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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 857 Vacation Homes in Old Saybrook with updated reviews, rates, and availability.

Groton Home < 1 Mi to Beach on Long Island Sound!
Groton Vacation Rental | 4BR | 3.5BA | 3,580 Sq Ft | 3 Steps to Enter

Groton Home < 1 Mi to Beach on Long Island Sound!

10.0 out of 10, Exceptional, (3)
"Beautiful place with fabulous views. We rented for a family funeral. Had more than enough space to host a get together for family (about 25 people). Hosts were flexible about giving us an extra hour to get packed up. "
Groton Home < 1 Mi to Beach on Long Island Sound!
Enjoy Autumn with us.
Exterior

Enjoy Autumn with us.

10.0 out of 10, Exceptional, (13)
"Ladies weekend. The home was clean and comfortable. We loved how all the kitchen cabinets and drawers were labeled. The host was responsive and accessible The neighborhood was beautiful and close to several of the wineries "
Enjoy Autumn with us.
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
Main Living Area

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

8.6 out of 10, Excellent, (26)
"I recently had the pleasure of spending time at a vacation house in Stonington, Connecticut, and I cannot express enough how fantastic our stay was. This property exceeded all of our expectations and provided our family with a truly memorable experience.From the moment we arrived, we were captivated by the stunning water views. The house is perfectly situated to showcase the beauty of the surrounding landscape, and we found ourselves mesmerized by the sunsets over the water each evening. It was...
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
Sweet Mystic Retreat
Exterior

Sweet Mystic Retreat

10.0 out of 10, Exceptional, (239)
"The hosts were extremely helpful and responsive to all my questions and requests.My family enjoyed our holiday vacation in the house. The location of the house was great.My only complaint is that there was a lot of black (cat?) hair in the living area. We had small crawling children and the hair was a concern."
Sweet Mystic Retreat
Brand new home minutes to casino
Kitchen

Brand new home minutes to casino

10.0 out of 10, Exceptional, (16)
"This was the perfect location and the home is as clean as they come and perfectly appointed. "
The price is AED 639
AED 1,355 total
includes taxes & fees
18 Feb - 19 Feb
Brand new home minutes to casino
Historic home in downtown Mystic-1 block from green, river, shops & restaurants
Street View (front of house)

Historic home in downtown Mystic-1 block from green, river, shops & restaurants

10.0 out of 10, Exceptional, (106)
"We had a great time staying at the Charles Mallory house. Our whole family of 10 from 3-70 really enjoyed everything the house and area had to offer. The owners were above excellent and ready with lots of local information, history, and info about their beautifully restored and loved home. "
Historic home in downtown Mystic-1 block from green, river, shops & restaurants
Eagles Nest at Mystic Manor
Exterior

Eagles Nest at Mystic Manor

10.0 out of 10, Exceptional, (102)
"We had a fantastic experience at the Eagles Nest ! The focus of our stay was golf & 35+ years of friendship and the Eagles Nest set up perfectly for our group of 7. First of all the home and property were immaculate upon arrival, nothing out of place, everything clean & glowing, and not a crumb to be found. The ample space allowed us to easily gather in open kitchen & Living Room areas and everyone had their own bedroom. Kitchen is loaded up with anything you could need / use to do any meal. We...
Eagles Nest at Mystic Manor
Cozy Westbrook Vacation Rental - Walk to Beach!
Westbrook Vacation Rental | 3BR | 1.5BA | 1 Step to Enter | 1,350 Sq Ft

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!
Rest, Relax, Retreat - A 3bdrm Mystic Getaway- Children 6+ welcome
Exterior

Rest, Relax, Retreat - A 3bdrm Mystic Getaway- Children 6+ welcome

10.0 out of 10, Exceptional, (155)
"We really enjoyed our stay at the cottage and already are planning to return. The cottage was well equipped with kitchen, bathroom and actual cable tv - super important as we traveled over prime football season. We were very comfortable, the area was quiet and very conveniently located near the holiday lights and the waterfront. "
Rest, Relax, Retreat - A 3bdrm Mystic Getaway- Children 6+ welcome
McAngel Haven: 5 mins from Yale
Spaciously Stylish Living Area with Fireplace and Dining View

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (10)
"Excellent to had a nice house like that "
The price is AED 937
AED 2,082 total
includes taxes & fees
17 Feb - 18 Feb
McAngel Haven: 5 mins from Yale
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Living room with big sectional

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

10.0 out of 10, Exceptional, (23)
"I wanted to surprise my husband with a weekend get-away for him and five of his buds. The house perfectly fit those needs. Plenty of beds and space. Room for them to break out the Board Games hang and Mary was a wonderful partner in answering my questions and dealing with the "surprise" aspect of the weekend. It also turns out that the location was perfect with plenty of town for them to see if they felt like getting out of the house. 2 hours from NJ and Boston made it a nice mid-point for my...
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Charming Historic House in Downtown Mystic
Exterior

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (129)
"This was a 10 out of 10 stay for us. The home was immaculate, stocked with everything you could need to feel at home. Very comfy beds and linens. Fantastic location and great hosts. Would definitely stay at this home again."
The price is AED 503
AED 1,122 total
includes taxes & fees
17 Feb - 18 Feb
Charming Historic House in Downtown Mystic
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Pool

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.
Newly renovated interior and exterior

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

10.0 out of 10, Exceptional, (34)
"The property is super clean and cozy. Chris was a really good host and was available and responsive to any questions.. The location is excellent being within walking distance of downtown and the seaport museum. We really enjoyed our stay and hope to visit again.the seaport museum. "
The price is AED 716
AED 1,750 total
includes taxes & fees
17 Feb - 18 Feb
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.
Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+
Exterior

Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

10.0 out of 10, Exceptional, (10)
"This may very well be the nicest house we have ever stayed in! It was spacious, clean and well stocked. It was so nice not to have to bring our own linens! We were pleasantly surprised with a hot tub. Thank you for a great stay!"
Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+
Cape Cod home in great location! Walk to downtown
charming cape ... close to RI beaches & walking distance to downtown Westerly!

Cape Cod home in great location! Walk to downtown

9.4 out of 10, Exceptional, (142)
"The house was clean and had a cozy feel. Good location too, with a lot of restaurants/ neat stores nearby. I would definitely recommend this if you're looking to go on vacation to Connecticut."
Cape Cod home in great location! Walk to downtown
The Secret Mermaid in downtown Mystic! Beautiful & just remodeled!
Exterior

The Secret Mermaid in downtown Mystic! Beautiful & just remodeled!

10.0 out of 10, Exceptional, (22)
"We had a wonderful weekend stay at Mia and Jon’s beautiful home. It is better than the pics. Spotlessly clean. The location is just a couple minutes walk to main area in mystic with shops/restaurants. The hosts left us a lovely gift card to use at a local bakery. Such a nice touch! The beds are so comfortable. The fireplace was perfect on our rainy day. The area is beautiful wish we had more time to walk around and explore. I would love to return in summer months!!! Thanks again Mia...
The Secret Mermaid in downtown Mystic! Beautiful & just remodeled!
Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property
DT Mystic Renovated 3BR Mystic Cape house
Living area

DT Mystic Renovated 3BR Mystic Cape house

10.0 out of 10, Exceptional, (39)
"Smooth communication and great location "
DT Mystic Renovated 3BR Mystic Cape house
Spectacular home with an amazing river view
Spectacular sunsets

Spectacular home with an amazing river view

9.6 out of 10, Exceptional, (73)
"The house is absolutely beautiful! The deck overlooking the river took everyone’s breath away. It was a perfect stay. Lots of room in the house. Clean and cozy. 15 minutes from Mohegan Sun. There’s not a lot of condiments to cook/eat with which is totally fine, really just a heads up to bring your own pepper, ketchup, etc. We would 10/10 recommend this place. "
Spectacular home with an amazing river view
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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Other property types in Old Saybrook

adorable ranch in beach community
Front of House

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
adorable ranch in beach community
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
Property grounds

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

9.4 out of 10, Exceptional, (33)
"Our second stay at the cottage. We spent a long weekend and the weather cooperated. The house is quite quirky, but has a really pleasant feel at home vibe. Beds were very comfortable. Kitchen could use some updates, but was sufficient. (still need a new can opener) The porch overlooking the Sound is magical. Nice neighborhood. If you have one...bring a golf cart! Lots of golf carts about. Host is always pleasant, communicating through Vrbo. We hope to return again. Thank you Khalig Family...
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Exterior

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (33)
"Lovely little cottage in a pretty, quiet neighborhood. Once you find it down the little lane, it's a great location to be in. Not far from town and close to the water, we really enjoyed relaxing at the house and in the backyard. Highly recommend."
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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.