Search Vacation Homes in Old Saybrook

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Vacation Homes in Old Saybrook

"The host was nice, helpful and easy to communicate with. Our room had an assigned bathroom, it wasn’t in the room, but just down the hall. That worked fine for us. We needed a clean, reasonably priced place for an overnight stay on our road trip and this ticked all the boxes."

￥18,061 total

includes taxes & fees

Oct 5 - Oct 6

"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"

￥38,725 total

includes taxes & fees

Oct 5 - Oct 6

"The home was very clean and welcoming."

￥61,636 total

includes taxes & fees

Oct 5 - Oct 6

"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. "

￥80,476 total

includes taxes & fees

Oct 5 - Oct 6

"We loved our stay!"

￥74,399 total

includes taxes & fees

Oct 6 - Oct 7

￥947,440 total

includes taxes & fees

Oct 8 - Oct 9

"Excellent stay! Where else could you accommodate 8 people with 4 king size beds and all the kitchen and housekeeping supplies you need. Well thought out and very comfortable outside and interior areas to relax in.Just a great experience"

￥97,740 total

includes taxes & fees

Oct 20 - Oct 21

"Loved the personal touches!"

￥30,633 total

includes taxes & fees

Nov 2 - Nov 3

1 bedroom, iron/ironing board, WiFi, bed sheets

"Excellent option for a short stay near the heart of it all in Wallingford."

￥41,308 total

includes taxes & fees

Oct 8 - Oct 9

"I was very pleased with the accomodations. I had everything I needed and it was comfortable and quiet. I was able to get my research done and enjoyed the peaceful setting, and it was convenient to the friends and family I visited during my stay. I will definitely stay here again. "

￥42,803 total

includes taxes & fees

Oct 5 - Oct 6

"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"

￥59,598 total

includes taxes & fees

Oct 7 - Oct 8

"Great stay, charming cottage, hope to return"

￥39,013 total

includes taxes & fees

Oct 6 - Oct 7

"This was a great find so close to home when my family needed a place to stay for a week. The house was clean, inviting and the communication with the property manager was amazing! Very fast to respond!"

￥57,414 total

includes taxes & fees

Oct 29 - Oct 30

"We stayed with this host for a weekend wedding in RI--easy check in and check out, great location. Thanks so much! (:"

￥40,802 total

includes taxes & fees

Oct 6 - Oct 7

2 bedrooms, iron/ironing board, free WiFi, bed sheets

"We visited here for a weekend in the Mystic area. Our daughter joined us for an evening and the home was cozy and comfortable for 3 adults. The check in process was seamless and communication with the host was always timely. They thought of everything to make our stay enjoyable and everything was within arms reach. The home is located in a great spot and enabled us to enjoy many surrounding areas. Pawcatuck/Westerly, Mystic, Watch Hill... all were very close so this was a perfect base of...

￥52,241 total

includes taxes & fees

Oct 28 - Oct 29

"Adam was super responsive to all questions and the small cottage on the water was the perfect location for a quick getaway! We will be back!"

￥41,157 total

includes taxes & fees

Oct 28 - Oct 29

"Beautiful seaside cottage. Updated and well appointed, bidet, fire pit and more. Very close to several beaches. Driving distance to many attractions, statue of liberty, and more. I would stay again. "

￥24,148 total

includes taxes & fees

Oct 29 - Oct 30

"loved it so much, beautiful property 100 % would stay again "

￥75,659 total

includes taxes & fees

Oct 15 - Oct 16

"We stayed here on our last night of a month long vacation. After a month of travel, you want convenience and comfort. This place offered us a fantastic last night away from home. It’s right across the street from the train station, easy walking to shops and dining, and just an overall beautiful apartment. It was clean and cozy with immaculate decorating. The entry and exit were easy. Accommodations were superior. Don’t forget to grab pizza!! "

￥55,905 total

includes taxes & fees

Oct 8 - Oct 9

￥22,410 total

includes taxes & fees

Oct 31 - Nov 1

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Old Saybrook Hotel Reviews

Clarion Inn

10/10 Excellent

"Courteous and helpful staff at checkin. Near Several restaurant options including Outback Steakhouse. A wonderful pet-friendly hotel"

New Haven Hotel

10/10 Excellent

"Let me start off by saying that I first came during Christmas and New Years of 2024 and it was solely because of my experience with interacting with Diahema or Dlahema. The lady at the front desk was super sweet, friendly and very inviting. Being introduced to the hotel from her made me want to come back a second time. While there was a $200 difference from the 1st visit to the 2nd, it still like it was worth. There was a small issue I had with a questionable bedspread on my bed that got corrected immediately. For the price of the room, I would think that a stained bedspread would be the last thing I'd think to have to complain about but again, swift response and still pleasant interactions. I would definitely stay at this hotel again."

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent

"Room service was great made sure we had everything we needed daily. Front desk very helpful. Was quiet until last night party on 2nd floor people running up and down hallway child kicked our door very hard around 2am. I believe mother worked for hotel and had family party out of control my husband got up and went out they quieted down after that.Overall the place was great though."

Find out more about Old Saybrook

Old Saybrook Vacation Homes information

Number of reviews	268
Accommodation	1024 Vacation Homes
Lowest Price	￥18,061
Highest Price	￥947,440

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Unlock instant savings with Member Prices

Search Vacation Homes in Old Saybrook

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Homes in Old Saybrook

Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi

Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi

Shoreline Oasis

Shoreline Oasis

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

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

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.

Unique Retreat w/ Private Patio, 4 King Beds & BBQ

Unique Retreat w/ Private Patio, 4 King Beds & BBQ

A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment

Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!

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

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

Coastal Retreat • 2BR Near Beaches & Mystic

Coastal Retreat • 2BR Near Beaches & Mystic

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA

Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale

The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

Pleasant apartment with AC in charming New Haven

Pleasant apartment with AC in charming New Haven

Top Old Saybrook Hotel Reviews

Clarion Inn

Find out more about Old Saybrook

Find out more about Old Saybrook

Old Saybrook Vacation Homes information

Explore a world of travel with Expedia

Explore a world of travel with Expedia

More Accommodation Types in Old Saybrook

All Accommodation Types

Be inspired: Top Vacation Homes destinations in 2025