A coastal town with a lighthouse, houses, and a river.

Old Saybrook Vacation Rentals

Q: 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.

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Dates

November 2026

December 2026

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Our top choices for Old Saybrook vacation rentals

A wooden counter with a Dove beauty bar, Tommy Hilfiger towels, and a black hair dryer bag.

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

Clinton

Marcy C.

$206 nightly

Nov 11 - Nov 12

Total with taxes and fees

A hotel room with a bed, a nightstand, a wall-mounted lamp, and a window with curtains.

2. Sunny 1 Queen Bed Smk Free Parking

Niantic

Anonymous traveler

$78 nightly

Nov 12 - Nov 13

Total with taxes and fees

A beach with waves, a clear sky, and a sandy shore.

3. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Westbrook Center

Mason T.

$260 nightly

Nov 11 - Nov 12

Total with taxes and fees

A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

4. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Saybrook Manor

Alexis L.

$482 nightly

Nov 16 - Nov 17

Total with taxes and fees

A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

5. Lakefront Boho Tiny House

East Lyme

Linda M.

$217 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

6. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Old Saybrook

Karol T.

$399 nightly

Nov 15 - Nov 16

Total with taxes and fees

A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

7. Cozy Lakefront Tiny House

East Lyme

Richard R.

$230 nightly

Nov 11 - Nov 12

Total with taxes and fees

A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

8. The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton

Wink V.

$300 nightly

Nov 11 - Nov 12

Total with taxes and fees

A hotel reception area with a counter, a digital tablet, and a poster on the wall.

9. Cozy 2 Full Beds | Smoking Wifi

Niantic

Anonymous traveler

$81 nightly

Nov 15 - Nov 16

Total with taxes and fees

An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

10. Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook

Morgan M.

$533 nightly

Dec 1 - Dec 2

Total with taxes and fees

A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

11. Adorable Cottage with Cottage porch, walk to water & town

Westbrook Center

Francine F.

$497 nightly

Nov 11 - Nov 12

Total with taxes and fees

A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

12. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Center

$355 nightly

Dec 1 - Dec 2

Total with taxes and fees

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!

Madison

Samantha D.

$252 nightly

Nov 15 - Nov 16

Total with taxes and fees

A hotel reception area with a receptionist, a guest, and a child.

14. Cozy 2 Full Beds|Free Parking & Wifi

Niantic

Anonymous traveler

$81 nightly

Nov 11 - Nov 12

Total with taxes and fees

A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

15. Direct Lakefront - Stunning Views and Panoramic Sunsets

East Lyme

James C.

$503 nightly

Nov 23 - Nov 24

Total with taxes and fees

16. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

Westbrook Center

Dorothy W.

$345 nightly

Nov 11 - Nov 12

Total with taxes and fees

17. Cozy Queen Bed Room |Free Parking

East Lyme

Anonymous traveler

$78 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern living room with a large TV, white cabinetry, and a view of the outdoors.

18. Charming beach home, complete with pool & cozy guest house!

Clinton

Juliana A.

$1,042 nightly

Nov 12 - Nov 13

Total with taxes and fees

19. Spacious 2-bed | Free Parking & Wifi

Niantic

Anonymous traveler

$85 nightly

Nov 11 - Nov 12

Total with taxes and fees

20. Cozy 2 Full Beds | ADA/Tub

Niantic

Anonymous traveler

$81 nightly

Nov 25 - Nov 26

Total with taxes and fees

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Find vacation rentals that suit your style

Top Old Saybrook Hotel Reviews

A wooden pathway leading to beach chairs and umbrellas, surrounded by lush greenery and a view of the sea.

Silver Sands Motel & Beach Bungalows

Greenport

10/10 Excellent

Nicole

A spacious dining area with multiple tables and chairs, large windows with a marina view, and a modern kitchen with white cabinetry.

Inn at Harbor Hill Marina

Niantic

10/10 Excellent

NianticQuaint

A living room with a stone fireplace, grey sofas, and a coffee table.

The Captain Stannard

Westbrook Center

10/10 Excellent

Julie

A view from a covered deck with two Adirondack chairs and a small table, overlooking a marina with boats and a rocky shoreline.

Harbor View Landing

West Mystic

10/10 Excellent

Ruiyi

A marina at sunset with boats docked, a fire feature on the deck, and a chair.

Saybrook Point Resort & Marina

Old Saybrook Center

10/10 Excellent

Robin

A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

Westbrook Inn B&B

Westbrook Center

10/10 Excellent

david

A dining table with a salad, breaded fish, and drinks.

The Hotel Maria

Misquamicut

10/10 Excellent

Great location and the hotel is very clean and in excellent condition. Thought the price was high for the time of year (mid- Oct). We were just there for a night so I thought it was crazy that we had to pay a resort fee considering the restaurant was not open and we were told we had to be out by 11:00am because they were closing the hotel for the week. Other than that the staff was friendly and we enjoyed our stay.

CAS

A multi-story hotel with balconies and a beach view.

Madison Beach Hotel

Madison Center

10/10 Excellent

Donald

An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.

Home2 Suites by Hilton East Haven New Haven

The Centre

10/10 Excellent

Daniel

A two-story house with a balcony on the second floor.

The Taber Inne & Suites

Mystic

10/10 Excellent

Robert

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

The Menhaden

Greenport

10/10 Excellent

Anonymous traveler

A cabin with a dining table set for two, a bicycle, and a small porch area.

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

10/10 Excellent

Marcus

A restaurant with wooden beams, large windows, and blue chairs. Tables are set with wine glasses and cutlery.

The Whaler's Inn

Mystic

10/10 Excellent

James

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

The Shoals Suites and Slips

Southold

10/10 Excellent

Andrew

A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.

Hotel Marcel New Haven, Tapestry Collection By Hilton

Long Wharf

10/10 Excellent

Matthew

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 $89 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.

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.

Explore a world of travel with Expedia

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Old Saybrook Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Old Saybrook vacation rentals

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

2. Sunny 1 Queen Bed Smk Free Parking

3. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

4. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

5. Lakefront Boho Tiny House

6. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

7. Cozy Lakefront Tiny House

8. The gardners Cottage 1 mile from long Island Sound - pet friendly

9. Cozy 2 Full Beds | Smoking Wifi

10. Beachside Bliss w/ Game Room, Gym & Golf Green

11. Adorable Cottage with Cottage porch, walk to water & town

12. Westbrook Getaway-Near Beaches, Train & Shoreline

13. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

14. Cozy 2 Full Beds|Free Parking & Wifi

15. Direct Lakefront - Stunning Views and Panoramic Sunsets

16. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

17. Cozy Queen Bed Room |Free Parking

18. Charming beach home, complete with pool & cozy guest house!

19. Spacious 2-bed | Free Parking & Wifi

20. Cozy 2 Full Beds | ADA/Tub

Find vacation rentals that suit your style

Top Old Saybrook Hotel Reviews

Silver Sands Motel & Beach Bungalows

10/10 Excellent

Find out more about Old Saybrook

Everything you need to know about Old Saybrook vacation rentals

Old Saybrook vacation rentals: An excellent choice for every season

How to find incredible deals on Old Saybrook rentals

Frequently Asked Questions

Can I find a vacation rental in Old Saybrook?

What are some of the best vacation home rentals in Old Saybrook?

How many vacation rentals will I find in Old Saybrook?

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

What’s a vacation rental in Old Saybrook like?

Explore a world of travel with Expedia