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Compare 921 Vacation Homes in Old Saybrook with updated reviews, rates, and availability.

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 SAR 566
SAR 1,218 total
includes taxes & fees
13 Mar - 14 Mar
Charming Historic House in Downtown Mystic

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (23)
"This was the BEST decision for our family. The house was very cozy, old charm feel with some modern updates. The downstairs bathroom had a Spa vibe. We loved the 6 bedrooms & spacious kitchen & dining room. Loved how close it was to food & entertainment. The walk to the beach was only 10 minutes & very safe. We are use to blinds and/or shades, so just having light curtains for the windows was"
Large Charming Historic House close to Beaches

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (80)
"Walks on the beach are wonderful during low tide. Our dog absolutely loved it. During high tide the water does come up to the stairs leading to the beach,which is kind of cool. The bed was comfortable. There was a bad storm during our stay which created some undesirable conditions. Mother nature can not be controlled. Jon and Carolyn were accommodating and kind by offering us partial compensation for something that was not their fault. Overall, with some minor inconveniences we enjoyed our stay...
Waterfront House with picture-perfect views from all 3 levels.

Romantic Guesthouse in Historic Downtown Waterfront District!

10.0 out of 10, Exceptional, (169)
"What a lovely stay! Location is convenient to down town. Large bathroom, clean and comfy sitting/TV area, everything you need to cook and a comfy bedroom! We loves our stay and cant wait to come again! "
Romantic Guesthouse in Historic Downtown Waterfront District!

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

10.0 out of 10, Exceptional, (35)
"House was absolutely perfect for our needs. Great area, lots to do. Definitely would go back and recommend to others "
The price is SAR 731
SAR 1,841 total
includes taxes & fees
31 Mar - 1 Apr
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"The house easily accommodated my friends and family for a weekend of relaxation. The place is very spacious with all modern amenities. We especially loved waking up to the gorgeous view of the lake in the back. The views were breathtaking. Would definitely consider going back. "
The price is SAR 1,257
SAR 3,317 total
includes taxes & fees
13 Mar - 14 Mar
Luxe Lake House in Connecticut

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (88)
"Everything was just fine - nothing spectacular but good enough for a short stay. Extremely safe feeling location"
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Charming, Historic, 4BR 3BA Seaside Mystic Getaway, Walk To Seaport

10.0 out of 10, Exceptional, (130)
"My family and friends stayed for two nights. The house was super clean, well appointed, close to the main strip, and communicating with the property manager was super easy. The street was quiet and being able to have your doggo with you made this spot pretty perfect. Would love to visit again!"
Charming, Historic, 4BR 3BA Seaside Mystic Getaway, Walk To Seaport

3-bedroom vacation home just a 5-min walk to Main Street, Mystic

10.0 out of 10, Exceptional, (58)
"Great location, clean and perfectly suited to our group with 3 bedrooms and baths for each. Visited for an event at USCGA which is a short drive away and comfortably hosted friends from school and our family from west coast. The younger generation could walk to fun places close by while we stayed in and enjoyed the cozy fire in living room. Great breakfast at popover. Hosts were communicative and super and everything was great! "
3-bedroom vacation home just a 5-min walk to Main Street, Mystic

A Family Heirloom - Historic 1839 Downtown Mystic Home

10.0 out of 10, Exceptional, (88)
"This historic home checks all the boxes: convenient location; comfortable furniture and bed; well thought-out decor that is stylish and enhances the home; efficient kitchen; parking; strong water pressure in the shower; homey vibe; full size washer & dryer; quiet neighborhood; did I say the location couldn't be better? Thank you, Lynsey!!!"
A Family Heirloom - Historic 1839 Downtown Mystic Home

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (18)
"Very fun location near the beach. Beach is small but really a nice place to be. House worked well for our family of 4. Sun room was very nice."
Oceanfront Beach House lay in bed and hear the waves, boats , birds

Regency Inn & Suites

The price is SAR 285
SAR 467 total
includes taxes & fees
19 Mar - 20 Mar
Regency Inn & Suites

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

Historical New England coastal holiday home-2 min. from Ocean Beach

10.0 out of 10, Exceptional, (34)
"Everything was amazing! The house, the owners and time with friends. The house was wonderfully appointed, the beds were comfortable and the water was in sight from the front porch. Would DEFINITELY stay here again! "
Historical New England coastal holiday home-2 min. from Ocean Beach

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!

9.6 out of 10, Exceptional, (45)
"We stayed for the weekend to attend a wedding nearby and it was the perfect little cottage for a beach getaway! The place was very clean and so beautifully decorated, and the location can't be beat!"
The price is SAR 450
SAR 1,053 total
includes taxes & fees
10 Apr - 11 Apr
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Your Charming 4BR Retreat Home Minutes from Casino Excitement!

10.0 out of 10, Exceptional, (1)
"This was a great home for what we needed it for. Close to Foxwoods Casino which was our purpose for the stay. The home was comfortable and clean. No issues!"
The price is SAR 1,125
SAR 2,491 total
includes taxes & fees
26 Mar - 27 Mar
Your Charming 4BR Retreat Home Minutes from Casino Excitement!

Waterfront Lakehouse in Clinton, CT with Hot Tub!

7.0 out of 10, Good, (2)
"My family and I absolutely loved our stay at this home! It was the perfect retreat for us, and we thoroughly enjoyed the hot tub and the breathtaking sunset views, especially while cooking in the beautifully designed kitchen. The kitchen was fully equipped, making it easy to prepare an amazing family dinner. The town of Clinton was absolutely charming, with the friendliest people, and we fell in love with Hammonasset Beach—it’s a must-visit! We’ll definitely be returning in the summer. The...
Waterfront Lakehouse in Clinton, CT with Hot Tub!

Foxwoods and Mystic are both close by this private home with a Pool and Hot tub.

2.0 star property
10.0 out of 10, Exceptional, (8)
"We only stayed one night but the home was beautiful and very clean"
Foxwoods and Mystic are both close by this private home with a Pool and Hot tub.

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
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

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

9.8 out of 10, Exceptional, (127)
"We loved our stay!"
The price is SAR 1,129
SAR 2,293 total
includes taxes & fees
25 Mar - 26 Mar
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

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

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
The price is SAR 750
SAR 1,693 total
includes taxes & fees
5 Apr - 6 Apr
adorable ranch in beach community
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.