Search Vacation Homes in Old Saybrook

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Old Saybrook

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (133)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (5)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is AED 1,345
AED 2,962 total
includes taxes & fees
30 Jul - 31 Jul
Thames River Retreat · CT College+Casinos+USCGA

Charming 1845 Home in the Heart of Mystic – Walk to Everything!

9.8 out of 10, Exceptional, (149)
"Super time. Property is confidently located which made it easy to walk everywhere."
The price is AED 865
AED 1,589 total
includes taxes & fees
20 Jul - 21 Jul
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

6.0 out of 10, (4)
"Really convenient location breakfast was good. Rooms were clean."
The price is AED 308
AED 428 total
includes taxes & fees
20 Jul - 21 Jul
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

9.8 out of 10, Exceptional, (156)
"My husband and I had the best time for a long weekend at Dorothy's property. The very specific charm to the area was very apparent in this cottage! Even the bathroom was just adorable with the floral tile! It was very clean and the perfect size for us (could easily accommodate more than 2 with the pull out sofa). Minutes away from Stonington and Mystic, there is so much to do. We will definitely be back! I already miss hearing all the birds while sitting on the back porch swing."
The price is AED 459
AED 951 total
includes taxes & fees
20 Jul - 21 Jul
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Shoreline Oasis

8.0 out of 10, Very Good, (2)
"The house and town were adorable. The space was the second floor. It was clean and and comfortable. "
The price is AED 657
AED 968 total
includes taxes & fees
21 Jul - 22 Jul
Shoreline Oasis

Perfect Mid-Century Private Waterfront East Hampton Retreat!

10.0 out of 10, Exceptional, (79)
"Very nice and relaxing stay in Springs! "
Perfect Mid-Century Private Waterfront East Hampton Retreat!

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (145)
"Had a nice time. The house was well furnished. "
The price is AED 1,271
AED 2,119 total
includes taxes & fees
17 Aug - 18 Aug
Charming Historic House in Downtown Mystic

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (90)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Another rental season is coming up.

10.0 out of 10, Exceptional, (16)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.

Regency Inn and Suites - Non Smoking King

7.0 out of 10, Good, (2)
"Roadway and parking could use some repairs"
The price is AED 308
AED 428 total
includes taxes & fees
20 Jul - 21 Jul
Regency Inn and Suites - Non Smoking King

The Seaport Bridgeman - All things Mystic steps from your door

10.0 out of 10, Exceptional, (21)
"We had a great stay. Highly recommended!"
The Seaport Bridgeman - All things Mystic steps from your door

Perfect beach house getaway within walking distance to the beach

8.6 out of 10, Excellent, (7)
"Great weekend getaway - close to the beaches and towns. Lovely little house with firepit and very quiet neighborhood."
Perfect beach house getaway within walking distance to the beach

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Had a great stay with extended family. House had everything we needed plus a great view of a quiet lake. Was a nice quite place to have a relaxing fun filled weekend."
Grammy's Lake House w/ Private Waterfront Access

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

8.0 out of 10, Very Good, (1)
"Overall a great stay. The kids didn't want to leave and neither did we."
The price is AED 1,983
AED 3,316 total
includes taxes & fees
27 Jul - 28 Jul
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

Central to Mystic and Vineyards

9.8 out of 10, Exceptional, (22)
"The house was just perfect for our extended family. Comfortable beds, well supplied kitchen, clean, plenty of seating. We enjoyed the gas fireplace, proximity to town and the acquarium. Plenty of room for everyone."
Central to Mystic and Vineyards

Walk to Historic Downtown Mystic! <br>Best Location—beach, marinas, eateries!

9.2 out of 10, Wonderful, (13)
"Property was nice, within walking distance of the town center and had a nice area to relax when we were back at the place."
Walk to Historic Downtown Mystic! <br>Best Location—beach, marinas, eateries!

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

4.8 out of 10, (3)
"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (45)
"Home was very comfortable and a great location. The views were spectacular. Owner gave us great recommendations for restaurants and nearby attractions. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

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

10.0 out of 10, Exceptional, (157)
"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
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

Top Old Saybrook Hotel Reviews