Old Saybrook holiday rentals

We found 492 holiday rentals — enter your dates for availability
Select from 46 homes, 23 cottages and other holiday rentals in Old Saybrook to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Old Saybrook

Showing deals for:11 Dec - 18 Dec

Dining
Living area
Exterior
Living area
Exceptional
(12 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off
AU$16,709
for 7 nights, 1 room
AU$2,387 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Pool
Outdoor patio fireplace, patio heaters.
Basement - Full Kitchen, Pull out couch
Private kitchen
Exceptional
(57 reviews)

Resort style getaway w/pool, spa, game room & more

East Haddam

8% off
AU$11,165
for 7 nights, 1 home
AU$1,595 per night
includes taxes & fees
Resort style getaway w/pool, spa, game room & more
Interior
Exterior
Dining
Living area
Exceptional
(67 reviews)

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

Westbrook

8% off
AU$9,792
for 7 nights, 1 home
AU$1,399 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Exterior
Exterior
Exterior detail
Beach
Wonderful
(59 reviews)

2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT

Old Lyme

8% off
AU$3,603
for 7 nights, 1 cottage
AU$515 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Aerial view of back deck area
Front of House
Living Room
Kitchen
Exceptional
(11 reviews)

4 BED/2 BATH -PRIVATE BEACH: OLD COLONY

Old Lyme

7% off
AU$6,858
for 7 nights, 1 home
AU$980 per night
includes taxes & fees
4 BED/2 BATH -PRIVATE BEACH: OLD COLONY
Relaxing Pond on property
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Exceptional
(9 reviews)

Luxury Beach House in Giants Neck Beach - Perfect for Large Families!

Niantic

8% off
AU$8,929
for 7 nights, 1 home
AU$1,276 per night
includes taxes & fees
Luxury Beach House in Giants Neck Beach - Perfect for Large Families!
Room
Terrace/patio
Exterior
Living area
Exceptional
(33 reviews)

Updated cottage "Beriozka" on Cedar Lake

Chester

7% off
AU$2,269
for 7 nights, 1 cottage
AU$324 per night
includes taxes & fees
Updated cottage "Beriozka" on Cedar Lake
Property grounds
Property grounds
Entryway 🐳
Dining
Exceptional
(17 reviews)

Cornfield Point Cottage

Old Saybrook

8% off
AU$11,272
for 7 nights, 1 home
AU$1,610 per night
includes taxes & fees
Cornfield Point Cottage
Outdoor dining
Living area
Exterior detail
Dining
Exceptional
(38 reviews)

Cottage near the beach

Niantic

7% off
AU$2,437
for 7 nights, 1 cottage
AU$348 per night
includes taxes & fees
Cottage near the beach
Living area
Dining
Outdoor dining
Interior
Exceptional
(10 reviews)

Cheerful 3bd Cape yards from beach/ river access

Waterford

7% off
AU$4,332
for 7 nights, 1 home
AU$619 per night
includes taxes & fees
Cheerful 3bd Cape yards from beach/ river access
Interior
Beach
Living area
Room
Exceptional
(27 reviews)

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

Niantic

11% off
AU$4,101
for 7 nights, 1 home
AU$586 per night
includes taxes & fees
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
Full chef's kitchen with new appliances
Winter afternoon from the boathouse
Ipe deck in the morning sun
Living area
Exceptional
(6 reviews)

Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet

Old Lyme

16% off
AU$8,420
for 7 nights, 1 home
AU$1,203 per night
includes taxes & fees
Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet
Dining room onto porch
Master bed onto balcony
Dining room from kitchen
Kitchen from dining room
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
AU$13,773
for 7 nights, 1 home
AU$1,968 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Room
Beach
Interior
Living area
Exceptional
(36 reviews)

PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC W/ 6 QUEENS 1 FULL BED

Niantic

11% off
AU$4,101
for 7 nights, 1 home
AU$586 per night
includes taxes & fees
PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC W/ 6 QUEENS 1 FULL BED
family room
Beautiful sun room for dining
family room
Newly remodeled kitchen
Exceptional
(27 reviews)

Make Memories in Charming Hawk's Nest Beach!

Old Lyme

8% off
AU$3,594
for 7 nights, 1 home
AU$513 per night
includes taxes & fees
Make Memories in Charming Hawk's Nest Beach!
Room
Beach
Living area
Private kitchen
Exceptional
(32 reviews)

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

Clinton

11% off
AU$4,101
for 7 nights, 1 home
AU$586 per night
includes taxes & fees
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Private kitchen
Property grounds
Room
One full bedroom w two full sleeper sofas to accommodate 4 guests comfortably.
Exceptional
(66 reviews)

Summer at the Haddam House

Haddam

8% off
AU$2,543
for 7 nights, 1 home
AU$363 per night
includes taxes & fees
Summer at the Haddam House
Room
Entrance is on the front of the building.
Living area
Living area
Exceptional
(8 reviews)

The Little Chestnut. A charming historic apartment in Downtown Chester

Chester

7% off
AU$2,178
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
The Little Chestnut. A charming historic apartment in Downtown Chester
Front of cottage
Open living room, dining room, and kitchen area
Front entrance door
Open floor plan
Exceptional
(8 reviews)

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street

Waterford

8% off
AU$4,683
for 7 nights, 1 home
AU$669 per night
includes taxes & fees
Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street
Interior
Exterior
Beach
Living area
Exceptional
(55 reviews)

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Old Lyme

8% off
AU$2,798
for 7 nights, 1 cottage
AU$400 per night
includes taxes & fees
2Bdr Beachfront; 11B second floor, Old Colony Beach , CT
Dining
Exterior
Loft View of Living Room
Living Room with view of expandable dining table
Exceptional
(91 reviews)

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton

7% off
AU$2,042
for 7 nights, 1 cottage
AU$292 per night
includes taxes & fees
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Covered patio is well lit with overhead lighting.
Enter into the open floor plan with updated kitchen, living, and family room.
Seat 6 people at the dining table, or use it to get some work done.
Gateway to tranquility at the private beach is only a 5 minute walk.
Exceptional
(82 reviews)

UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

Westbrook

8% off
AU$4,590
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
Private kitchen
Dining
Take your morning coffee by the waterfall
Cute town at night - Little House Brewery
Exceptional
(26 reviews)

The Millhouse Downtown Chester

Chester

8% off
AU$3,626
for 7 nights, 1 apartment
AU$518 per night
includes taxes & fees
The Millhouse Downtown Chester

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to scenic Old Saybrook

Enjoy the history and other features of Old Saybrook. This city is scenic and relaxing, recognised for its beaches, golfing and shopping. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Old Saybrook

Do you want to find top things to see and do in the city? Venture out of your cosy holiday rental and experience everything that Old Saybrook has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Dinosaur Place at Nature's Art (12.3 mi / 19.9 km)
  • Kontokosta Winery (12.6 mi / 20.2 km)
  • Machimoodus State Park (14.7 mi / 23.7 km)
  • Saybrook Country Barn (0.1 mi / 0.1 km)
  • Chamard Vineyards (8.7 mi / 14 km)
  • The Book Barn (8.9 mi / 14.4 km)

Exploring the beaches and other natural features in Old Saybrook

Whether you're an outdoor enthusiast or just want to take in the scenery, Old Saybrook is a great place to get outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Harvey's Beach (1.9 mi / 3 km)
  • Goose Island (3.1 mi / 4.9 km)
  • Westbrook Town Beach (4.3 mi / 7 km)
  • Rocky Neck State Beach (7.1 mi / 11.4 km)
  • Clinton Town Beach (7.7 mi / 12.3 km)
  • McCook Point Beach (9.3 mi / 15 km)

Seasonal weather averages in Old Saybrook

If you're planning a holiday around warm-weather activities, July, August, June and September are the hottest months to visit, when temperatures average 21°C.

How to get to and around Old Saybrook

The nearest airport is in New London, CT (GON-Groton - New London), located 17.3 mi (27.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Fishers Island, NY (FID-Elizabeth Field), which is 18.3 mi (29.4 km) away.

If you prefer train travel, the main station serving the city is Old Saybrook Station.

Frequently asked questions

What is the best area to stay in Old Saybrook when booking a holiday rental?
When considering the best area to stay in Old Saybrook, Connecticut, you might want to explore the charming neighbourhoods that offer a delightful blend of coastal beauty and local attractions. One particularly appealing area is along the waterfront, where you can find a variety of holiday rentals that provide stunning views of the Long Island Sound. This picturesque setting not only allows for easy access to the beach but also places you near the iconic Old Saybrook Lighthouse, a lovely spot for a leisurely stroll and superb for capturing memorable photographs.Another excellent option is the historic district, which is characterised by its quaint New England architecture and a friendly setting. Here, you'll find a number of properties that showcase the area's rich maritime heritage. This neighbourhood is conveniently located near the Katharine Hepburn Cultural Arts Centre, where you can enjoy a range of performances and events that celebrate the arts.Overall, Old Saybrook has a diverse selection of properties available for holiday rentals, suiting various tastes and preferences.
Where are the best areas for renting a beach house in Old Saybrook?
For renting a beach house in Old Saybrook, the area around the Old Saybrook Lighthouse and the stunning waterfront along Long Island Sound is highly recommended. This picturesque coastal town offers a variety of holiday rentals, many of which are situated just steps from the beach, providing breathtaking views of the water. Properties in this area typically come with amenities such as spacious decks for outdoor dining, modern kitchens, and cozy living areas, superb for families or groups looking to enjoy beachside relaxation.The charming neighbourhood of Saybrook Point is particularly appealing, as it features homes that often have private access to the beach and may include additional luxuries like hot tubs and fire pits for evening gatherings. Nearby, the Old Saybrook Historical Society and the Katharine Hepburn Cultural Arts Centre offer cultural experiences for visitors, enhancing the overall appeal of the area.Additionally, the scenic waterfront parks, such as Harvey's Beach, provide opportunities for swimming, picnicking, and beachcombing, making it a great spot for those seeking a mix of leisure and outdoor activities. Rentals in this region frequently offer added conveniences like outdoor showers, laundry facilities, and proximity to local shops and restaurants, ensuring a comfortable and enjoyable stay for beachgoers.
What is the most popular type of holiday rental accomodation in Old Saybrook?
In Old Saybrook, holiday houses are the predominant type of holiday rental, with around 152 available throughout the area. These spacious properties are typically situated in serene neighbourhoods, making them ideal for families or groups seeking a relaxing getaway. Most holiday houses come equipped with multiple bedrooms, fully furnished kitchens, and comfortable living areas, along with outdoor spaces such as decks or gardens for enjoying the pleasant Connecticut weather. Additionally, there are about 72 charming cottages scattered around the town, offering a cozier alternative with similar amenities, superb for couples or smaller families.
Are there any family house rentals in Old Saybrook?
In Old Saybrook, Connecticut, there is a wide selection of family-friendly homes available, with approximately 42 properties scattered throughout the area. This charming coastal town offers a superb blend of relaxation and adventure for families. Many of these homes boast spacious living areas, fully equipped kitchens, and outdoor spaces ideal for children to play. Visitors can also expect amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.The neighbourhoods around the Old Saybrook town centre offer easy access to beautiful beaches, including the popular Harvey's Beach, where families can enjoy sunbathing and swimming. Additionally, the nearby Saybrook Point Park provides opportunities for picnicking, walking trails, and stunning views of the Connecticut River. For those interested in history, the Old Saybrook Historical Society and the General William Hart House are also within reach, adding to the richness of the area.
Can I rent a holiday home with a pool or hot tub in Old Saybrook?
In Old Saybrook, there are several holiday homes available for rent that feature either pools or hot tubs. This picturesque coastal town, located at the confluence of the Connecticut River and Long Island Sound, offers a charming setting for travellers. Many of these properties can be found in residential neighbourhoods, providing a peaceful retreat while still being close to local attractions.Rentals often come equipped with amenities such as private swimming pools, hot tubs, spacious outdoor areas superb for gatherings, and fully equipped kitchens for self-catering. Some properties might also include features like barbecue grills and beautifully landscaped gardens, enhancing the experience of outdoor living.
Are there pet-friendly house rentals in Old Saybrook?
In Old Saybrook, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups looking to enjoy a home away from home.The area is known for its charming coastal scenery and offers easy access to various parks and outdoor spaces where pets can enjoy walks and playtime. Nearby, the Old Saybrook Town Park features beautiful green spaces and walking trails, superb for leisurely strolls with your furry companions. Additionally, the scenic views along the Connecticut River provide a lovely backdrop for outdoor activities.
Are there any remote work holiday rentals in Old Saybrook?
In Old Saybrook, Connecticut, there are numerous options for remote work holiday rentals, with around 212 available throughout the area. This charming coastal town offers a variety of properties that cater to those needing a conducive work environment. Many rentals provide essential amenities such as free Wi-Fi, allowing for seamless connectivity while you work.Properties often feature comfortable living spaces with dedicated work areas, ensuring a productive atmosphere. Additionally, many homes come equipped with full kitchens, allowing you to prepare meals during your stay. The scenic surroundings of Old Saybrook, with its picturesque beaches and quaint downtown, provide a lovely backdrop for unwinding after a day of work.Moreover, you can explore local attractions such as the historic Saybrook Point and the scenic views along the Connecticut River, making this destination ideal for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Old Saybrook?
In Old Saybrook, popular rental amenities cater to a comfortable and convenient stay. Most holiday rentals feature kitchens, allowing guests to prepare their own meals and enjoy the local produce. Many properties also include inviting decks or patios, superb for relaxing outdoors and soaking in the charming coastal atmosphere. Onsite parking is commonly available, making it easy for travellers with vehicles to explore the area. Additionally, some rentals offer blenders, ideal for whipping up refreshing smoothies or cocktails during a relaxing getaway.
When is the best time to visit Old Saybrook for a holiday rental?
The best time to book a holiday rental in Old Saybrook is during the peak season from June to August. This delightful period invites families and beach enthusiasts to relish the sunny weather and enjoy the picturesque coastline of Connecticut. July stands out as the most popular month, where vibrant activities abound, from beach outings to local festivals that bring the community together.During these summer months, you can expect warm temperatures, typically ranging from 20 to 30 degrees Celsius, making it ideal for outdoor adventures such as kayaking on the Connecticut River or simply soaking up the sun on the sandy beaches. The lively option is complemented by a variety of dining options and quaint shops, ensuring that every moment is filled with enjoyment.For those seeking a more budget-friendly option, consider visiting in November. While it's outside the busy tourist season, this month offers a tranquil experience where you can explore the charming town without the crowds. The fall foliage creates a beautiful backdrop for leisurely strolls along the waterfront.Ultimately, your choice of when to visit Old Saybrook will depend on whether you prefer the energetic summer vibe or the peaceful charm of the off-peak season.
What are the top attractions in Old Saybrook?
In Old Saybrook, visitors can discover a blend of natural beauty and historical charm. The Old Saybrook Lighthouse, also known as Saybrook Breakwater Lighthouse, is a picturesque landmark that offers stunning views of the Long Island Sound. The nearby Saybrook Point Park and Marina provides a lovely space for leisurely walks, picnics, and enjoying waterfront activities.Additionally, the town boasts the historic Goodspeed Opera House, renowned for its productions and picturesque riverside location. For those interested in nature, the nearby Cockaponset State Forest offers hiking trails and opportunities for wildlife viewing. The charming downtown area features quaint shops and restaurants, making it a delightful spot to explore local culture.
Are all fees included in the Old Saybrook holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Old Saybrook holiday homes with parking?
Stayz offers a wide selection of holiday homes in Old Saybrook with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Old Saybrook holiday homes?
You can find great discounts on holiday homes in Old Saybrook on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Old Saybrook holiday home booking on Stayz?
To find Old Saybrook holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Old Saybrook?
A long-stay holiday home in Old Saybrook is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Old Saybrook holiday home?
Book your Old Saybrook holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Old Saybrook?
Prices for holiday homes in Old Saybrook vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Old Saybrook to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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