Search Holiday Rentals in Old Saybrook

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Old Saybrook

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

9.6 out of 10, Exceptional, (5)
"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. "
The price is £388
includes taxes & fees
2 Jul - 3 Jul
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 £410
includes taxes & fees
19 Jul - 20 Jul
Entire Vacation Home in Waterford Connecticut

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

The price is £314
includes taxes & fees
22 Jul - 23 Jul
Charming 2-bedroom house with WiFi, AC in lovely Waterford

The Beach Nest-Lux Cottage Steps to the Beach

9.8 out of 10, Exceptional, (6)
"Quick weekend stay as we needed to be in the area for a soccer tournament. The house was super clean and had everything we needed. Would definitely stay again. "
The price is £522
includes taxes & fees
9 Jul - 10 Jul
The Beach Nest-Lux Cottage Steps to the Beach

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is £196
includes taxes & fees
6 Jul - 7 Jul
Shoreline Oasis

Beach front property steps from Long Island Sound!

10.0 out of 10, Exceptional, (15)
"Everyone had a great time, including our puppy! The location is fabulous and we enjoyed all the amenities inside and outside!"
The price is £1,001
includes taxes & fees
18 Jul - 19 Jul
Beach front property steps from Long Island Sound!

2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

10.0 out of 10, Exceptional, (33)
"We stayed at this wonderful property for 3 nights and it had everything we were looking and more! Looking forward to our next visit!"
The price is £481
includes taxes & fees
20 Jul - 21 Jul
2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is £475
includes taxes & fees
7 Jul - 8 Jul
adorable ranch in beach community

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

9.6 out of 10, Exceptional, (130)
"We loved our stay!"
The price is £717
includes taxes & fees
1 Jul - 2 Jul
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

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

The price is £782
includes taxes & fees
27 Jul - 28 Jul
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 £289
includes taxes & fees
9 Jul - 10 Jul
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, (153)
"Clean comfortable vintage property. Convenient to Stonington Borough, Mystic and Westerly."
The price is £193
includes taxes & fees
3 Jul - 4 Jul
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, (63)
"Great spot and beautiful home!"
The price is £674
includes taxes & fees
1 Jul - 2 Jul
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 £911
includes taxes & fees
30 Jul - 31 Jul
Coastal Antique farmhouse

Gambler's Getaway

7.2 out of 10, Good, (5)
"Very clean and great beds."
The price is £298
includes taxes & fees
6 Jul - 7 Jul
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 £521
includes taxes & fees
2 Jul - 3 Jul
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 £358
includes taxes & fees
3 Jul - 4 Jul
The Blue Anchor House · walk Mystic-Train/Aquarium

The Mystic Harbor House · walk downtown Mystic · train · aquarium

10.0 out of 10, Exceptional, (3)
"Loved the area. Loved the house. Very clean "
The price is £479
includes taxes & fees
1 Jul - 2 Jul
The Mystic Harbor House · walk downtown Mystic · train · aquarium

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (143)
"Had a nice time. The house was well furnished. "
The price is £376
includes taxes & fees
9 Jul - 10 Jul
Charming Historic House in Downtown Mystic

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

10.0 out of 10, Exceptional, (47)
"A perfect place for peace and relaxation! The family dog loved it too! We took our morning and evening walks, loved the proximity to town, and enjoyed sitting on the patio at night! "
The price is £547
includes taxes & fees
1 Jul - 2 Jul
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.
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.
Save an average of 15% on thousands of hotels when you're signed in

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 56 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.