Old Saybrook holiday lettings

We found 492 holiday rentals — enter your dates for availability
Select from 45 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

Pool
Living area
Exterior
Living area
Exceptional
(12 reviews)

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

Orient

8% off
£9,397
for 7 nights, 1 room
£1,342 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Interior
Exterior
Room
Living area
Exceptional
(67 reviews)

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

Westbrook

7% off
£5,417
for 7 nights, 1 home
£774 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Pool
Outdoor patio fireplace, patio heaters.
Private kitchen
Basement - Full Kitchen, Pull out couch
Exceptional
(57 reviews)

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

East Haddam

7% off
£6,171
for 7 nights, 1 home
£882 per night
includes taxes & fees
Resort style getaway w/pool, spa, game room & more
Exterior
Exterior
Exterior detail
Beach
Wonderful
(59 reviews)

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

Old Lyme

8% off
£1,938
for 7 nights, 1 cottage
£277 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Living Room
Front of House
Kitchen
Side of House with outdoor shower to rinse off from the beach.
Exceptional
(11 reviews)

4 BED/2 BATH -PRIVATE BEACH: OLD COLONY

Old Lyme

7% off
£3,690
for 7 nights, 1 home
£527 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
£4,782
for 7 nights, 1 home
£683 per night
includes taxes & fees
Luxury Beach House in Giants Neck Beach - Perfect for Large Families!
Private kitchen
Terrace/patio
Living area
Exterior
Exceptional
(33 reviews)

Updated cottage "Beriozka" on Cedar Lake

Chester

7% off
£1,196
for 7 nights, 1 cottage
£171 per night
includes taxes & fees
Updated cottage "Beriozka" on Cedar Lake
Property grounds
Property grounds
Kitchen
Dining
Exceptional
(17 reviews)

Cornfield Point Cottage

Old Saybrook

8% off
£6,148
for 7 nights, 1 home
£878 per night
includes taxes & fees
Cornfield Point Cottage
Exterior detail
Living area
Outdoor dining
Dining
Exceptional
(38 reviews)

Cottage near the beach

Niantic

7% off
£1,342
for 7 nights, 1 cottage
£192 per night
includes taxes & fees
Cottage near the beach
Hall into sitting room
Master bed onto balcony
Dining room onto porch
Kitchen from dining room
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
£7,570
for 7 nights, 1 home
£1,081 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Interior
Beach
Living area
Room
Exceptional
(27 reviews)

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

Niantic

11% off
£2,233
for 7 nights, 1 home
£319 per night
includes taxes & fees
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
Living area
Winter afternoon from the boathouse
Full chef's kitchen with new appliances
Ipe deck in the morning sun
Exceptional
(6 reviews)

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

Old Lyme

16% off
£4,557
for 7 nights, 1 home
£651 per night
includes taxes & fees
Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet
Room
Beach
Interior
Living area
Exceptional
(36 reviews)

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

Niantic

11% off
£2,185
for 7 nights, 1 home
£312 per night
includes taxes & fees
PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC W/ 6 QUEENS 1 FULL BED
Room
Beach
Living area
Private kitchen
Exceptional
(32 reviews)

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

Clinton

11% off
£2,166
for 7 nights, 1 home
£309 per night
includes taxes & fees
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
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
£1,148
for 7 nights, 1 apartment
£164 per night
includes taxes & fees
The Little Chestnut. A charming historic apartment in Downtown Chester
One full bedroom w two full sleeper sofas to accommodate 4 guests comfortably.
Property grounds
Private kitchen
Private kitchen
Exceptional
(66 reviews)

Summer at the Haddam House

Haddam

8% off
£1,351
for 7 nights, 1 home
£193 per night
includes taxes & fees
Summer at the Haddam House
family room
Beautiful sun room for dining
Newly remodeled kitchen
family room
Exceptional
(27 reviews)

Make Memories in Charming Hawk's Nest Beach!

Old Lyme

8% off
£1,949
for 7 nights, 1 home
£278 per night
includes taxes & fees
Make Memories in Charming Hawk's Nest Beach!
Front entrance door
Open living room, dining room, and kitchen area
Front of cottage
Kitchen nook, laptop workstation
Exceptional
(8 reviews)

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

Waterford

7% off
£2,566
for 7 nights, 1 home
£367 per night
includes taxes & fees
Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street
Beach
Exterior
Exterior detail
Living area
Exceptional
(55 reviews)

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

Old Lyme

8% off
£1,526
for 7 nights, 1 cottage
£218 per night
includes taxes & fees
2Bdr Beachfront; 11B second floor, Old Colony Beach , CT
Dining
Exterior
Living Room with view of expandable dining table
Loft View of Living Room
Exceptional
(91 reviews)

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton

7% off
£1,068
for 7 nights, 1 cottage
£153 per night
includes taxes & fees
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Seat 6 people at the dining table, or use it to get some work done.
Enter into the open floor plan with updated kitchen, living, and family room.
Chef's kitchen with cooking supplies, large island, and ample cabinet space.
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
£2,494
for 7 nights, 1 home
£356 per night
includes taxes & fees
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
Cute town at night - Little House Brewery
Dining
Living area
Take your morning coffee by the waterfall
Exceptional
(26 reviews)

The Millhouse Downtown Chester

Chester

8% off
£1,966
for 7 nights, 1 apartment
£281 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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Old Saybrook

  • Scenic Beaches: Enjoy the picturesque Connecticut shoreline, perfect for relaxing walks and sunbathing.
  • Historic Landmarks: Discover the rich history of Old Saybrook through its charming historic sites and the Old Saybrook Centre.
  • Tranquil Parks: Explore beautiful urban parks that offer serene spaces for picnics and leisurely strolls.
  • Saybrook Point: Experience the tranquil beauty of Saybrook Point, ideal for waterfront activities and community events.
  • Cozy Accommodations: Choose from a variety of charming vacation rentals, including cottages and private homes, for a delightful stay.

Popular types of accommodation in Old Saybrook

Welcome to Old Saybrook, Connecticut, a charming coastal town rich in history and natural beauty. Here, you can explore picturesque beaches, historic landmarks, and scenic parks. Popular accommodation options include houses, cosy cottages, and comfortable apartments, ensuring a delightful stay. Whether you're seeking a serene retreat or an adventurous getaway, Old Saybrook's vacation rentals provide the perfect base to discover its unique attractions and experiences.

  • Houses: The top choice for visitors in Old Saybrook, offering spacious and comfortable living for families and groups.
  • Cottages: Quaint and charming, these provide a perfect escape for a peaceful retreat amidst nature.
  • Apartments: Conveniently located, apartments offer a home-like atmosphere ideal for short or extended stays.
  • Condos: A popular option for those seeking modern amenities and community facilities.
  • Villas: Luxurious and spacious, villas are perfect for a lavish getaway with stunning views.**

Top attractions in and around Old Saybrook

Old Saybrook, Connecticut, offers a charming seaside escape perfect for outdoor enthusiasts and romantics alike. Explore the scenic beaches, visit urban parks, and experience the tranquil beauty of Saybrook Point. Enjoy leisurely strolls along the waterfront or engage in local meetups to immerse yourself in the community's culture. Whether you're seeking relaxation or adventure, Old Saybrook promises a delightful getaway for all types of travellers.

  • Harvey's Beach: A serene beach located within Old Saybrook, offering a relaxed atmosphere perfect for sunbathing and swimming. Its gentle waves and sandy shores make it an ideal spot for families and relaxation.
  • Hammonasset Beach State Park: A stunning state park renowned for its scenic views and outdoor adventures, featuring miles of coastline perfect for hiking, picnicking, and wildlife watching.
  • Orient Point County Park: A family-friendly urban park that combines city vibes with outdoor activities, offering playgrounds, picnic areas, and trails for leisurely walks amidst natural beauty.

Things to do recommended for couples

For a romantic getaway in Old Saybrook, explore the quaint waterfront and share a sunset picnic at Saybrook Point. Enjoy a leisurely stroll along the beach, or indulge in a candlelit dinner at a charming local restaurant, where exquisite cuisine complements the intimate atmosphere.

Things to do recommended for families

Families visiting Old Saybrook can enjoy a delightful day at the renowned Saybrook Point Park, perfect for picnics and nature walks. Children will love the fun activities at the nearby Childrens Museum of Southeastern Connecticut, where learning meets play in a captivating environment.

Things to do recommended for groups

Groups visiting Old Saybrook can experience the thrill of motor racing at Waterford Speedbowl, located 21km away. This venue offers an exhilarating atmosphere perfect for those seeking adventure and excitement in the heart of Connecticut.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Old Saybrook

When travelling with a group, family, or pets, or if you're considering extended stays, it's important to apply the right filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Old Saybrook with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Old Saybrook with young kids: Travelling with young children can present some challenges. It's important to prioritise their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Old Saybrook: For many, a family holiday wouldn’t feel whole without their furry companion by their side. If this resonates with you, explore Vrbo accommodations that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Old Saybrook: If you’re seeking holiday rentals with discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Old Saybrook

Old Saybrook, Connecticut, is a charming destination perfect for a relaxing getaway. Explore the scenic Connecticut shoreline, where you can enjoy picturesque views and tranquil walks. The historic Old Saybrook Centre offers a glimpse into the town's rich past, while the inviting atmosphere of South Cove is ideal for family-friendly excursions. Don't miss the chance to unwind by a fireplace and soak in the romantic vibes that this delightful city has to offer.

  • Westbrook: Located a mere 6km from Old Saybrook, Westbrook is a charming coastal town renowned for its stunning outdoor scenery and romantic settings. Visitors can indulge in a variety of activities, from relaxing at local resorts to enjoying live music concerts. The beautiful beaches, including family-friendly options, provide the perfect backdrop for a day of sun and sand. Westbrook also boasts excellent golf courses and event venues, making it an ideal spot for both leisure and special occasions.
  • Old Lyme: Just 5km away from Old Saybrook, Old Lyme offers a delightful mix of outdoor adventure and scenic beauty. This quaint town is a haven for nature lovers, with its picturesque landscapes and recreational areas perfect for hiking and mini golf. Families can enjoy the sandy shores of nearby beaches, while the nearby national state park invites exploration and discovery. Old Lyme's tranquil atmosphere makes it a perfect destination for those seeking relaxation amidst nature's splendour.
  • Greenport: Situated 21km from Old Saybrook, Greenport is a delightful beach town that combines outdoor activities with a romantic coastal vibe. Here, visitors can explore beautiful beaches and parks while enjoying the area's vibrant recreational offerings, including golf courses and music concerts. Greenport's laid-back charm and stunning waterfront views make it an ideal spot for leisurely strolls and sunset watching, providing a perfect escape for those looking to unwind by the sea.

Best time to go to Old Saybrook

If you're planning a trip to Old Saybrook, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnyLowModerately Low
February32.4°F (0.2°C)Light RainMostly SunnyLowModerately Low
March38.5°F (3.6°C)Light RainMostly SunnyLowModerately Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June66.4°F (19.1°C)Light RainMostly SunnyHighModerately High
July73.8°F (23.2°C)Light RainMostly SunnyHighModerately High
August72.7°F (22.6°C)Light RainMostly SunnyHighModerately High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
November45.5°F (7.5°C)Light RainMostly SunnyAverageAverage
December37.8°F (3.2°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you eager to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated area for you to plan new trips, manage ongoing arrangements, or review and organise your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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 most popular type of holiday rental accommodation in Old Saybrook?
According to our data, houses are the most desirable type of holiday rental in Old Saybrook. But that goes without saying, everyone's idea of the perfect trip differs. Vrbo has holiday homes of all sizes and shapes, and we'll help you find the perfect match.
How much does it cost to rent a holiday rental in Old Saybrook?
Property type, length of stay and time of year are some factors that can determine the price of a holiday home. Simply click on your dates of travel to find the ultimate escape. From homey country cottages to plush villas, all Vrbo holiday rentals provide incredible value.
How much does it cost to rent a beach house in Old Saybrook?
When you travel and the style and size of the property will influence the cost of your beachside holiday rental. Click on your Old Saybrook travel dates to view your available options on Vrbo. Can't live without a hot tub? Use the filters to pick the features and amenities you need.
Are there pet-friendly holiday rentals in Old Saybrook?
There certainly are. You can pick from 34 holiday homes that welcome pets in Old Saybrook on Vrbo. Our furry companions deserve a getaway too, so simply use our search function for pet-friendly holiday rentals to book a property where your puppy dog can join in the fun.
Can I rent a house with a pool in Old Saybrook?
Check the "pool" box in our filter tool and you'll find two houses with private pools in Old Saybrook on Vrbo. Lazy soak or races and ball games? Free time is up to you when your holiday property comes with a swimming pool.
What are popular rental amenities in Old Saybrook?
Some of the most popular rental amenities people are looking for in Old Saybrook include a garden, a fireplace and a nearby waterfront. Whether you're on the road with family, pals or even pets, Vrbo holiday homes include the best amenities for beginning new traditions with the people you love.
Are there large group holiday rentals in Old Saybrook?
With four holiday rentals that can sleep 10 or more guests in Old Saybrook, there's no need to keep your invite list short. From fun family get-togethers to special events like birthday and Christmas parties, Vrbo can help you find a large group rental that fits the occasion.
Are there holiday rentals in Old Saybrook that welcome kids?
Old Saybrook has 34 family-friendly holiday rentals to pick from. And securing a stay that welcomes kids is a cinch with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll get conveniences and perks such as living rooms, kitchens and pools.
What are the top attractions for families in Old Saybrook?
There's a ton of awesome things to see and do with the family in Old Saybrook, such as:
  • Essex Steam Train
  • Harveys Beach
  • Clinton Town Beach
Can I find two-bedroom holiday rentals in Old Saybrook?
Old Saybrook has five two-bedroom properties for you to pick from. Go for a holiday home with all the space and privacy you're looking for at a price that's hard to resist on Vrbo.
Are there holiday rentals with WiFi in Old Saybrook?
Old Saybrook has 19 holiday rentals with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with your family to posting pics on social media, these Vrbo homes make it easy to go online.
How can I find holiday rentals with air conditioning in Old Saybrook?
Pick your travel dates and then make use of the filters to locate holiday rentals with air conditioning in Old Saybrook on Vrbo. With 30 air-conditioned properties on offer here, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday rental in Old Saybrook?
The minimum age is generally 16, 18 or 21. It can differ across properties on Vrbo, so check the rules of your chosen Old Saybrook stay before booking your stay.
How long can I rent a holiday rental in Old Saybrook for?
The amount of time you can stay in an Old Saybrook holiday home for is down to the property. Just put in your preferred travel dates to browse options that offer extended stays. They come with all you require to make your extended getaway more convenient and enjoyable, such as air conditioning and kitchens. Some holiday homes may also offer weekly or monthly discounts, so you can have a longer stay for less.

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