Holiday Homes in Old Saybrook

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Featured Holiday Homes in Old Saybrook

Cozy 2 bedroom home located minutes from downtown
Interior

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (30)
"A very comfortable short stay in a convenient location"
Cozy 2 bedroom home located minutes from downtown
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
Private kitchen

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

10.0 out of 10, Exceptional, (2)
"Waterfront location by a marina was beautiful. The place is welcoming with a bright, cozy living area. Rooms were clean and spacious, bathrooms modern, kitchen, grill, and deck to enjoy. Had a great experience overall."
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Outdoor pool

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (103)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Modern Cape Downtown Mystic
Interior

Modern Cape Downtown Mystic

10.0 out of 10, Exceptional, (26)
"Delightful property convenient to the seaport as well as walk downtown Stan was an excellent host Very accommodating Would definitely stay again"
Modern Cape Downtown Mystic
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals."
The price is AU$787
includes taxes & fees
8 Oct - 9 Oct
McAngel Haven: 5 mins from Yale
Sweet Mystic Retreat
Fridge, microwave, oven, stovetop

Sweet Mystic Retreat

10.0 out of 10, Exceptional, (250)
"The house was very clean, plenty of space and well stocked. Would definitely stay there again"
Sweet Mystic Retreat
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Beach nearby

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.4 out of 10, Exceptional, (14)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
5 Minute Walk to Downtown Mystic
Property grounds

5 Minute Walk to Downtown Mystic

9.6 out of 10, Exceptional, (96)
"Excellent communication with property manager, great location to walk into Mystic shops"
5 Minute Walk to Downtown Mystic
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!

9.8 out of 10, Exceptional, (7)
The price is AU$1,028
includes taxes & fees
23 Oct - 24 Oct
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
New Madison beach house - Ocean front- Great views- booking Summer 2025
Exterior

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (67)
"The house is perfectly located. Quiet area but close to downtown Madison and Guilford and so much the CT shoreline has to offer. "
New Madison beach house - Ocean front- Great views- booking Summer 2025
The SandPiper
Terrace/patio

The SandPiper

9.8 out of 10, Exceptional, (25)
"My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone."
The SandPiper
Ranch style living at its best with country garden & patio!
Exterior

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (14)
"the host was really great about getting back to us when we had a question or problem . his home was comfortable and artistic. the location was also easy to get to and the neighborhood was quiet and comvenient to all your needs."
Ranch style living at its best with country garden & patio!
Sea Breeze Paradise: Beachfront & Panoramic Views
TV, fireplace, offices

Sea Breeze Paradise: Beachfront & Panoramic Views

9.8 out of 10, Exceptional, (6)
"Everything was perfect, very comfortable and the location was outstanding."
Sea Breeze Paradise: Beachfront & Panoramic Views
I’ve had the best guests!
Outdoor pool

I’ve had the best guests!

10.0 out of 10, Exceptional, (26)
"House was beautiful - clean -perfect to hang in - pool was great, very private and relaxing - host was hospitable, friendly and accommodating - can’t wait yo go back in the fall!"
I’ve had the best guests!
Charming Historic House in Downtown Mystic
Smart TV, video games, books, stereo

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (155)
"Such a unique home in the lovely town! Much to see and do. We need a longer stay. Thank you. "
The price is AU$610
includes taxes & fees
5 Oct - 6 Oct
Charming Historic House in Downtown Mystic
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Property grounds

Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

8.2 out of 10, Very good, (10)
"Affordable, fun, relaxing house. Indoor and outdoor things to do. Some pretty glass decor in the dining room, so I easily moved a few things to temporarily kid proof it. A/C in bedrooms, ceiling fans in almost every room. The hosts were very responsive and addressed our concerns exceptionally well."
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Dining

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (68)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Cape Cod home in great location! Walk to downtown
Beach

Cape Cod home in great location! Walk to downtown

9.4 out of 10, Exceptional, (156)
"Great place to stay in a nice location.Enjoyed our vacation here."
Cape Cod home in great location! Walk to downtown
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Exterior

Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.

10.0 out of 10, Exceptional, (50)
"The house is adorable and so nicely appointed. It was a perfect location for a quick walk to downtown or to the Museum. Chris is a fabulous host and so accommodating. We would definitely stay again!"
The price is AU$970
includes taxes & fees
6 Oct - 7 Oct
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
On the beach, sun-loungers, beach towels

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (127)
"Fantastic all around!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
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

Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

10/10 Excellent
"The room is a little dated but suitable"
Hugh 3-night trip
Posted 1 day ago
Holiday Inn Norwich by IHG

Find out more about Old Saybrook

Find out more about Old Saybrook

Old Saybrook Holiday Homes information

Number of reviews
1,134
Accommodation
1126 Holiday Homes
Lowest Price
AU$610
Highest Price
AU$1,028