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

Old Saybrook Vacation Rentals

  • 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
4 Sep - 6 Sep
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 vacation rentals

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

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 SAR 422
SAR 834 total
includes taxes & fees
15 Sep - 16 Sep
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

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 SAR 599
SAR 1,191 total
includes taxes & fees
15 Sep - 16 Sep
Cozy Lakefront Tiny House
Beach nearby

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 SAR 663
SAR 1,486 total
includes taxes & fees
14 Sep - 15 Sep
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
1 bedroom, WiFi (free), bed sheets

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 SAR 545
SAR 1,122 total
includes taxes & fees
15 Sep - 16 Sep
Lakefront Boho Tiny House
Private kitchen

5. 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 SAR 826
SAR 1,750 total
includes taxes & fees
9 Sep - 10 Sep
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Sun loungers, beach towels

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 SAR 591
SAR 1,374 total
includes taxes & fees
3 Sep - 4 Sep
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
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 SAR 1,445
SAR 2,595 total
includes taxes & fees
31 Aug - 1 Sep
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Dining

8. Summer is filling up-Beach, Shopping and Golf

Summer is filling up-Beach, Shopping and Golf
Clinton
10.0 out of 10, Exceptional, (5 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 SAR 957
SAR 2,646 total
includes taxes & fees
18 Aug - 19 Aug
Summer is filling up-Beach, Shopping and Golf
Exterior

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 SAR 1,973
SAR 3,277 total
includes taxes & fees
18 Aug - 19 Aug
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Beach

10. 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 SAR 1,194
SAR 2,781 total
includes taxes & fees
15 Sep - 16 Sep
Beachside Bliss w/ Game Room, Gym & Golf Green
Coffee/tea maker, microwave, oven, stovetop

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 SAR 1,051
SAR 2,039 total
includes taxes & fees
15 Sep - 16 Sep
Entire Vacation Home in Waterford Connecticut
Dining

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 SAR 2,008
SAR 3,444 total
includes taxes & fees
20 Aug - 21 Aug
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Property grounds

13. 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, (7 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 SAR 1,220
SAR 1,580 total
includes taxes & fees
19 Aug - 20 Aug
NEW Coastal Cottage 2 Miles to Beach + Lake Access
Outdoor dining

14. 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 SAR 1,400
SAR 2,422 total
includes taxes & fees
30 Aug - 31 Aug
Direct Lakefront - Stunning Views and Panoramic Sunsets
Dining

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, (40 reviews)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Beach nearby

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 SAR 939
SAR 2,009 total
includes taxes & fees
15 Sep - 16 Sep
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
View from property

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, (180 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 SAR 507
SAR 929 total
includes taxes & fees
24 Aug - 25 Aug
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Flat-screen TV

18. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is SAR 1,193
SAR 1,363 total
includes taxes & fees
17 Sep - 18 Sep
North Fork Resort
Beach nearby

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 SAR 514
SAR 1,147 total
includes taxes & fees
15 Sep - 16 Sep
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Condo | Terrace/patio

20. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (284 reviews)
"Great place!"
United States
Christine
The price is SAR 1,151
SAR 1,649 total
includes taxes & fees
7 Sep - 8 Sep
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.
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

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

8/10 Good
"Mediocre at best. Very very basic rooms. I came here in the early 2000s and I don't think it's been renovated since. Staff was helpful"
Jenn 3-night trip
Posted 3 hours ago
Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

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 45 Expedia vacation rentals in Old Saybrook for a memorable vacation.

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

Family-friendly attractions include Stay and Play LLC and Saybrook Country Barn, 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 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.