Old Saybrook Holiday Rentals

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Holiday Rentals in Old Saybrook

Shoreline Oasis

8.8 out of 10, Excellent, (3)
"The house and town were adorable. The space was the second floor. It was clean and and comfortable. "
The price is AU$409
includes taxes & fees
21 July - 22 July
Shoreline Oasis

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

9.8 out of 10, Exceptional, (6)
"We stayed for a week and the house was perfect. Comfortable, so clean, very well stocked, really nice decor and a fantastic location. Host was very helpful and responsive. Highly recommend and we will definitely be back. "
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Entire Vacation Home in Waterford Connecticut

2.0 star property
9.0 out of 10, Wonderful, (2)
"Located so perfectly close to everything we wanted to do on vacation. The house was so clean and comfortable. Communication with the owner was A++. The neighbors were even so friendly and waving/smiling. It felt as if we were home. If we come back to that area again we hope this place will be available. "
The price is AU$854
includes taxes & fees
25 July - 26 July
Entire Vacation Home in Waterford Connecticut

Charming 2-bedroom house with WiFi, AC in lovely Waterford

10.0 out of 10, Exceptional, (1)
"The home was very clean and welcoming."
The price is AU$654
includes taxes & fees
25 July - 26 July
Charming 2-bedroom house with WiFi, AC in lovely Waterford

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

9.6 out of 10, Exceptional, (131)
"Very much enjoyed our trip! "
The price is AU$1,327
includes taxes & fees
30 July - 31 July
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is AU$1,003
includes taxes & fees
2 Aug - 3 Aug
adorable ranch in beach community

New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

8.0 out of 10, Very good, (1)
"Overall a great stay. The kids didn't want to leave and neither did we."
The price is AU$1,404
includes taxes & fees
27 July - 28 July
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

The price is AU$603
includes taxes & fees
21 July - 22 July
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

9.8 out of 10, Exceptional, (156)
"Great location. Very nice property. Made the weekend stay a success "
The price is AU$402
includes taxes & fees
21 July - 22 July
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Stonington borough 2 bedroom, Sleeps 6 guests, close to beach,

10.0 out of 10, Exceptional, (64)
"Great spot and beautiful home!"
The price is AU$1,392
includes taxes & fees
27 July - 28 July
Stonington borough 2 bedroom, Sleeps 6 guests, close to beach,

Coastal Antique farmhouse

10.0 out of 10, Exceptional, (5)
"simply beautiful, the yard, the kitchen, the bathroom in every bed-room. The house is just full of charm. We rented it for our family traveling from Boston to attend my son's wedding, and we couldn't have been happier! Would love to find a reason to return"
The price is AU$1,813
includes taxes & fees
6 Aug - 7 Aug
Coastal Antique farmhouse

Gambler's Getaway

7.2 out of 10, Good, (5)
"Very clean and great beds."
The price is AU$621
includes taxes & fees
21 July - 22 July
Gambler's Getaway

Mystic Coastal Gem: 3BR Ideal for Families!

10.0 out of 10, Exceptional, (33)
"It was a wonderful stay! Perfect location, amenities and fun!"
The price is AU$995
includes taxes & fees
28 July - 29 July
Mystic Coastal Gem: 3BR Ideal for Families!

The Blue Anchor House · walk Mystic-Train/Aquarium

10.0 out of 10, Exceptional, (3)
"This was an adorable house with great access to downtown Mystic. The house is well updated and very clean. We would stay here again for sure. It was a very comfortable experience. "
The price is AU$942
includes taxes & fees
27 July - 28 July
The Blue Anchor House · walk Mystic-Train/Aquarium

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (145)
"Had a nice time. The house was well furnished. "
The price is AU$896
includes taxes & fees
17 Aug - 18 Aug
Charming Historic House in Downtown Mystic

Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.

10.0 out of 10, Exceptional, (49)
"Amazing home away from home. Very clean and walkable. It was a perfect girls trip weekend "
The price is AU$1,140
includes taxes & fees
28 July - 29 July
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.

Maritime History Meets Modern Comfort at the Carriage House in Old Mystic, CT!

10.0 out of 10, Exceptional, (4)
"We had a perfect stay in Mystic at the carriage house. It was such a fun and unique property!"
The price is AU$1,742
includes taxes & fees
29 July - 30 July
Maritime History Meets Modern Comfort at the Carriage House in Old Mystic, CT!

A Mystic Stay as Sweet as Apple Pie!

2.0 star property
The price is AU$350
includes taxes & fees
30 July - 31 July
A Mystic Stay as Sweet as Apple Pie!

Welcome to Williams Home & Smith Cottage- A Nautical New England Inspiration!

10.0 out of 10, Exceptional, (5)
"We stayed here because my daughter was getting married in Mystic. Words really can’t describe this place. I absolutely loved everything about it and we will most definitely be back!! Debbie and Paul are great hosts!"
The price is AU$2,108
includes taxes & fees
14 Aug - 15 Aug
Welcome to Williams Home & Smith Cottage- A Nautical New England Inspiration!

Historic 1807 Williams Home... A Nautical New England Inspiration!

10.0 out of 10, Exceptional, (9)
"Everything was wonderful! Host was so kind and helpful! Great house and the location was close to everything! Couldn't have been better! Hope to visit again! "
The price is AU$1,247
includes taxes & fees
30 July - 31 July
Historic 1807 Williams Home... A Nautical New England Inspiration!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Old Saybrook Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Old Saybrook?

Yes, there are holiday rentals in Old Saybrook close to Saybrook Country Barn, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the popular beaches and shops in Old Saybrook. Allow some time to check out the spas during your trip.

What are some of the best holiday rentals that Old Saybrook has to offer?

Adorable ranch in beach community: This highly rated holiday home rental in Old Saybrook is located near the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Old Saybrook?

Choose from 57 Expedia holiday rentals in Old Saybrook for a memorable holiday.

What’s there to see and do in Old Saybrook?

Family-friendly attractions include Saybrook Country Barn and Stay and Play LLC, whereas Harvey's Beach and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Katharine Hepburn Cultural Arts Center and Essex Saybrook Antique Village Shopping Center.

What’s a holiday rental in Old Saybrook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Saybrook. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.