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

Old Saybrook Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Old Saybrook vacation 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, (61 reviews)
"We enjoyed our stay"
United States
JM B.
$185 nightly
The price is $209
Oct 18 - Oct 19
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

2. 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, (15 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
$398 nightly
The price is $451
Oct 12 - Oct 13
Total with taxes and fees
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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.
$303 nightly
The price is $344
Nov 3 - Nov 4
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

4. 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.
$417 nightly
The price is $472
Oct 15 - Oct 16
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
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.
$497 nightly
The price is $563
Oct 21 - Oct 22
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

6. 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, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$265 nightly
The price is $299
Oct 13 - Oct 14
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A single bed with a patterned pillow and a quilt, a wooden nightstand with a decorative item, and a wooden wall with a window.

7. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
$251 nightly
The price is $284
Oct 11 - Oct 12
Total with taxes and fees
Westbrook Getaway-Near Beaches, Train & Shoreline
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

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.
$253 nightly
The price is $286
Nov 4 - Nov 5
Total with taxes and fees
Cozy Lakefront Tiny House
A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

9. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"Every thing was amazing "
United States
Annaliaa C.
$238 nightly
The price is $270
Nov 3 - Nov 4
Total with taxes and fees
Lakefront Boho Tiny House
A small, clean room with a glass door leading outside, a round table with two chairs, and a window providing a view of the outside.

10. Cozy Queen Bed Room |Free Parking

Cozy Queen Bed Room |Free Parking
East Lyme
$78 nightly
The price is $90
Nov 1 - Nov 2
Total with taxes and fees
Cozy Queen Bed Room |Free Parking
A hotel lobby with a reception desk, a television mounted on the wall, a small seating area with chairs, and a window providing a view outside.

11. Cozy 2 Full Beds | Smoking Wifi

Cozy 2 Full Beds | Smoking Wifi
Niantic
$81 nightly
The price is $93
Nov 1 - Nov 2
Total with taxes and fees
Cozy 2 Full Beds | Smoking Wifi
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

12. 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.
$548 nightly
The price is $621
Nov 3 - Nov 4
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
A beach with a house in the background, a clear sky, and a calm sea.

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.
$322 nightly
The price is $364
Oct 20 - Oct 21
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A beach with waves, a clear sky, and a sandy shore.

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.
$412 nightly
The price is $467
Nov 3 - Nov 4
Total with taxes and fees
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

15. Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"Very peaceful and quiet. Beautiful view of the lake. Would definitely book again."
United States
James C.
$373 nightly
The price is $422
Oct 18 - Oct 19
Total with taxes and fees
Direct Lakefront - Stunning Views and Panoramic Sunsets
A hotel reception area with a red wall, a digital clock, and a sign indicating room rates are updated.

16. Sunny 1 Queen Bed Smk Free Parking

Sunny 1 Queen Bed Smk Free Parking
Niantic
$78 nightly
The price is $90
Nov 1 - Nov 2
Total with taxes and fees
Sunny 1 Queen Bed Smk Free Parking
A hotel room with two beds, a desk, a chair, and a bathroom visible through an open door.

17. Cozy 2 Full Beds|Free Parking & Wifi

Cozy 2 Full Beds|Free Parking & Wifi
Niantic
$81 nightly
The price is $93
Nov 1 - Nov 2
Total with taxes and fees
Cozy 2 Full Beds|Free Parking & Wifi
A person at a desk with a telephone, a notepad, and a wall with a number sign.

18. Cozy Queen Bed | Micfridge, Smoking

Cozy Queen Bed | Micfridge, Smoking
Niantic
$83 nightly
The price is $95
Nov 1 - Nov 2
Total with taxes and fees
Cozy Queen Bed | Micfridge, Smoking
A motel with a two-story structure, a covered parking area, and a clear sky.

19. Spacious 2-bed | Free Parking & Wifi

Spacious 2-bed | Free Parking & Wifi
Niantic
$85 nightly
The price is $98
Nov 1 - Nov 2
Total with taxes and fees
Spacious 2-bed | Free Parking & Wifi
A cabin with a dining table set for two, a bicycle, and a small porch area.

20. 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, (201 reviews)
"Great experience and the perfect environment"
United States
Stephanie
$175 nightly
The price is $201
Nov 9 - Nov 10
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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

Two Trees Inn

Two Trees Inn

10/10 Excellent
"Beautiful property! Quaint, quiet and clean! Staff was very pleasant and the breakfast had a lot of choices. Few dollars more than the basic hotels, but not by a crazy amount. Well worth the extra few dollars!"
JoAnne 1-night trip
Posted 1 hour ago
Two Trees Inn

Find out more about Old Saybrook

Everything you need to know about Old Saybrook vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Old Saybrook vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Saybrook vacation 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 low season months. For more hustle and bustle, you may prefer to visit Old Saybrook in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $201 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Old Saybrook rentals

At Expedia, we put the best Old Saybrook vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.