsetskies 2ndfl | Filmed 4 Tv+walk 2 Watersedge

apartment, Westbrook
This fully renovated second-floor apartment is located in Westbrook, Connecticut, just a short walk from the popular Water's Edge Resort & Spa and within easy reach of Westbrook's main attractions and beaches. The apartment is perfect for families or groups, with three bedrooms and a capacity of six guests.
The apartment features a fully equipped kitchen, a washer and dryer, free high-speed internet, a spacious living area with a Roku TV, a private backyard with a gas grill, and two dedicated parking spots. Enjoy stunning sunset views from the spacious outdoor deck, perfect for relaxing and dining al fresco.
Addisons Oasis - Old Saybrook, CT
9.7 6 reviews

Addisons Oasis

apartment, Old Saybrook
This Old Saybrook beachfront cottage offers direct access to a private beach and stunning Long Island Sound views.
The three-bedroom, one-bathroom rental sleeps seven guests and includes a fully equipped kitchen with a refrigerator, microwave, and dishwasher, plus air conditioning, internet, parking, and a garden.
Saybrook Point Resort And Marina. - Old Saybrook, CT
No reviews

Saybrook Point Resort And Marina.

resort, Old Saybrook
The Saybrook Point Resort And Marina is located in Old Saybrook Village, a short stroll from the town center, Old Saybrook shoreline, Old Saybrook Main Street shops and dining, and the Katharine Hepburn Cultural Arts Center.
This resort offers parking and is a short drive to the Connecticut River, providing a tranquil retreat ideal for exploring the coastal beauty of the region.
Coastal 3br W/ Double Living Areas | Beach Access - Old Saybrook, CT
9.5 4 reviews

Coastal 3br W/ Double Living Areas | Beach Access

apartment, Old Saybrook
This Old Saybrook beach house, a short walk from the private Fenwood Beach, offers easy access to Old Saybrook's coastal attractions.
The three-bedroom, two-bathroom home sleeps six and features two living areas, a fully equipped kitchen with modern appliances including an air fryer and Keurig, on-site laundry, and a gas grill; guests enjoy access to a large HDTV with Roku, board games, and ample towels and toiletries.

Choose the Right Vacation Rentals with a Pool in Old Saybrook, CT

A vacation rental with a pool in Old Saybrook, CT is the ideal way to complement your daily coastal adventures.

Luxe 5,600-sq-ft Estate Waterfront + Pool - Old Saybrook, CT
No reviews

Luxe 5,600-sq-ft Estate Waterfront + Pool

apartment, Westbrook
This Westbrook vacation home offers unobstructed ocean views and direct access to Westbrook Harbor, conveniently located on the Connecticut Shore.
This expansive 5-bedroom, 5-bathroom estate accommodates up to 12 guests and features a heated outdoor pool, chef-grade kitchen with a Miele coffee maker, indoor entertainment with a pool table and wet bar, and step-free entry with a first-floor bedroom and bathroom for accessibility.
3br Updated Cottage W/ Pool In Old Saybrook - Old Saybrook, CT
9.9 77 reviews

3br Updated Cottage W/ Pool In Old Saybrook

apartment, Westbrook
This charming cottage is located in Old Saybrook, Connecticut, just minutes from beautiful beaches and a short drive from popular towns like Mystic and Essex. It boasts excellent ratings for user experience, location, and cleanliness.
The three-bedroom cottage comfortably sleeps six guests and features a private pool, a spacious yard, and a modern kitchen with a fridge, freezer, and microwave. You'll also enjoy access to air conditioning, parking, and a garden.
Luxe 5,600-sq-ft Estate Waterfront + Pool - Old Saybrook, CT
10 1 review

Luxe 5,600-sq-ft Estate Waterfront + Pool

apartment, Westbrook
This seaside rental in Westbrook Center offers unobstructed ocean views and direct access to Westbrook Harbor, with West Beach 3 miles away and popular dining spots like Bill's Seafood Restaurant 3 miles and Lenny & Joe's 4 miles away.
This 5600 sq ft residence accommodates 12 guests with 6 bedrooms and 6 bathrooms, featuring two chef-grade kitchens, a kitchenette, a heated outdoor pool, a fire pit, a pool table, a wet bar, and step-free entry with a first-floor bedroom and bathroom.
Saybrook Point Pool House - Old Saybrook, CT
No reviews

Saybrook Point Pool House

apartment, Old Saybrook
This historic, renovated barn offering 3 bedrooms and 2 bathrooms for up to 6 guests is located in Old Saybrook's North Cove neighborhood, just one block from the Saybrook Point Inn and the Connecticut River.
This maritime-themed rental features air conditioning, a kitchen, internet, parking, a swimming pool, and a patio, situated on Captain Tooker's 1890 estate.

Browse Waterfront Vacation Rentals in Old Saybrook, CT

Discover relaxing coastal properties with these seaside vacation rentals in Old Saybrook, CT, located near the shore for an ideal beach-town escape.

Old Saybrook Waterfront Luxury Cornfld Pt 3bdrm - Old Saybrook, CT
10 5 reviews

Old Saybrook Waterfront Luxury Cornfld Pt 3bdrm

apartment, Old Saybrook
The Happy Place - Old Saybrook, CT
10 56 reviews

The Happy Place

apartment, Old Saybrook
Escape To Our Waterfront House In Old Saybrook Ct - Old Saybrook, CT
9.9 47 reviews

Escape To Our Waterfront House In Old Saybrook Ct

apartment, Old Saybrook
White Bird Beachfront. Dock Available Extra. - Old Saybrook, CT
9.7 38 reviews

White Bird Beachfront. Dock Available Extra.

apartment, Old Saybrook

Traveler-Approved Luxury Vacation Rentals in Old Saybrook, CT

Experience 5-star comfort in a luxury Old Saybrook, CT vacation rental designed with premium amenities throughout.

Sunrise Beach Cottage - Old Saybrook, CT
10 37 reviews

Sunrise Beach Cottage

apartment, Old Saybrook

Explore Vacation Rentals with Saunas in Old Saybrook, CT

Maximize your recovery with an on-site sauna, a standard feature at these premier Old Saybrook, CT vacation rentals.

Stunning House On Ct River ! - Old Saybrook, CT
9.7 71 reviews

Stunning House On Ct River !

apartment, Old Lyme
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