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Best Vacation rentals and Airbnb offers in Old Saybrook, CT
8.8 1341 reviews
Old Saybrook, CT
08/02 – 08/07
$1017/nighttotal: $5085 (5 )
Water's Edge Resort & Spa
2 4
resort , Westbrook
Water's Edge Resort & Spa is located in Westbrook, Connecticut, just a short drive from the Clinton Crossing Premium Outlets and Hammonasset Beach State Park. The resort has received very good user ratings, with excellent scores for location and cleanliness. The resort offers a range of amenities, including a private beach, indoor and outdoor pools, a spa, a fitness center, tennis courts, and a restaurant and bar. Guests can enjoy scenic ocean views from their rooms or the resort's facilities.
10 5 reviews
Old Saybrook, CT
08/01 – 08/03
$318/nighttotal: $636 (2 )
Coastal Westbrook Loft Vaulted Ceilings & Lvl 2 Ev
1 2
apartment , Westbrook
This Mystic Harbor Landing apartment in Westbrook offers 1 bedroom and 1 bathroom, featuring breathtaking water views of Mystic Harbor and convenient access to the Mystic Amtrak station, located just 10 minutes away by foot, and the historic downtown area, a 15-minute walk. This family-friendly dwelling accommodates up to 4 guests and includes a fully equipped kitchen with a dishwasher and microwave, air conditioning, on-site parking with Level-2 EV charging, a garden, and a fitness center, all within a walking and biking-friendly neighborhood.
10 34 reviews
Old Saybrook, CT
08/20 – 08/25
$603/nighttotal: $3015 (5 )
Cornfield Point Charmer–walk To Beach
2 4
apartment , Old Saybrook
This Old Saybrook apartment is just a 400-foot walk from a beautiful spot overlooking the Long Island Sound and a 10-minute stroll from a private sandy beach. The apartment consistently receives excellent reviews for its location, cleanliness, and overall experience. The two-bedroom, one-bathroom dwelling comfortably accommodates up to four guests. The apartment boasts a fully equipped kitchen, a spacious deck with a fenced-in backyard, a grill, and bikes, offering everything you need for a relaxing and enjoyable stay.
9.6 106 reviews
Old Saybrook, CT
06/25 – 06/29
$371/nighttotal: $1484 (4 )
Storybook
2 Bedroom Cottage
1 2
apartment , Old Saybrook
This charming cottage, situated in the heart of Old Saybrook, offers a unique and unforgettable experience for travelers. Built in 1895, the cottage retains its original character while offering modern conveniences, and has been professionally redesigned by renowned designer Charles Spada, boasting antique furnishings and decor that create a storybook ambiance. With excellent user, location, and cleanliness ratings, this cottage is an ideal choice for a memorable stay. The cottage features two bedrooms and one bathroom, with additional sleeping arrangements available, accommodating up to four guests. It offers a spacious living room and master bedroom, a private backyard with beautiful stonework and plantings, and amenities such as a fully equipped kitchen, air conditioning, and internet access. Its convenient location makes it an ideal base for exploring Old Saybrook's shops, galleries, restaurants, and the picturesque Old Saybrook Town Beach, all within easy walking distance.
10 53 reviews
Old Saybrook, CT
08/20 – 08/25
$925/nighttotal: $4625 (5 )
Secret Seaside Stone Cottage
1 4
apartment , Westbrook
This Westbrook apartment is located in the marina district, directly on the Patchogue River with a private dock, and is just a walk or bike ride from the beach. The apartment has received excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment comfortably sleeps 8 guests and features a spacious layout with 3 bedrooms, 2 bathrooms, and a fully equipped kitchen. Amenities include a private dock with water access, a hot tub, a fireplace, a pool table, and beach equipment, making it perfect for both relaxing and entertaining.
10 44 reviews
Old Saybrook, CT
06/25 – 06/29
$1163/nighttotal: $4652 (4 )
Wonderful 4br Old Saybrook Beach Home!
4 2
apartment , Old Saybrook
This four-bedroom apartment in Old Saybrook is located just 150 steps from a private beach, making it perfect for families or groups seeking easy access to the sand and surf. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience. The home features a spacious layout with two full bathrooms, comfortably accommodating up to eight guests. Enjoy amenities like a private yard, a fully equipped kitchen, air conditioning, and a deck offering panoramic water views.
10 1 review
Old Saybrook, CT
06/25 – 06/29
$1712/nighttotal: $6848 (4 )
Private 2-acre Coastal Compound With Pool•cottage
1 2
apartment , Westbrook
This Westbrook vacation rental, a spacious seven-bedroom compound near the beach and other Westbrook attractions, offers a main house and a renovated three-bedroom cottage. The property features two full kitchens, two bathrooms, a private in-ground pool, parking, and accommodates up to twelve guests, making it ideal for large families or groups.
Old Saybrook, CT
06/25 – 06/29
$405/nighttotal: $1620 (4 )
Crows Nest
1 2
apartment , Essex
The Crows Nest is located in downtown Essex, just steps from the CT River Museum, the Steam Train, and a park, making it the perfect base for exploring the town's history and charm. The surrounding area is lively with bars, restaurants, and shops, offering a vibrant atmosphere. The Crows Nest is a cozy apartment with two bathrooms that can comfortably accommodate up to four guests. It features a kitchen, parking, internet access, and allows pets, making it ideal for a relaxing getaway.
10 28 reviews
Old Saybrook, CT
08/20 – 08/25
$760/nighttotal: $3800 (5 )
Serene Waterfront Getaway 4bd/2b
1 4
apartment , Old Saybrook
This Old Saybrook waterfront home boasts four bedrooms, two bathrooms, and sleeps ten, offering private dock access and proximity to a local golf course with complimentary cart. The house includes a fully equipped kitchen with dishwasher, air conditioning, a spacious living area, and a patio perfect for enjoying sunset views over the water, plus access to nearby wildlife areas.
9.5 32 reviews
Old Saybrook, CT
08/20 – 08/25
$494/nighttotal: $2470 (5 )
Adorable Cottage With Porch, Walk To Water & Town
1 4
apartment , Westbrook
This Westbrook, CT rental is a short walk from Westbrook Beach. The two-bedroom, one-bathroom apartment sleeps four, features free Wi-Fi, driveway parking, an outdoor fire pit, and grill, and a second unit is available for larger groups.
10 5 reviews
Old Saybrook, CT
08/02 – 08/07
$1185/nighttotal: $5925 (5 )
Bird Bliss. Our Waterview Home &Deep Water Dock.
1 4
apartment , Old Saybrook
This Old Saybrook apartment rental offers three bedrooms and three bathrooms, sleeping six, and is located near Old Saybrook's beaches with private dock access (fee applies). The unit includes a fully equipped kitchen with dishwasher, air conditioning, parking, internet, and boasts abundant birdwatching opportunities from its location.
9.8 28 reviews
Old Saybrook, CT
06/25 – 06/29
$628/nighttotal: $2512 (4 )
Newly Renovated Beach Home In Cornfield Point.
3 2
apartment , Old Saybrook
This newly renovated beach house is located in the desirable Cornfield Point neighborhood, just a 4-minute walk from the beach. The property has received excellent ratings for its location, cleanliness, and overall experience. The home features three bedrooms and one bathroom, accommodating up to eight guests. Amenities include a modern kitchen with stainless steel appliances, a spacious open floor plan, a large patio with a fire pit, and a triple lot for outdoor activities.
Best Old Saybrook, CT vacation rentals with a balcony
9.4 15 reviews
Old Saybrook, CT
08/01 – 08/03
$443/nighttotal: $886 (2 )
Adorable Cottage, 5 Min Walk To Water & Town
2 2
apartment , Westbrook
This charming cottage is located in Westbrook Center, just a short walk from Middle Beach and a quick drive to Quotonset Beach. It has received excellent ratings from previous guests, making it a popular choice for travelers seeking a relaxing coastal getaway. The cottage comfortably accommodates up to four guests with two bedrooms and a pull-out sofa. Enjoy modern amenities, including a dishwasher, air conditioning, and a private driveway, perfect for a memorable vacation in Westbrook.
9.6 5 reviews
Old Saybrook, CT
08/20 – 08/25
$496/nighttotal: $2480 (5 )
Now With Tv - Relax In Our 3-bedroom Westbrook Cottage At West Beach
3 4
cottage , Westbrook
This Westbrook cottage is located in Westbrook Center, a short distance from the Connecticut shoreline beach, the Adam Stanton House and General Store Museum, and Connecticut Valley Railroad State Park. The cottage has received excellent user ratings, making it a popular choice for travelers seeking a comfortable and convenient stay. The cottage features three bedrooms and two bathrooms, accommodating up to eight guests in its 1000 square feet of space. The cottage offers amenities like a full kitchen, air conditioning, a terrace, a garden, and parking, as well as a full basement for additional storage or leisure.
Old Saybrook, CT
06/25 – 06/29
$1469/nighttotal: $5876 (4 )
Tranquil Farmhouse In Charming Lyme
6 2
farm , Lyme
This Lyme farmhouse is located in a rural hamlet on the eastern Connecticut River, 7.5 miles from the Amtrak station, and within driving distance of New London, New Haven, Providence, and major cities including New York City and Boston. This accommodation offers 6 bedrooms, 5 bathrooms, and sleeps 12 guests, featuring a full terrace with a pool view, an all-weather tennis court, a community art studio, and proximity to Nehantic State Forest, Saybrook Country Barn, and the Katharine Hepburn Cultural Arts Center, with organic greens available from a neighboring farm.
9.8 206 reviews
Old Saybrook, CT
08/20 – 08/25
$322/nighttotal: $1610 (5 )
Historic Essex Home W/ Large Yard Near Downtown!
2 4
house , Essex
This house is located in Essex, within a 10-minute walk of historical sites such as Connecticut Valley Railroad State Park, Essex Steam Train, and Essex Library. It has excellent user, location, and cleanliness ratings. The house has 2 bedrooms, 2 bathrooms, a kitchen with a fridge, microwave oven, dishwasher, stovetop, and a washing machine. It has a floor area of 1400 square feet and a guest capacity of 4. It also has a patio, dining area, garden, spa, parking, and air conditioning. Guests can relax in the garden, and pets are allowed.
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.
10 3 reviews
Old Saybrook, CT
06/25 – 06/29
$525/nighttotal: $2100 (4 )
A Perfect Getaway. Direct Assess To The 1000 Acre Old Saybrook Essex Preserve
2 2
cottage , Old Saybrook
This charming cottage is located just a short drive from Old Saybrook's beaches, shops, and restaurants, offering a peaceful escape in a picturesque setting. The cottage is perfect for families or small groups looking for a relaxing getaway. The two-bedroom cottage features an open floor plan with hardwood floors, a modern kitchen, and a cozy living room with a fireplace. Guests can enjoy a private patio, a jacuzzi, and access to a nearby hiking and mountain biking trail.
9.9 463 reviews
Old Saybrook, CT
08/01 – 08/03
$258/nighttotal: $516 (2 )
Unique Apartment In Former Art Gallery.
1 2
apartment , Essex
**Erickson-Davis Gallery Apartment** This unique apartment is located in a former gallery, offering a blend of modern and charming aesthetics. It has excellent user, location, and cleanliness ratings. The open loft design creates a spacious and airy atmosphere, with 1975 sq. ft. of living space for up to 5 guests. The apartment features a dedicated workspace, a fenced outdoor area with a fire pit, seating, and a hammock chair, and amenities such as a kitchen with a fridge, freezer, and microwave oven, air conditioning, and parking. It also allows well-behaved pets for an extra fee.
9.6 101 reviews
Old Saybrook, CT
08/20 – 08/25
$859/nighttotal: $4295 (5 )
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
3 4
cottage , Old Saybrook
Cove Street Cottage is a waterfront accommodation in the heart of Old Saybrook Center, offering stunning views of the Long Island Sound and the Connecticut River. Just steps away from the Saybrook Point Resort and Marina, this highly-rated cottage boasts a spacious layout with 1,300 square feet, 3 bedrooms, 2 bathrooms, and a guest capacity of 6. Guests can enjoy a fully equipped kitchen, air conditioning, a jacuzzi, a garden, parking, and resort access. The cottage also features a fenced backyard with a fire pit, and bikes and chairs for guests' convenience. Nearby activities include motor boating, rock climbing, mountain biking, and cycling.
10 1 review
Old Saybrook, CT
08/20 – 08/25
$432/nighttotal: $2160 (5 )
Gorgeous 3-bedroom House In Tranquil Westbrook Perfect For Relaxing Getaway
3 4
apartment , Westbrook
This Westbrook Center condo offers convenient access to Indian River Marina and Essex Island Marina, located just 0.5 miles away, and is within a 1-mile radius of family attractions like Stay and Play LLC and historical sites such as the Connecticut Valley Railroad State Park. This family-friendly rental sleeps six with three bedrooms, including two queen beds and a bunk bed, and features air conditioning, internet, and a kitchen with a fridge and microwave, ideal for exploring Westbrook.
Frequently Asked Questions about vacation rentals in Old Saybrook, CT
What are some interesting places to visit in or near Old Saybrook, CT?
Old Saybrook has a lot to offer! You can visit the historic Old Saybrook Lighthouse, walk along the Connecticut River at the Town Green, or explore the Saybrook Point area with its shops and restaurants. If you're looking for something a bit further out, the Mystic Aquarium and the Mystic Seaport Museum are both within a short drive.
What are the best Airbnb and vacation rentals in Old Saybrook, CT?
Which walking or cycling routes are the best in Old Saybrook, CT?
The Old Saybrook Shoreline Trail is a great option for a scenic walk or bike ride. It runs along the Connecticut River and offers beautiful views of the water. You can also try the Saybrook Point Loop, which takes you past the Saybrook Point Inn and along the waterfront.
What are the most popular Airbnbs in Old Saybrook, CT?
What sports or outdoor activites can visitors enjoy in and around Old Saybrook, CT?
Old Saybrook is a great place to enjoy the outdoors. You can go kayaking or canoeing on the Connecticut River, swimming at the Town Beach, or fishing from the pier at Saybrook Point. For a more challenging activity, try hiking at the Chatfield Hollow State Park.
What are the best vacation rentals with a pool in Old Saybrook, CT?
What amenities are commonly available in vacation rentals in Old Saybrook, CT?
Vacation rentals in Old Saybrook usually have the basics like bedrooms, bathrooms, and a kitchen. Many also offer laundry facilities, wifi, and parking. Some rentals even have private decks or patios with views of the water.
What are the best rentals for families and kids in Old Saybrook, CT?
What time of year is best to rent a vacation rental Old Saybrook, CT?
The best time to visit Old Saybrook depends on what you're looking for. Summer is the most popular time to visit, with warm weather and plenty of outdoor activities. Fall offers beautiful foliage and a more relaxed atmosphere. Spring is a great time to enjoy the outdoors before the crowds arrive, and winter offers a chance to experience Old Saybrook's charming holiday season.
What are the best rentals or Airbnbs with a jacuzzi in Old Saybrook, CT?
What are the local dishes in Old Saybrook, CT region?
Old Saybrook's local cuisine reflects its coastal location. You'll find plenty of fresh seafood, especially lobster. Try a lobster roll, a lobster bisque, or a lobster mac and cheese. Other popular dishes include clams, oysters, and fish and chips.
Destinations nearby
Best Old Saybrook, CT vacation rentals with parking
9.9 186 reviews
Old Saybrook, CT
08/02 – 08/07
$904/nighttotal: $4520 (5 )
River Barn, Sidewalk Stroll Into Essex Village
2 4
farm , Essex
The River Barn is a charming farmhouse conversion located just a short distance from the Village of Essex and its picturesque waterfront. This property has consistently earned excellent ratings for its cleanliness, location, and overall guest experience. This two-bedroom, two-bathroom farmhouse can accommodate up to four guests and features a modern kitchen, a dedicated office space with high-speed internet, a private fenced-in yard with a deck and fire pit, and luxurious amenities like organic toiletries and local coffee.
9.6 8 reviews
Old Saybrook, CT
06/25 – 06/29
$840/nighttotal: $3360 (4 )
Charming Year-round Beach Home In Indian Town, Old Saybrook
3 2
apartment , Old Saybrook
This Saybrook Manor vacation home, located in Old Saybrook, Connecticut, is within two miles of Chalker Beach, the Katharine Hepburn Cultural Arts Center, and the General William Hart House. This 1910-square-foot house features three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, a Jacuzzi, a private garden with grilling area, and in-unit laundry.
9.1 38 reviews
Old Saybrook, CT
08/02 – 08/07
$430/nighttotal: $2150 (5 )
Peace Barn In The Heart Of The Ct River Valley
5 4
apartment , Deep River
The Peace Barn is a rustic retreat in Deep River, Connecticut, close to art and culture, state parks, and the Connecticut River. This studio has excellent user, location, and cleanliness ratings. The studio can accommodate up to eight guests and has five bedrooms and two bathrooms. Enjoy a private 15-acre property with hiking trails, a camping area, a gazebo, open fields, meditation spots by the lake, and a 16x16 amphitheater.
8.6 4 reviews
Old Saybrook, CT
06/25 – 06/29
$383/nighttotal: $1532 (4 )
Storybook Cottage
3 2
apartment , Old Saybrook
This Old Saybrook house rental is conveniently located within two miles of the Connecticut Valley Railroad State Park Trail, the Essex-Saybrook Antique Village Shopping Center, and Yale New Haven Health Old Saybrook Medical Center. The three-bedroom, two-bathroom home sleeps six guests and features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, free Wi-Fi, air conditioning, parking, and outdoor barbecue grills; pets are welcome.
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.
9.7 38 reviews
Old Saybrook, CT
06/25 – 06/29
$560/nighttotal: $2240 (4 )
Privateers Boathouse (Village Waterfront)
1 2
house , Essex
This waterfront cottage is located in Essex Village, a short drive from beaches, golf courses, hiking trails, and other attractions. It has excellent user, location, and cleanliness ratings. This charming house has one bedroom, one bathroom, and can accommodate up to three guests. The house features a fully equipped kitchen, comfortable living space, a private deck with waterfront views, and access to a swimming pool and kayak/paddle board launch with advance arrangement.
10 67 reviews
Old Saybrook, CT
08/02 – 08/07
$699/nighttotal: $3495 (5 )
3br Updated Cottage W/ Pool In Old Saybrook
1 4
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.
9.9 41 reviews
Old Saybrook, CT
06/25 – 06/29
$214/nighttotal: $856 (4 )
Quiet Setting For This Guesthouse With Pool.
1 2
house , Old Lyme
This charming guest house is located on a quiet residential street in Old Lyme, just a short drive from the town center and I95. It has received excellent ratings for user experience, location, and cleanliness. The cozy guest house has one bedroom and one bathroom, comfortably accommodating two guests. It offers a private pool, a dedicated lounging area, and essential amenities like a refrigerator, microwave, and Keurig coffee maker.
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.
9.2 90 reviews
Old Saybrook, CT
08/20 – 08/25
$411/nighttotal: $2055 (5 )
Money Point Beach House- Deck+views + Beach Access
3 4
apartment , Westbrook
9.5 4 reviews
Old Saybrook, CT
06/25 – 06/29
$613/nighttotal: $2452 (4 )
Coastal 3br W/ Double Living Areas | Beach Access
1 2
apartment , Old Saybrook
10 31 reviews
Old Saybrook, CT
06/25 – 06/29
$1348/nighttotal: $5392 (4 )
Cute Westbrook Cottage With Private Beach Access
1 2
apartment , Westbrook
Old Saybrook, CT
08/20 – 08/25
$385/nighttotal: $1925 (5 )
Gorgeous 3 Bedroom House In Tranquill Westbrook.
3 4
house , Westbrook
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.
9.0 2 reviews
Old Saybrook, CT
06/25 – 06/29
$744/nighttotal: $2976 (4 )
Fenwood Coastal Getaway Private Beach Access
3 2
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.
9.6 61 reviews
Old Saybrook, CT
08/01 – 08/03
$783/nighttotal: $1566 (2 )
Stunning House On Ct River !
1 2
apartment , Old Lyme
Old Saybrook, CT
08/20 – 08/25
$1025/nighttotal: $5125 (5 )
15% Off June Booking
Boat Slips Available
9 Guests
