Best Holiday rentals and Airbnb offers in Old Saybrook, CT
9.9 34 reviews
Old Saybrook, CT
20/08 – 25/08
SG$425/nighttotal: SG$2125 (5 )
Barn At Ashlawn Farm (On 110 Acres)
2 4
gîte , Lyme
This charming cottage is situated on a working farm in the Lyme countryside, just a short distance from the historic Bill Hill road, offering a peaceful escape from the hustle and bustle. The property has received excellent reviews for its cleanliness, location, and overall experience. The two-bedroom cottage comfortably sleeps five guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher. Enjoy the fresh air and stunning views of the surrounding countryside from the private outdoor area, while interacting with friendly farm animals and exploring the surrounding area.
9.6 8 reviews
Old Saybrook, CT
25/06 – 29/06
SG$1080/nighttotal: SG$4320 (4 )
Charming Year-round Beach Home In Indian Town, Old Saybrook
3 2
apartment , Old Saybrook
This Saybrook Manor holiday home in Old Saybrook, Connecticut is situated within 3.2km of Chalker Beach, the Katharine Hepburn Cultural Arts Center, and the General William Hart House. This three-bedroom, two-bathroom property boasts 177 square metres of living space, sleeping up to eight guests and offering amenities including a Jacuzzi, terrace, garden, and parking, plus a fully equipped kitchen and in-house laundry facilities.
9.8 206 reviews
Old Saybrook, CT
20/08 – 25/08
SG$362/nighttotal: SG$1810 (5 )
Historic Essex Home W/ Large Yard Near Downtown!
2 4
house , Essex
This charming Essex house is situated just 16 kilometres from the Goodspeed Opera House and 34 kilometres from Wesleyan University, offering a peaceful retreat in a quiet neighbourhood close to the town centre. The property has received excellent ratings for location, cleanliness, and overall user experience, making it a popular choice for travellers. This 2-bedroom property, spanning 130 square metres, comfortably accommodates up to 4 guests. The house features a fully equipped kitchen, a spacious living area, a private garden, a spa, and parking, offering a range of amenities and activities for a relaxing and enjoyable stay.
Old Saybrook, CT
27/06 – 04/07
SG$450/nighttotal: SG$3150 (7 )
The Rudder At Soundview · Beach+ocean+sunrise
1 2
apartment , Old Lyme
The Rudder at Soundview apartment is a self-catering flat located in a rural part of Old Lyme, Connecticut, close to Ocean Beach Park and a short drive from attractions such as The Book Barn and the Children's Museum of Southeastern Connecticut. This 23-square-metre (approximately 248 square feet) one-bedroom apartment sleeps two guests and features direct beach access, high-speed Wi-Fi, a fully equipped kitchen, air conditioning, a smart TV, and proximity to various water sports.
Old Saybrook, CT
20/08 – 25/08
SG$454/nighttotal: SG$2270 (5 )
Coastal Getaway|7 Min Walk To Beach|parking|a/c
1 4
apartment , Westbrook
This two-bedroom flat in Westbrook offers proximity to the town's shops and restaurants, with Westbrook Town Beach a 4-minute drive away and Hammonasset State Park 16 minutes distant. This accommodation for four guests features a microwave, dishwasher, air conditioning, and on-site laundry, providing a convenient base for exploring the shoreline.
10 1 review
Old Saybrook, CT
25/06 – 29/06
SG$1642/nighttotal: SG$6568 (4 )
Evertide | Walk To Saybrook Point Resort + Main St
1 2
apartment , Old Saybrook
Evertide, a spacious five-bedroom flat in Old Saybrook, is situated 800 metres from Saybrook Point Resort & Marina and within easy walking distance of Main Street's shops and restaurants, as well as South Cove. This pet-friendly property accommodates up to fifteen guests, offering amenities such as a gas grill, a propane fire pit, and private parking for six to eight vehicles, with a washer/dryer conveniently located on the first floor.
9.8 19 reviews
Old Saybrook, CT
25/06 – 29/06
SG$268/nighttotal: SG$1072 (4 )
The Ingham Guest House-quaint & Quiet, Near Beach
1 2
cabin , Old Saybrook
The Ingham Guest House is located just 0.4 kilometres from the beaches and Main Street in Old Saybrook, offering a peaceful retreat in a quiet neighbourhood with historical significance. The property has received excellent ratings for its cleanliness, location, and overall user experience. This charming one-bedroom cottage can accommodate two guests and features a spacious living area with a full kitchen and bathroom. Guests can enjoy amenities such as free on-site parking, air conditioning, and a garden, as well as easy access to local attractions and activities.
10 45 reviews
Old Saybrook, CT
02/08 – 07/08
SG$871/nighttotal: SG$4355 (5 )
Adorable Ranch In Beach Community
4 4
apartment , Old Saybrook
This ranch-style property is located in Old Saybrook's Knollwood Beach area, just 160 metres from the Long Island Sound and a short distance from the General William Hart House. This four-bedroom dwelling accommodates up to four guests and offers private beach access to Knollwood Beach, along with a garden, parking, and proximity to local amenities including tennis and basketball courts, all within 500 metres.
8.8 1341 reviews
Old Saybrook, CT
02/08 – 07/08
SG$1307/nighttotal: SG$6535 (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 Clinton Crossing Premium Outlets, Hammonasset Beach State Park, and the Clinton Country Club. The resort has received very good user ratings, with excellent marks for location and cleanliness. The hotel offers a range of facilities, including a spa, indoor and outdoor swimming pools, tennis courts, a fitness centre, and a restaurant and bar. Guests can enjoy direct access to the beach, scenic ocean views, and comfortable rooms with modern amenities.
10 4 reviews
Old Saybrook, CT
02/08 – 07/08
SG$895/nighttotal: SG$4475 (5 )
Modern Luxury Meets Antique Elegance.
1 4
apartment , Essex
This luxurious Essex house, located in the historic Essex village, is within walking distance of restaurants, shops, and the Connecticut River Museum. Sleeping six guests across three bedrooms and two bathrooms, this tastefully remodelled period property boasts a high-end kitchen with Wolf stove and marble counters, two gas fireplaces, a private garden with hydrangeas, and parking; nearby attractions include hiking trails and the Connecticut River.
This unique floating B&B is a 44ft Lagoon Catamaran, moored in Westbrook, offering a truly unforgettable experience. It's just a short distance from the charming downtown area, perfect for exploring the local shops and restaurants. The B&B has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This luxurious vessel features three private cabins, each with a double bed and en-suite bathroom, accommodating up to six guests. The catamaran offers a spacious living area, a well-equipped kitchen, and comfortable outdoor areas perfect for relaxing and enjoying the stunning views. Guests can also enjoy personalized sailing adventures with an experienced captain, exploring the beautiful coastline and engaging in activities like swimming, snorkeling, or fishing.
10 22 reviews
Old Saybrook, CT
25/06 – 29/06
SG$885/nighttotal: SG$3540 (4 )
4 Bedrooms Modern Home With Water View & Access
1 2
apartment , Essex
This Essex farmhouse, situated near Essex Village, offers a peaceful retreat minutes from several nature trails and Mill Pond. The property boasts four bedrooms sleeping eight, a dedicated movie room, outdoor deck, and outdoor shower; amenities include Wi-Fi, parking, and a fully equipped kitchen.
Best family friendly Old Saybrook, CT holiday rentals
Among the 119 accommodations in Old Saybrook, CT, here are the 4 best family friendly rentals
10 1 review
Old Saybrook, CT
01/08 – 03/08
SG$2091/nighttotal: SG$4182 (2 )
Old Saybrook Waterfront Luxury Cornfld Point
1 2
apartment , Old Saybrook
This luxurious waterfront house in Old Saybrook, Connecticut, boasts breathtaking Long Island Sound sunset views and is conveniently located near Old Saybrook's town centre and beaches, though precise distances aren't specified. Sleeping up to ten guests in five bedrooms with three bathrooms and a gourmet kitchen including a dishwasher, this property offers a Walpole outdoor shower, air conditioning, a garden, and internet access, plus weekly cleaning and all linens provided.
9.8 28 reviews
Old Saybrook, CT
25/06 – 29/06
SG$807/nighttotal: SG$3228 (4 )
Newly Renovated Beach Home In Cornfield Point.
3 2
apartment , Old Saybrook
This newly renovated beach house is located in Cornfield Point, a quiet neighbourhood in Old Saybrook, just 400 metres from the beach. The property has received excellent ratings for location, cleanliness and overall user experience. The house has three bedrooms and one bathroom, accommodating up to eight guests. The fully equipped kitchen, large patio, and fire pit offer everything you need for a comfortable and enjoyable stay.
9.6 102 reviews
Old Saybrook, CT
20/08 – 25/08
SG$1104/nighttotal: SG$5520 (5 )
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
3 4
cottage , Old Saybrook
Cove Street Cottage is a charming holiday home in Old Saybrook Center, just a short walk from the Saybrook Point Resort and Marina, and a short drive from beaches, shops, and historic sites. The cottage has received excellent reviews for its location, cleanliness, and overall experience. The cottage is spacious, offering 121 square metres of living space and can comfortably accommodate up to six guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, and access to the nearby resort's spa.
9.2 31 reviews
Old Saybrook, CT
06/08 – 09/08
SG$414/nighttotal: SG$1242 (3 )
Woodsy Retreat With Fire Pit
1 2
apartment , Westbrook
This apartment is located just a few kilometres from Westbrook Town Beach and offers a tranquil escape from city life, situated in a peaceful setting close to the Connecticut shoreline. It has consistently received excellent ratings for its cleanliness, location and overall user experience. The property has two bedrooms and two bathrooms, comfortably accommodating up to five guests. Enjoy a range of amenities, including a private patio with a fire pit, access to a pool and jacuzzi, a fenced-in yard, and an Italian pizza oven, along with optional add-ons like a Mercedes Sprinter Limo van, bird watching tours, and Champagne & chocolate tastings.
Best Old Saybrook, CT holiday rentals with a pool
Among the 119 accommodations in Old Saybrook, CT, here are the 4 best rentals with a pool
10 1 review
Old Saybrook, CT
25/06 – 29/06
SG$2201/nighttotal: SG$8804 (4 )
Private 2-acre Coastal Compound With Pool•cottage
1 2
apartment , Westbrook
This Westbrook apartment, a spacious Victorian beach house, is situated near Westbrook's beaches and attractions, though precise distances are unspecified. The property comprises a four-bedroom, two-bathroom main house and a separate three-bedroom cottage (available at an extra cost), accommodating up to twelve guests, and features a swimming pool and parking.
9.7 38 reviews
Old Saybrook, CT
06/08 – 09/08
SG$671/nighttotal: SG$2013 (3 )
Privateers Boathouse (Village Waterfront)
1 2
house , Essex
This waterfront cottage is located in Essex Village, a short drive from beaches, golf courses, and hiking trails. It has received excellent ratings for cleanliness, location, and overall user experience. The cottage has one bedroom and one bathroom, comfortably accommodating up to three guests. Amenities include a fully equipped kitchen, air conditioning, a private deck with water views, and access to a shared swimming pool and water activities.
10 67 reviews
Old Saybrook, CT
02/08 – 07/08
SG$899/nighttotal: SG$4495 (5 )
3br Updated Cottage W/ Pool In Old Saybrook
1 4
apartment , Westbrook
This charming cottage is located in Old Saybrook, Connecticut, just a short drive from multiple beaches and the charming towns of Old Saybrook and Mystic. The property has consistently received excellent ratings for its cleanliness, location, and overall experience. The cottage offers three bedrooms and one bathroom, comfortably accommodating up to six guests. The property features a private garden, a swimming pool, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
9.8 100 reviews
Old Saybrook, CT
06/08 – 09/08
SG$380/nighttotal: SG$1140 (3 )
Seashore Getaway - Ct Shoreline
1 2
apartment , Old Saybrook
This one-bedroom apartment is located in Old Saybrook, just a short walk from the beach and within easy reach of the train station. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment has two bathrooms and can comfortably accommodate two guests. It boasts a range of amenities including a swimming pool, fitness centre, and garden, providing plenty of opportunities for relaxation and recreation.
Frequently asked questions about holiday rentals in Old Saybrook, CT
Which walking or cycling routes are the best in Old Saybrook, CT?
The Old Saybrook Town Green is a lovely place to stroll, while the Connecticut River Trail offers a scenic bike ride along the river. For a longer ride, try the Shoreline Greenway Trail, which stretches along the coast.
What are the best Airbnb and vacation rentals in Old Saybrook, CT?
What sports or outdoor activites can visitors enjoy in and around Old Saybrook, CT?
Old Saybrook is great for outdoor activities! You can go kayaking or paddleboarding on the Connecticut River, play a round of golf at the Indian Neck Golf Course, or go for a hike in the Cockaponset State Forest.
What are the most popular Airbnbs in Old Saybrook, CT?
What other towns or cities can be easily accessed from Old Saybrook, CT?
Old Saybrook is well-positioned! You can easily reach Essex, known for its charming shops and restaurants, or head to Mystic, with its famous aquarium and maritime history.
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 typically offer amenities like WiFi, air conditioning, and laundry facilities. Many also include private decks or patios, and some even have hot tubs or swimming pools.
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 your preferences. Summer is popular for beachgoers, while autumn offers beautiful foliage and cooler temperatures. Spring and early fall are also pleasant times to visit.
What are the best rentals or Airbnbs with a jacuzzi in Old Saybrook, CT?
What are the local dishes in Old Saybrook, CT region?
The region is known for its fresh seafood, so you'll find plenty of clam chowder, lobster rolls, and grilled fish dishes. Local farms also supply fresh produce, which is used in many restaurants.
Destinations nearby
Best Old Saybrook, CT holiday rentals with a balcony
10 1 review
Old Saybrook, CT
27/06 – 04/07
SG$493/nighttotal: SG$3451 (7 )
Keel At Soundview · Beach+oceanview+sunrise
1 2
apartment , Old Lyme
This Old Lyme beachfront flat, situated in a rural area, is a short 3.2km drive from Rocky Neck State Park and 3.8km from the Lyme Academy of Fine Arts. The 50 square metre self-catering apartment sleeps two, boasting a fully equipped kitchen, air conditioning, Wi-Fi, a terrace, parking, and proximity to Ocean Beach Park and the New London Ferry Dock.
This charming cottage is located on the serene Uncas Lake in Lyme, Connecticut, just a short drive from the vibrant town centre. The cottage consistently receives excellent ratings for its cleanliness, location and overall experience. The cottage offers 204 square metres of space, comfortably accommodating up to six guests in its three bedrooms. This peaceful retreat boasts a range of amenities including a fully equipped kitchen, a spacious screened-in porch, a private garden, and complimentary watercraft for exploring the lake.
9.4 15 reviews
Old Saybrook, CT
01/08 – 03/08
SG$570/nighttotal: SG$1140 (2 )
Adorable Cottage, 5 Min Walk To Water & Town
2 2
apartment , Westbrook
This charming cottage is located in Westbrook Center, just a 1.5 kilometre walk from Middle Beach and a 6 kilometre drive from Quotonset Beach, offering easy access to the beautiful coastline. The cottage has consistently received excellent reviews from previous guests, highlighting its comfortable and convenient features. This two-bedroom property comfortably sleeps four guests, with a queen-sized bed in each bedroom and a pull-out sofa. The cottage is equipped with modern amenities, including a fully equipped kitchen, a dishwasher, free Wi-Fi, air conditioning, a jacuzzi, and a dedicated workspace, perfect for remote workers.
Old Saybrook, CT
25/06 – 29/06
SG$1889/nighttotal: SG$7556 (4 )
Tranquil Farmhouse In Charming Lyme
6 2
farm , Lyme
This Lyme farmhouse, located in a rural hamlet on the eastern Connecticut River, is 12 kilometres from the Amtrak station and within 30 minutes of New London, offering proximity to Nehantic State Forest for hiking and swimming. This 6-bedroom, 5.5-bathroom property accommodates up to 12 guests and features a terrace with views of a swimming pool and tennis court, alongside nearby access to organic produce and a community art studio.
Best Old Saybrook, CT holiday rentals with parking
Old Saybrook, CT
23/07 – 26/07
SG$742/nighttotal: SG$2226 (3 )
1st Floor Westbrook Anchor | 2 Queen Beds | Ev Charger | Near Beach
2 4
apartment , Westbrook
This ground-floor flat in Westbrook Centre offers convenient access, being a 4-minute drive from West Beach and less than 1 kilometre from Westbrook Outlets. This 50 square metre apartment sleeps up to four guests and features two bedrooms, one bathroom, a kitchen with a dishwasher, air conditioning, and dedicated parking, serving as an ideal base for exploring the shoreline.
10 3 reviews
Old Saybrook, CT
20/08 – 25/08
SG$689/nighttotal: SG$3445 (5 )
A Perfect Getaway. Direct Assess To The 1000 Acre Old Saybrook Essex Preserve
2 4
cottage , Old Saybrook
This charming cottage is situated in Essex, just a short drive from Old Saybrook's town beaches, shops, restaurants, and the Kate Cultural Arts Center. It's a peaceful location, perfect for those seeking a relaxing getaway. The cottage features two bedrooms and two bathrooms, comfortably accommodating up to four guests. It boasts a fully equipped kitchen, a private patio, a jacuzzi, and access to nearby hiking and biking trails, making it ideal for families and couples alike.
10 1 review
Old Saybrook, CT
20/08 – 25/08
SG$556/nighttotal: SG$2780 (5 )
Gorgeous 3-bedroom House In Tranquil Westbrook Perfect For Relaxing Getaway
3 4
apartment , Westbrook
This three-bedroom flat, suitable for six guests, is located in the Westbrook Centre district, offering proximity to Indian River Marina and Essex Island Marina, as well as historical attractions such as the Connecticut Valley Railroad State Park. Guests at this property can enjoy air conditioning, Wi-Fi, a kitchen equipped with a fridge and microwave oven, and access to a garden, with nearby family-friendly activities including Stay and Play LLC and Saybrook Country Barn.
Old Saybrook, CT
27/06 – 04/07
SG$608/nighttotal: SG$4256 (7 )
Stoneacre At Point O'woods
1 4
apartment , Old Lyme
This two-bedroom flat in Old Lyme offers exclusive access to the Point O' Woods beach community, providing a direct connection to the shore. This single-storey residence accommodates up to four guests, featuring a fully equipped kitchen, a living room with a gas fireplace, and accessible bathrooms, alongside a back patio with a fire table and a front deck.