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Check prices for these dates

Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul
In one month
1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Browse Select Old Saybrook Holiday Homes

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Beach nearby, sun-loungers, beach towels

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 £399
includes taxes & fees
6 Jul - 7 Jul
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Entire Vacation Home in Waterford Connecticut
Microwave, oven, stovetop, dishwasher

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 £409
includes taxes & fees
20 Jul - 21 Jul
Entire Vacation Home in Waterford Connecticut
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Private kitchen

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

The price is £313
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
Dishwasher

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 £521
includes taxes & fees
9 Jul - 10 Jul
The Beach Nest-Lux Cottage Steps to the Beach
Shoreline Oasis
Exterior

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 £195
includes taxes & fees
15 Jul - 16 Jul
Shoreline Oasis
Beach front property steps from Long Island Sound!
Interior

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 £1,000
includes taxes & fees
18 Jul - 19 Jul
Beach front property steps from Long Island Sound!
2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS
Property grounds

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!"
2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS
adorable ranch in beach community
Beach nearby

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 £473
includes taxes & fees
15 Jul - 16 Jul
adorable ranch in beach community
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕
Interior

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

9.6 out of 10, Exceptional, (130)
"We loved our stay!"
The price is £708
includes taxes & fees
8 Jul - 9 Jul
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
Smart TV, fireplace

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

The price is £728
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
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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
Fridge, microwave, oven, stovetop

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 £192
includes taxes & fees
14 Jul - 15 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,
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (63)
"Great spot and beautiful home!"
Stonington borough 2 bedroom, Sleeps 6 guests, close to beach,
Coastal Antique farmhouse
Fridge, microwave, oven, stovetop

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 £887
includes taxes & fees
30 Jul - 31 Jul
Coastal Antique farmhouse
Gambler's Getaway
Private kitchen

Gambler's Getaway

7.2 out of 10, Good, (5)
"Very clean and great beds."
The price is £298
includes taxes & fees
30 Jul - 31 Jul
Gambler's Getaway
Mystic Coastal Gem: 3BR Ideal for Families!
Outdoor dining

Mystic Coastal Gem: 3BR Ideal for Families!

10.0 out of 10, Exceptional, (33)
"It was a wonderful stay! Perfect location, amenities and fun!"
Mystic Coastal Gem: 3BR Ideal for Families!
The Blue Anchor House · walk Mystic-Train/Aquarium
Terrace/patio

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 £283
includes taxes & fees
3 Jul - 4 Jul
The Blue Anchor House · walk Mystic-Train/Aquarium
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Fridge, microwave, oven, stovetop

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 £584
includes taxes & fees
7 Jul - 8 Jul
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Charming Historic House in Downtown Mystic
Smart TV, video games, books, stereo

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.
Property grounds

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

10.0 out of 10, Exceptional, (48)
"Amazing home away from home. Very clean and walkable. It was a perfect girls trip weekend "
The price is £541
includes taxes & fees
14 Jul - 15 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.
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