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

Old Saybrook Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Old Saybrook holiday rentals

A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AU$313
includes taxes & fees
15 Sept - 16 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

2. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is AU$451
includes taxes & fees
16 Sept - 17 Sept
Cozy Lakefront Tiny House
A beach with waves, a clear sky, and a sandy shore.

3. 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 AU$528
includes taxes & fees
15 Sept - 16 Sept
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

4. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is AU$416
includes taxes & fees
15 Sept - 16 Sept
Lakefront Boho Tiny House
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

5. 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 AU$845
includes taxes & fees
21 Sept - 22 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A beach with a house in the background, a clear sky, and a calm sea.

6. 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
The price is AU$504
includes taxes & fees
24 Aug - 25 Aug
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A modern kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, and a granite countertop.

7. 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, (2 reviews)
"The home was very clean and welcoming."
United States
Michelle M.
The price is AU$634
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom house with WiFi, AC in lovely Waterford
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

8. 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 AU$1,000
includes taxes & fees
15 Sept - 16 Sept
Beachside Bliss w/ Game Room, Gym & Golf Green
An aerial view of a marina with boats docked, surrounded by residential buildings and greenery.

9. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (51 reviews)
"Great spot easy walk to the water and very close to town!"
United States
Genevieve G.
The price is AU$1,270
includes taxes & fees
24 Aug - 25 Aug
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
A glass-enclosed patio with a wooden table and wicker chairs, surrounded by glass doors and windows offering views of a wooded area.

10. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
The price is AU$1,085
includes taxes & fees
9 Sept - 10 Sept
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
A modern kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, and a granite countertop.

11. Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
9.0 out of 10, Wonderful, (4 reviews)
"Such a nice quiet property in Waterford, short distance away from many local restaurants and shops and 20 minutes away from the casino. "
United States
Elise Marie K.
The price is AU$749
includes taxes & fees
2 Sept - 3 Sept
Entire Vacation Home in Waterford Connecticut
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

12. Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
The price is AU$1,236
includes taxes & fees
23 Aug - 24 Aug
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

13. Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
10.0 out of 10, Exceptional, (1 review)
"Very peaceful and quiet. Beautiful view of the lake. Would definitely book again."
United States
James C.
The price is AU$798
includes taxes & fees
3 Sept - 4 Sept
Direct Lakefront - Stunning Views and Panoramic Sunsets
A stone fire pit with two Adirondack chairs, a wooden fence, and a black building with a red door.

14. NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here. The house has a cozy, homey feel and was a nice place to come back to after being out for the day. It was quiet, comfortable, and had a relaxed vibe that made the trip easy.The location was a big plus for us. Hammonasset Beach was only a few minutes away, and Madison center was just as close, which made it easy to grab dinner or pop out for anything we needed. The outdoor fireplace was also a really nice touch and made the evenings feel special.Overall, it was a...
United States
Moe B.
The price is AU$646
includes taxes & fees
27 Aug - 28 Aug
NEW Coastal Cottage 2 Miles to Beach + Lake Access
A spacious room with a large dining table and chairs, a sofa, and large windows offering a view of the sea and buildings.

15. 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, (41 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is AU$2,443
includes taxes & fees
6 Sept - 7 Sept
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
A beach with waves, a clear sky, and a sandy shore.

16. 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 AU$707
includes taxes & fees
15 Sept - 16 Sept
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
A cabin with a large window, surrounded by trees.

17. 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, (181 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is AU$347
includes taxes & fees
21 Sept - 22 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern house with a deck, outdoor seating, and a fire pit.

18. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is AU$504
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort
A stone pier leading to a beach with houses in the background.

19. 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 AU$406
includes taxes & fees
15 Sept - 16 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!

20. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (285 reviews)
"Great place!"
United States
Christine
The price is AU$617
includes taxes & fees
7 Sept - 8 Sept
Cliffside Resort Condominiums
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

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

8/10 Good
"Close to the casino, easy to get into, free parking, easy check-in. Free shuttle to casino was convenient on ride there, waiting with a bunch of concert goers for the ride back was a little much, but overall not bad."
Eric 1-night trip
Posted 3 hours ago
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Find out more about Old Saybrook

Everything you need to know about Old Saybrook holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Old Saybrook holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Saybrook holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Old Saybrook holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Saybrook. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old Saybrook holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Old Saybrook holiday rentals we have selected for you start as low as AU$313 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Old Saybrook rentals

At Expedia, we put the best Old Saybrook holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Old Saybrook rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Saybrook holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Saybrook. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Old Saybrook?

Yes, there are holiday rentals in Old Saybrook close to Katharine Hepburn Cultural Arts Center, or you can select a more secluded 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 holiday rentals that Old Saybrook has to offer?

The Hampton Sack a cheerful relaxing beach cottage: This holiday home rental outside of Old Saybrook is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Old Saybrook?

Choose from 45 Expedia holiday rentals in Old Saybrook for a memorable holiday.

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

Family-friendly attractions include Saybrook Country Barn and Stay and Play LLC, whereas Harvey's Beach and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Katharine Hepburn Cultural Arts Center and General William Hart House.

What’s a holiday rental in Old Saybrook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Saybrook. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.