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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Old Saybrook holiday rentals

1 bedroom, desk, iron/ironing board, travel cot

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$946
HK$1,816 total
includes taxes & fees
6 Oct - 7 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Interior

2. 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 HK$1,299
HK$3,573 total
includes taxes & fees
13 Sept - 14 Sept
Adorable Cottage, 5 min walk to water & town
1 bedroom, free WiFi, bed sheets

3. 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 HK$1,087
HK$2,253 total
includes taxes & fees
14 Sept - 15 Sept
Lakefront Boho Tiny House
Smart TV, fireplace, books, offices

4. 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 HK$1,961
HK$4,007 total
includes taxes & fees
14 Sept - 15 Sept
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Coffee/tea maker, fridge, microwave, oven

5. 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)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is HK$1,372
HK$2,506 total
includes taxes & fees
7 Oct - 8 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

6. 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 HK$1,285
HK$2,505 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Lakefront Tiny House
Interior

7. 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 HK$2,259
HK$4,389 total
includes taxes & fees
28 Sept - 29 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Dining

8. 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 HK$1,714
HK$4,230 total
includes taxes & fees
14 Sept - 15 Sept
Adorable Cottage with Cottage porch, walk to water & town
Beach

9. 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 HK$1,613
HK$4,641 total
includes taxes & fees
15 Sept - 16 Sept
Beachside Bliss w/ Game Room, Gym & Golf Green
Sun-loungers, beach towels

10. 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, (1 review)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is HK$1,235
HK$2,846 total
includes taxes & fees
20 Sept - 21 Sept
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Dining

11. 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 HK$2,313
HK$5,935 total
includes taxes & fees
28 Sept - 29 Sept
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Outdoor dining

12. 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 HK$2,579
HK$4,647 total
includes taxes & fees
21 Sept - 22 Sept
Direct Lakefront - Stunning Views and Panoramic Sunsets
TV, books

13. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
The price is HK$5,490
HK$8,464 total
includes taxes & fees
28 Sept - 29 Sept
Direct waterfront renovated cottage.
View from property

14. 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, (187 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is HK$1,060
HK$1,580 total
includes taxes & fees
17 Sept - 18 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Flat-screen TV

15. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (54 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is HK$2,520
HK$2,879 total
includes taxes & fees
23 Sept - 24 Sept
North Fork Resort
Beach nearby

16. 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 HK$980
HK$2,263 total
includes taxes & fees
29 Sept - 30 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Front of property

17. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
3.0 star property
Montville
10.0 out of 10, Exceptional, (3 reviews)
"The pool was amazing, the host was great, very accessible and the property was prisine. The views alone made us immediately want to come back. Very clean and well stocked. "
United States
agata
The price is HK$1,294
HK$2,977 total
includes taxes & fees
16 Sept - 17 Sept
Private Guest House w/ Deck + Spectacular Views!
Terrace/patio

18. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (291 reviews)
"Great place!"
United States
Christine
The price is HK$2,266
HK$3,288 total
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums
Exterior

19. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (42 reviews)
"Very convenient location with good parking"
United States
Anonymous traveller
The price is HK$1,231
HK$2,079 total
includes taxes & fees
13 Sept - 14 Sept
Walk To Goodspeed Opera House!
1 bedroom, WiFi, bed sheets

20. Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
New London
10.0 out of 10, Exceptional, (14 reviews)
"Parking was easy and the room was the right siz."
United States
Vicente B.
The price is HK$847
HK$1,131 total
includes taxes & fees
13 Sept - 14 Sept
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
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

Grand Pequot Tower at Foxwoods

Grand Pequot Tower at Foxwoods

10/10 Excellent
"Everything was great"
Lesley 1-night trip
Posted less than an hour ago
Grand Pequot Tower at Foxwoods

Find out more about Old Saybrook

Search for holiday rentals in Old Saybrook on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Saybrook using one of the methods below:

  • View our selection of featured holiday rentals in Old Saybrook
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  • Enter your travel dates to view the best deals on holiday rentals in Old Saybrook while they last

Look no further and take a look at our great range of rental properties in Old Saybrook!

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?

Steps to the Beach, Cozy Year Round Cottage Pet Friendly: This highly rated holiday home rental in Old Saybrook 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 games in this rental home to help you unwind.

How many holiday rentals will I find in Old Saybrook?

Choose from 46 Expedia holiday rentals in Old Saybrook for a memorable holiday.

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 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.