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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 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 AED 423
AED 828 total
includes taxes & fees
8 Sep - 9 Sep
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
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
Adorable Cottage, 5 min walk to water & town
Exterior

3. 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 AED 634
AED 1,229 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Lakefront Tiny House
Beach nearby

4. 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 AED 653
AED 1,459 total
includes taxes & fees
8 Sep - 9 Sep
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Interior

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 AED 1,396
AED 2,518 total
includes taxes & fees
14 Sep - 15 Sep
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
1 bedroom, WiFi (free), bed sheets

6. 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 AED 719
AED 1,334 total
includes taxes & fees
13 Sep - 14 Sep
Lakefront Boho Tiny House
Sun loungers, beach towels

7. 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 AED 578
AED 1,344 total
includes taxes & fees
24 Aug - 25 Aug
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Private kitchen

8. 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 AED 808
AED 1,712 total
includes taxes & fees
16 Aug - 17 Aug
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Dining

9. 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.
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
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 AED 1,216
AED 2,762 total
includes taxes & fees
9 Sep - 10 Sep
Beachside Bliss w/ Game Room, Gym & Golf Green
Exterior

11. 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 AED 2,217
AED 3,580 total
includes taxes & fees
18 Aug - 19 Aug
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Coffee/tea maker, microwave, oven, stovetop

12. 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 AED 1,028
AED 1,994 total
includes taxes & fees
16 Aug - 17 Aug
Entire Vacation Home in Waterford Connecticut
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.
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 AED 1,693
AED 2,800 total
includes taxes & fees
20 Aug - 21 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 AED 914
AED 1,960 total
includes taxes & fees
8 Sep - 9 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, (177 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 AED 496
AED 909 total
includes taxes & fees
18 Aug - 19 Aug
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Flat-screen TV

18. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (46 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is AED 1,167
AED 1,333 total
includes taxes & fees
7 Sep - 8 Sep
North Fork Resort
Condo | Terrace/patio

19. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (282 reviews)
"Great place!"
United States
Christine
The price is AED 1,126
AED 1,614 total
includes taxes & fees
9 Sep - 10 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
"Booked “King Room” for 3-people - checked/selected 3-people in the box, keeping in mind there will be extra bed (sofa, or roll away bed prepaired-ready to use for 3-rd person). Check in was 3-PM, drove from Burlington VT (4.5 hrs), coming to hotel around 2-PM, called at 1-PM from road asking for early 2-PM check in, not granted! So, went to Newport, RI, came to hotel before 9-PM, and got room with ONE king bed, nothing more for 3-rd person (15-yrs old grandson). Asked for help, called front desk 2x, went to front desk 3x, asking: please, help! Need two beds room, or extra bed! Answer: we all booked out. 2-people at front desk were not really interested in helping, showing they are busy, looking into screens. Finally, tired after the long day, the gentleman came in, and set up roll away bed around 11-PM!!, for $35 extra money. This should be included. Paid $369 with breakfast for 3, plus $35 for rollaway bed. Decided do not complaint, next time won’t go there. Breakfast prepaid, simple menu ala carte, nothing special, hotel OK, lower class hotel, but.. not cheap! Close to Foxwood Casino, but not interested in it."
Tad 1-night trip
Posted 10 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.