Best Holiday rentals and Airbnb offers in Old Saybrook, CT
8.6 4 reviews
Old Saybrook, CT
20/08 – 25/08
SG$535/nightTotal: SG$2675 (5 )
Storybook Cottage
3 4
apartment , Old Saybrook
This Old Saybrook holiday home is situated within 3.2 kilometres of the Connecticut Valley Railroad State Park Trail, Essex Saybrook Antique Village Shopping Centre, and Yale New Haven Health Old Saybrook Medical Centre. The three-bedroom property sleeps six guests and boasts a fully equipped kitchen, free Wi-Fi, air conditioning, parking, and barbecue facilities, perfect for exploring Old Saybrook and its surroundings.
Old Saybrook, CT
02/08 – 07/08
SG$681/nightTotal: SG$3405 (5 )
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.
Old Saybrook, CT
25/06 – 29/06
SG$508/nightTotal: SG$2032 (4 )
Charming 1-bedrm Unit With Wifi, Ac In Quaint Deep River- Queen Of The Valley
1 2
apartment , Deep River
This Deep River apartment, situated in Deep River Centre, is within walking distance of the town's Main Street and a short drive from attractions such as Gillette Castle and the Essex Steam Train. The one-bedroom, two-bathroom dwelling offers WiFi, a dishwasher, and a private back deck; it sleeps two guests and is conveniently located for exploring nearby Chester and Essex.
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.
9.5 4 reviews
Old Saybrook, CT
01/08 – 03/08
SG$528/nightTotal: SG$1056 (2 )
Charming Pied A Terre
1 2
apartment , Old Lyme
This Old Lyme apartment rental is situated on Main Street within the Historic District, offering easy walking access to shops, the Old Lyme library, and the Old Lyme Ferry. The one-bedroom flat sleeps two guests and includes a kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and a garden.
9.9 186 reviews
Old Saybrook, CT
02/08 – 07/08
SG$1163/nightTotal: SG$5815 (5 )
River Barn, Sidewalk Stroll Into Essex Village
2 4
farm , Essex
The River Barn is situated in the charming village of Essex, Connecticut, a short distance from the Essex Steam Train & Riverboat and the Connecticut River. This property has consistently received excellent ratings for its location, cleanliness, and overall experience. The converted barn offers a unique and comfortable stay for up to four guests. It features a fully equipped kitchen, a dedicated office space, a private fenced-in yard with a deck and fire pit, and a range of amenities including high-speed internet, organic toiletries, and local coffee.
10 4 reviews
Old Saybrook, CT
01/08 – 03/08
SG$1027/nightTotal: SG$2054 (2 )
Modern Luxury Meets Antique Elegance.
1 2
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.
10 12 reviews
Old Saybrook, CT
20/08 – 25/08
SG$395/nightTotal: SG$1975 (5 )
Quintessential Essex. Steps From The Steam Train!
1 4
apartment , Essex
This two-bedroom flat is situated in central Essex, offering convenient access to local eateries such as Sayulitas and the Cheese Shop of Centerbrook, with Essex Village, Ivoryton Playhouse, and the CT Shoreline less than 3 kilometres away. This apartment accommodates up to five guests, featuring air conditioning, Wi-Fi, a modern kitchen with stainless steel appliances and granite countertops, a sunroom with views of the Essex Steam Train, and parking.
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 61 reviews
Old Saybrook, CT
01/08 – 03/08
SG$1006/nightTotal: SG$2012 (2 )
Stunning House On Ct River !
1 2
apartment , Old Lyme
This apartment is situated on the Connecticut River waterfront in Old Lyme, just a short drive from charming shops, restaurants, and the Mohegan Sun Casino. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. It boasts a spacious outdoor area with a deck, a private gazebo, and direct access to a public kayak launch, perfect for exploring the river.
9.9 23 reviews
Old Saybrook, CT
25/06 – 29/06
SG$459/nightTotal: SG$1836 (4 )
Remodeled Cozy Home Near Beach
1 2
apartment , Westbrook
This Westbrook, Connecticut holiday home is situated 0.6km from Westbrook Beach and the Westbrook Elks Club, offering easy access to local restaurants and shops. The newly remodelled property boasts a queen-size bedroom, large kitchen, living room, dining room, sitting area, in-house laundry, hot tub, Weber grill, and bikes; sleeping two guests comfortably.
9.8 22 reviews
Old Saybrook, CT
01/08 – 03/08
SG$531/nightTotal: SG$1062 (2 )
Adorable Cottage, 5 Min Walk To Water & Coffee
1 2
house , Westbrook
This Westbrook, Connecticut coastal property is a short walk from Westbrook Beach. The recently renovated house offers two bedrooms, one bathroom, sleeps four, includes Wi-Fi, parking, and an outdoor fire pit; a second unit is available for larger groups.
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 2 reviews
Old Saybrook, CT
02/08 – 07/08
SG$493/nightTotal: SG$2465 (5 )
The Westbrook Anchor – 1st Floor 2br W/ Ev Charger
1 4
apartment , Westbrook
This two-bedroom flat in Mystic Harbor Landing offers water views of Mystic Harbor and is a 10-minute walk (approximately 0.8 kilometres) from Mystic Amtrak station and a 15-minute walk (approximately 1.2 kilometres) to the historic downtown area. This family-friendly apartment accommodates up to four guests and features a fully renovated kitchen with an island, air conditioning, Wi-Fi, and EV charging, situated in a neighbourhood ideal for exploring local beaches and enjoying a peaceful stay.
Old Saybrook, CT
01/08 – 03/08
SG$560/nightTotal: SG$1120 (2 )
Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included
1 2
apartment , Westbrook
This Westbrook flat is centrally located in Westbrook Centre, a four-minute drive from West Beach and less than 1 kilometre from the Westbrook Outlets. This one-bedroom, 50-square-metre flat accommodates up to four guests and features a Level 2 EV charger, off-street parking, air conditioning, a kitchen with a fridge, microwave, and dishwasher, and a spacious living area with a 55-inch television.
10 20 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.
Old Saybrook, CT
02/08 – 07/08
SG$514/nightTotal: SG$2570 (5 )
Peace Barn
1 4
apartment , Deep River
This Deep River farm, perfect for families, offers five bedrooms, two bathrooms, and sleeps eight guests; further details regarding its precise location within Deep River are needed to specify proximity to local attractions. The property includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, Wi-Fi, parking, and a garden, ensuring a comfortable stay.
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 67 reviews
Old Saybrook, CT
20/08 – 25/08
SG$894/nightTotal: SG$4470 (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.
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.
9.9 41 reviews
Old Saybrook, CT
25/06 – 29/06
SG$275/nightTotal: SG$1100 (4 )
Quiet Setting For This Guesthouse With Pool.
1 2
house , Old Lyme
This charming guest house is situated on a quiet street, just a short drive from the picturesque town of Old Lyme and its beautiful beaches. It has received excellent ratings for location, cleanliness and overall experience. The self-contained accommodation comfortably sleeps two guests and features a queen-size pull-out bed, a refrigerator, microwave, and a Keurig coffee machine. Guests can enjoy the refreshing swimming pool, relax in the outdoor lounging area, or explore the nearby towns of Essex, Old Saybrook, and Chester.
9.7 38 reviews
Old Saybrook, CT
25/06 – 29/06
SG$720/nightTotal: SG$2880 (4 )
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.
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
Old Saybrook, CT
25/06 – 29/06
SG$669/nightTotal: SG$2676 (4 )
The Nest At Black Hall
1 2
apartment , Old Lyme
This Old Lyme studio apartment is situated on the waterfront, 0.5 kilometers from the Florence Griswold Museum and the Connecticut Valley Railroad State Park Trail, and adjacent to a golf course. This 88 square meter flat offers accommodation for up to four guests with air conditioning, internet, and a terrace, providing direct access to waterfront activities like kayaking and scuba diving.
9.9 73 reviews
Old Saybrook, CT
20/08 – 25/08
SG$569/nightTotal: SG$2845 (5 )
Downtown Essex Apartment - Steps To River!
1 4
apartment , Essex
This one-bedroom flat is conveniently located in Downtown Essex, just a short walk from the river and within easy reach of shops, restaurants, and local attractions. The property has received excellent ratings for its location, cleanliness, and overall experience. The 84 square metre flat comfortably accommodates up to four guests and features a fully equipped kitchen, a private balcony, air conditioning, free Wi-Fi, and a washing machine. Guests can enjoy river views, prepare meals, relax on the balcony, and explore the charming town of Essex.
9.8 138 reviews
Old Saybrook, CT
02/08 – 07/08
SG$1142/nightTotal: SG$5710 (5 )
Authentic 1795 Historic Homestead W/ Private Grounds For Gatherings And Retreats
5 4
apartment , Old Saybrook
This five-bedroom home is situated in the Saybrook Manor neighbourhood of Old Saybrook, a short drive from the Boston Post Road and close to beaches, restaurants, casinos, and attractions. It has received excellent user ratings. The apartment spans 325 square metres and comfortably accommodates up to 14 guests. It features a fully equipped kitchen, a spacious garden, a spa, a terrace, and parking.
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
9.0 2 reviews
Old Saybrook, CT
25/06 – 29/06
SG$957/nightTotal: SG$3828 (4 )
Fenwood Coastal Getaway Private Beach Access
3 2
apartment , Old Saybrook
This Old Saybrook seaside property is located within 5km of Harvey's Beach and under 10km from Saybrook Country Barn, offering easy access to both the coast and local attractions like the General William Hart House and Katharine Hepburn Cultural Arts Center. The three-bedroom, three-bathroom house sleeps six guests and includes a fully equipped kitchen, laundry facilities, a private fenced garden, and parking; enjoy stunning ocean views and the convenience of nearby amenities.
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.
10 1 review
Old Saybrook, CT
02/08 – 07/08
SG$722/nightTotal: SG$3610 (5 )
Old Lyme Pet Friendly Escape | Griswold Preserve
3 4
apartment , Old Lyme
This three-bedroom, two-bathroom holiday cottage in Old Lyme offers accommodation for up to six guests, situated less than 1 kilometre from the Old Lyme galleries and village district, and adjacent to the Griswold Preserve with its walking trails. Guests can enjoy a spacious garden with outdoor seating and a gas grill, a real wood-burning fireplace, a fully equipped kitchen with a dishwasher and microwave, and an in-unit washer and dryer, all within a peaceful setting.
9.6 101 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.