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

Old Saybrook Vacation Rentals

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

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Old Saybrook vacation rentals

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

1. 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.
$374 nightly
The price is $427
Sep 27 - Sep 28
Total with taxes and fees
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

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.
$392 nightly
The price is $447
Sep 28 - Sep 29
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.

3. 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.
$466 nightly
The price is $532
Sep 28 - Sep 29
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

4. 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.
$436 nightly
The price is $497
Sep 27 - Sep 28
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
A spacious room with a large dining table and chairs, a sofa, and large windows offering a view of the sea and buildings.

5. 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, (42 reviews)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

6. 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.
$563 nightly
The price is $641
Oct 20 - Oct 21
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

7. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
$199 nightly
The price is $226
Oct 26 - Oct 27
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A beach with waves, a clear sky, and a sandy shore.

8. 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.
$353 nightly
The price is $402
Sep 29 - Sep 30
Total with taxes and fees
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
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, (10 reviews)
"Every thing was amazing "
United States
Annaliaa C.
$240 nightly
The price is $273
Oct 20 - Oct 21
Total with taxes and fees
Lakefront Boho Tiny House
A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

10. 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.
$411 nightly
The price is $468
Sep 28 - Sep 29
Total with taxes and fees
Direct Lakefront - Stunning Views and Panoramic Sunsets
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

11. 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)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$253 nightly
The price is $287
Oct 7 - Oct 8
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

12. 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.
$272 nightly
The price is $310
Oct 6 - Oct 7
Total with taxes and fees
Cozy Lakefront Tiny House
A living room with a dark grey sofa, two wooden chairs, a small table with a tray, and a large window with a view of the sea.

13. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (96 reviews)
"Unbeatable views and professional hosts."
United States
Russell A.
$933 nightly
The price is $1,064
Sep 28 - Sep 29
Total with taxes and fees
Direct waterfront renovated cottage.
A beach with waves, a clear sky, and a sandy shore.

14. 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.
$269 nightly
The price is $305
Sep 29 - Sep 30
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A beach with a house in the background, a clear sky, and a calm sea.

15. 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.
$291 nightly
The price is $331
Oct 6 - Oct 7
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A wooden deck with a red chair and a table, a tent, and a grassy area in the background.

16. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
$270 nightly
The price is $308
Oct 1 - Oct 2
Total with taxes and fees
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
A cabin with a dining table set for two, a bicycle, and a small porch area.

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, (192 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
$167 nightly
The price is $192
Oct 1 - Oct 2
Total with taxes and fees
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, (58 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$258 nightly
The price is $294
Oct 27 - Oct 28
Total with taxes and fees
North Fork Resort

19. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (294 reviews)
"Great place!"
United States
Christine
$333 nightly
The price is $380
Oct 25 - Oct 26
Total with taxes and fees
Cliffside Resort Condominiums
A two-story house with a front porch, a balcony, and a driveway.

20. Grey comfort room

Grey comfort room
New London
9.6 out of 10, Exceptional, (4 reviews)
"Nice place"
United States
JACQUELINE FELICIANO
$104 nightly
The price is $116
Sep 28 - Sep 29
Total with taxes and fees
Grey comfort room
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

New Haven Hotel

New Haven Hotel

8/10 Good
"The staff members at check-in & check-out were warmly professional and attentive. What a gorgeous & spacious living room area with appealing decor. The breakfast options were fantastic for self-serve options. The room was immaculate. Two points that led me to rate it a 4.7 out of 5 = the extremely hard bed & non-working light & electric fixtures on the side of the bed by the window."
Maria Luisa 1-night trip
Posted 9 hours ago
New Haven Hotel

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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.