Search Vacation Homes in Old Saybrook

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Old Saybrook vacation homes

Microwave, oven, stovetop, dishwasher

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
8.8 out of 10, Excellent, (3 reviews)
"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. "
United States
Jennifer A.
The price is AED 698
AED 1,567 total
includes taxes & fees
1 May - 2 May
Entire Vacation Home in Waterford Connecticut
Private kitchen

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

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is AED 551
AED 1,354 total
includes taxes & fees
1 May - 2 May
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is AED 1,286
AED 2,373 total
includes taxes & fees
6 May - 7 May
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AED 756
AED 2,163 total
includes taxes & fees
4 May - 5 May
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is AED 1,469
AED 2,850 total
includes taxes & fees
27 May - 28 May
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Property grounds

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
8.0 out of 10, Very Good, (2 reviews)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is AED 441
AED 1,032 total
includes taxes & fees
8 May - 9 May
Stylish Modern Stay Steps from the Ocean
Dining

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (36 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is AED 1,084
AED 2,337 total
includes taxes & fees
1 May - 2 May
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
TV

Victorian 4BR/2BA Modern Home

Victorian 4BR/2BA Modern Home
Laurel Hill
9.2 out of 10, Wonderful, (25 reviews)
"Great place and stay was really clean and comfy"
United States
Michael B.
The price is AED 504
AED 1,721 total
includes taxes & fees
3 May - 4 May
Victorian 4BR/2BA Modern Home
Smart TV, books

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

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Stonington
9.8 out of 10, Exceptional, (176 reviews)
"A bright and cozy vibe as well as being thoroughly equipped with everything to make our stay comfortable.We appreciated the winter escape and enjoyed Stonington, Mystic, and Westerly. A lovely stay!"
United States
Dawn R.
The price is AED 349
AED 919 total
includes taxes & fees
4 May - 5 May
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Terrace/patio

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (21 reviews)
"Only stayed for 1 night but the house was clean and had what our group needed. Beautiful location. "
United States
Alexander L.
The price is AED 1,160
AED 2,728 total
includes taxes & fees
4 May - 5 May
Thames River Retreat · CT College+Casinos+USCGA
Dining

Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA
Montville
10.0 out of 10, Exceptional, (2 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is AED 488
AED 1,269 total
includes taxes & fees
6 May - 7 May
Thames River Cottage · Near Casinos - USCGA
Smart TV

Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (51 reviews)
"It was cozy, clean and very close to Mohegan sun! "
United States
Lauren K.
The price is AED 493
AED 1,106 total
includes taxes & fees
1 May - 2 May
Cozy, comfy,quiet &close to casinos
Interior

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
9.8 out of 10, Exceptional, (10 reviews)
"Place is nice would stay again "
United States
nic
The price is AED 497
AED 1,512 total
includes taxes & fees
4 May - 5 May
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Smart TV, foosball

Peaceful Private Home by Two Casinos in the Woods

Peaceful Private Home by Two Casinos in the Woods
Preston
8.4 out of 10, Very Good, (7 reviews)
"We had a wonderful time here! The homeowners were very quick to answer any questions or concerns. The house was beautifully decorated and absolutely was perfect for our big group! "
United States
Shaina V.
The price is AED 697
AED 1,994 total
includes taxes & fees
5 May - 6 May
Peaceful Private Home by Two Casinos in the Woods
Dining

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is AED 843
AED 1,921 total
includes taxes & fees
3 May - 4 May
McAngel Haven: 5 mins from Yale
1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AED 433
AED 1,071 total
includes taxes & fees
1 May - 2 May
Once the old Schools house now a newly furnished Apartment
TV

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Montville
10.0 out of 10, Exceptional, (6 reviews)
"great place to stay"
United States
christopher
The price is AED 477
AED 1,188 total
includes taxes & fees
3 May - 4 May
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Terrace/patio

Tranquil Farmhouse Retreat

Tranquil Farmhouse Retreat
Montville
9.8 out of 10, Exceptional, (22 reviews)
"We had a great stay during the Thanksgiving holiday. We were able to enjoy the space of the house and the close proximity to Mohegan Sun."
United States
Allison R.
The price is AED 1,752
AED 3,445 total
includes taxes & fees
14 May - 15 May
Tranquil Farmhouse Retreat
Property grounds

Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only

Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only
West Mystic
10.0 out of 10, Exceptional, (3 reviews)
"We had a lovely experience in West Mystick at the Harbor House. The rental was lovely, clean, and contained enough of the necessary amenities. The view of the harbor was lovely. There were renters below us that had small children and at times that was very noisy. You could hear them running back and forth most of the evening. If they were playing music you could hear that as well. It was very cold during our time in Mystic so the heat was necessary. The baseboard heat was sufficient to keep...
United States
Suzanne S.
The price is AED 1,286
AED 1,662 total
includes taxes & fees
1 May - 2 May
Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only
2 bedrooms, desk, iron/ironing board, free WiFi

Private 2-bedroom in charming Norwich

Private 2-bedroom in charming Norwich
Norwich
8.4 out of 10, Very Good, (6 reviews)
"Our host was exceptionally responsive and very helpful. The home was very clean and comfortable. It was convenient to all of the local attractions. Private parking was an added bonus. "
United States
Kayla S.
The price is AED 231
AED 487 total
includes taxes & fees
4 May - 5 May
Private 2-bedroom in charming Norwich
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Saybrook Hotel Reviews

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Very clean and comfortable "
Carolyn 1-night trip
Posted 5 hours ago
New Haven Hotel

Explore a world of travel with Expedia