Best Holiday rentals and Airbnb offers in Old Saybrook, CT
10 5 reviews
Old Saybrook, CT
03/07 – 06/07
SG$418/nighttotal: SG$1254 (3 )
Coastal Westbrook Loft Vaulted Ceilings & Lvl 2 Ev
1 4
apartment , Westbrook
This Westbrook flat offers Mystic Harbor views and is conveniently located within 800 metres of Mystic Amtrak and 1.2 kilometres from historic downtown Mystic. This family-friendly one-bedroom flat accommodates up to four guests and features a fully equipped kitchen, air conditioning, Wi-Fi, and on-site electric vehicle charging.
Old Saybrook, CT
03/07 – 06/07
SG$2463/nighttotal: SG$7389 (3 )
Beachfront Home. Enjoyable The Blue Mermaid 3-bedroom House With Ac In Welc.
3 4
apartment , Clinton
This three-bedroom flat in Clinton offers direct ocean views and is situated 2.5 kilometres from Meigs Point Nature Centre and Hammonasset Beach State Park. This property accommodates up to six guests with three bedrooms, each containing a queen bed, and features three bathrooms, air conditioning, and Wi-Fi, making it ideal for families visiting Clinton.
10 24 reviews
Old Saybrook, CT
03/07 – 06/07
SG$685/nighttotal: SG$2055 (3 )
Mid-century Stunner With Water Views!
1 4
apartment , Essex
This split-level flat in Essex provides picturesque water views from a street within walking distance of the village, award-winning restaurants, and the historic Regent Theatre. This immaculately updated two-bedroom, two-bathroom residence accommodates up to six guests and features a fully equipped kitchen, air conditioning, a garden, and direct access to Mill Pond for fishing and kayaking, as well as a 40-acre nature preserve for hiking.
Old Saybrook, CT
03/07 – 06/07
SG$1235/nighttotal: SG$3705 (3 )
Old Lyme Pet Friendly Escape | Griswold Preserve + Beach Pass + Fireplace
3 4
apartment , Old Lyme
This Old Lyme dwelling is situated less than 1.6 kilometres from the village district and its galleries, backing onto a farm and the Griswold Preserve with walking trails. This 164 square metre residence accommodates up to six guests across three bedrooms, featuring a wood-burning fireplace, a fully equipped kitchen with a gas grill, and laundry facilities, with a garden and parking provided.
10 12 reviews
Old Saybrook, CT
02/08 – 07/08
SG$392/nighttotal: SG$1960 (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.
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.
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 2 reviews
Old Saybrook, CT
03/07 – 06/07
SG$577/nighttotal: SG$1731 (3 )
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.
9.8 25 reviews
Old Saybrook, CT
03/07 – 06/07
SG$1296/nighttotal: SG$3888 (3 )
Renovated 3br In Old Saybrook
3 4
apartment , Old Saybrook
This charming house is situated on a peaceful street in Old Saybrook, just a short walk from South Cove and a five-minute drive from the town and Harvey's beaches. The property has consistently received excellent ratings for location, cleanliness, and overall user experience. This three-bedroom home comfortably sleeps eight guests and features a modern kitchen, two bathrooms, and a private patio. Guests can enjoy a range of amenities including air conditioning, a garden, parking, high-speed Wi-Fi, and a fully equipped kitchen.
9.9 463 reviews
Old Saybrook, CT
02/08 – 07/08
SG$437/nighttotal: SG$2185 (5 )
Unique Apartment In Former Art Gallery.
1 4
apartment , Essex
This two-bedroom apartment is situated in a quiet residential neighbourhood in Essex, just a short distance from the former Erickson-Davis Gallery and a converted factory complex. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment is spacious and modern, offering 1975 square feet of living space and accommodating up to 5 guests. Amenities include a fully equipped kitchen, air conditioning, a private garden with a fire pit, a work-friendly office space, and a pet-friendly policy for an additional fee.
Old Saybrook, CT
03/07 – 06/07
SG$893/nighttotal: SG$2679 (3 )
The Nest At Black Hall
1 4
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.
Old Saybrook, CT
02/08 – 07/08
SG$797/nighttotal: SG$3985 (5 )
Cozy 2-bedroom Cape In Saybrook Center
1 4
apartment , Old Saybrook
This Old Saybrook Cape Cod-style house, situated on a quiet street within walking distance of local restaurants, shops, and a park, is approximately 3.2 kilometres from two beaches and a short drive from the Saybrook Point Resort & Spa. This two-bedroom, two-bathroom property offers guests a finished basement, large backyard ideal for outdoor activities, and sleeps up to six, with amenities including Wi-Fi, air conditioning, parking, a fitness centre, and seasonal access to bikes and paddleboards.
Best family friendly Old Saybrook, CT holiday rentals
Among the 119 accommodations in Old Saybrook, CT, here are the 4 best family friendly rentals
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.
9.2 31 reviews
Old Saybrook, CT
02/08 – 07/08
SG$389/nighttotal: SG$1945 (5 )
Woodsy Retreat With Fire Pit
1 4
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.
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
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 1 best rentals with a pool
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.
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
03/07 – 06/07
SG$576/nighttotal: SG$1728 (3 )
Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included
1 4
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.
Best Old Saybrook, CT holiday rentals with parking
10 1 review
Old Saybrook, CT
03/07 – 06/07
SG$2005/nighttotal: SG$6015 (3 )
Old Saybrook Waterfront Luxury Cornfld Point
1 4
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.
Old Saybrook, CT
03/07 – 06/07
SG$696/nighttotal: SG$2088 (3 )
Olde Lyme Coastal Farmhouse
5 4
apartment , Old Lyme
This Old Lyme residence is located near Rocky Neck State Park and Beckett Hill State Park, with The Book Barn and the Children's Museum of Southeastern Connecticut also within easy reach. This five-bedroom house accommodates up to ten guests and offers air conditioning, internet, and allows pets.
9.1 38 reviews
Old Saybrook, CT
03/07 – 06/07
SG$578/nighttotal: SG$1734 (3 )
Peace Barn In The Heart Of The Ct River Valley
5 4
apartment , Deep River
The Peace Barn is a charming, rustic retreat located in Deep River, Connecticut, just a short distance from the Connecticut River and local state parks. This studio apartment is highly rated for its location, cleanliness, and overall experience, with guests consistently praising its peaceful atmosphere. This self-catering property can accommodate up to 8 guests, offering a comfortable and spacious living area with a fully equipped kitchen. Guests can enjoy a range of amenities, including Wi-Fi, a TV for DVDs, and a private garden with hiking trails, a camping area, and a gazebo.
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.