A rocky beach with large boulders and the ocean in the background.

Old Saybrook Vacation Rentals

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Our top choices for Old Saybrook vacation rentals

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

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (13 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is CA $339
CA $713 total
includes taxes & fees
Sep 28 - Sep 29
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

2. 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, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is CA $407
CA $801 total
includes taxes & fees
Sep 28 - Sep 29
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

3. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is CA $234
CA $671 total
includes taxes & fees
Sep 28 - Sep 29
Adorable Cottage, 5 min walk to water & town

4. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Great host and property"
United States
Kevin K.
The price is CA $293
CA $746 total
includes taxes & fees
Sep 28 - Sep 29
Adorable Cottage with Cottage porch, walk to water & town

5. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $169
CA $320 total
includes taxes & fees
Oct 26 - Oct 27
1-bedroom cottage with Grove Beach 🏖️ access.

6. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is CA $168
CA $435 total
includes taxes & fees
Sep 29 - Sep 30
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

7. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is CA $223
CA $422 total
includes taxes & fees
Oct 7 - Oct 8
The gardners Cottage 1 mile from long Island Sound - pet friendly

8. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is CA $226
CA $440 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Lakefront Tiny House

9. Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our stay. It was very peaceful and relaxing. The view of the lake from sunrise to sunset was truly breathtaking."
United States
Chuck T.
The price is CA $356
CA $694 total
includes taxes & fees
Sep 28 - Sep 29
Direct Lakefront - Stunning Views and Panoramic Sunsets

10. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (10 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is CA $191
CA $400 total
includes taxes & fees
Oct 20 - Oct 21
Lakefront Boho Tiny House

11. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is CA $403
CA $976 total
includes taxes & fees
Oct 27 - Oct 28
Beachside Bliss w/ Game Room, Gym & Golf Green

12. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (96 reviews)
"Unbeatable views and professional hosts."
United States
Russell A.
The price is CA $990
CA $1,600 total
includes taxes & fees
Sep 28 - Sep 29
Direct waterfront renovated cottage.

13. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is CA $206
CA $491 total
includes taxes & fees
Oct 6 - Oct 7
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

14. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Great spot Very clean"
United States
Dorothy W.
The price is CA $233
CA $602 total
includes taxes & fees
Sep 29 - Sep 30
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

15. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (193 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
The price is CA $179
CA $271 total
includes taxes & fees
Oct 1 - Oct 2
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

16. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (58 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $369
CA $421 total
includes taxes & fees
Oct 27 - Oct 28
North Fork Resort

17. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (294 reviews)
"Great place!"
United States
Christine
The price is CA $334
CA $538 total
includes taxes & fees
Oct 25 - Oct 26
Cliffside Resort Condominiums

18. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is CA $159
CA $382 total
includes taxes & fees
Sep 30 - Oct 1
Insta-worthy Couples Retreat: Perfect for romantic getaway!

19. Lakeside Bliss

Lakeside Bliss
East Lyme
9.6 out of 10, Exceptional, (31 reviews)
"Lovely house - excellently equipped and fun decor. The owner was gracious and flexible and the location is beautiful. "
United States
Brenda M.
The price is CA $508
CA $769 total
includes taxes & fees
Oct 4 - Oct 5
Lakeside Bliss

20. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is CA $148
CA $198 total
includes taxes & fees
Sep 29 - Sep 30
The Tiny Cottage & Mini Farm
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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Top Old Saybrook Hotel Reviews

Find out more about Old Saybrook

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Old Saybrook. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Old Saybrook?

Yes, there are vacation rentals in Old Saybrook close to Katharine Hepburn Cultural Arts Center, or you can go with a more remote option if you're looking for a relaxing stay. Visitors like the popular beaches and shops in Old Saybrook. Allow some time to check out the spas during your trip.

What are some of the best vacation home rentals in Old Saybrook?

Steps to the Beach, Cozy Year Round Cottage Pet Friendly: Visitors like this Old Saybrook vacation home rental. It is located near the beach and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Old Saybrook?

Choose from 47 Expedia vacation rentals in Old Saybrook for a memorable vacation.

What’s there to see and do in Old Saybrook?

Harvey's Beach and Connecticut River are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Saybrook Country Barn. Other places in town to visit include Katharine Hepburn Cultural Arts Center and Essex Saybrook Antique Village Shopping Center.

What’s a vacation rental in Old Saybrook like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Saybrook. Vacation rentals offer extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips.