Old Saybrook Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14

Vacation Rentals in Old Saybrook

adorable ranch in beach community
Beach nearby

adorable ranch in beach community

9.8 out of 10, Exceptional, (46)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is ￥32,351
￥70,363 total
includes taxes & fees
Sep 22 - Sep 23
adorable ranch in beach community
Postcard Cabins Machimoodus
Standard Cabin, 1 Queen Bed | Exterior

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (56)
"Great stay"
The price is ￥18,969
￥27,733 total
includes taxes & fees
Sep 1 - Sep 2
Postcard Cabins Machimoodus
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (239)
"Had a great time. Will be back"
The price is ￥48,768
￥62,107 total
includes taxes & fees
Sep 11 - Sep 12
Cliffside Resort Condominiums
Charming houseboat in pleasant New London with AC, WiFi
Interior

Charming houseboat in pleasant New London with AC, WiFi

9.6 out of 10, Exceptional, (10)
"Very nice people. Boat was roomy and well stocked but dirty. Toilet pump was broken and made loud noises all night. We were not informed this was an issue til checkout. Some other small issues "
The price is ￥22,058
￥47,571 total
includes taxes & fees
Sep 1 - Sep 2
Charming houseboat in pleasant New London with AC, WiFi
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Property grounds

Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

8.0 out of 10, Very Good, (9)
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Amazing Ocean Front 2 Story Home, Steps Away From The Water
Outdoor dining

Amazing Ocean Front 2 Story Home, Steps Away From The Water

9.8 out of 10, Exceptional, (97)
"This is our 2nd time renting the home and we have booked for a third. Cindy is a fantastic host and her beach house is a perfect getaway. Family enjoyed every minute. "
Amazing Ocean Front 2 Story Home, Steps Away From The Water
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (93)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
2 bedrooms, iron/ironing board, free WiFi, bed sheets

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

10.0 out of 10, Exceptional, (1)
"We visited here for a weekend in the Mystic area. Our daughter joined us for an evening and the home was cozy and comfortable for 3 adults. The check in process was seamless and communication with the host was always timely. They thought of everything to make our stay enjoyable and everything was within arms reach. The home is located in a great spot and enabled us to enjoy many surrounding areas. Pawcatuck/Westerly, Mystic, Watch Hill... all were very close so this was a perfect base of...
The price is ￥25,734
￥52,387 total
includes taxes & fees
Sep 28 - Sep 29
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is ￥10,233
￥27,345 total
includes taxes & fees
Sep 4 - Sep 5
The Stern at Soundview · Beach+Ocean+Sunrise
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is ￥36,763
￥59,041 total
includes taxes & fees
Sep 2 - Sep 3
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (141)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
The Mast at Soundview · Beach+Ocean+Sunrise
On the beach

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is ￥10,613
￥27,781 total
includes taxes & fees
Sep 2 - Sep 3
The Mast at Soundview · Beach+Ocean+Sunrise
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
1 bedroom, WiFi, bed sheets

Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

10.0 out of 10, Exceptional, (5)
The price is ￥13,235
￥18,161 total
includes taxes & fees
Sep 1 - Sep 2
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
Thames River Retreat · CT College+Casinos+USCGA
Property grounds

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (9)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is ￥42,430
￥104,038 total
includes taxes & fees
Sep 1 - Sep 2
Thames River Retreat · CT College+Casinos+USCGA
Shoreline Oasis
Exterior

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is ￥26,322
￥38,762 total
includes taxes & fees
Sep 1 - Sep 2
Shoreline Oasis
The Crow's Nest at the Blue Anchor. Ready for 2025
Property grounds

The Crow's Nest at the Blue Anchor. Ready for 2025

2.0 star property
10.0 out of 10, Exceptional, (11)
"Nice to come home to a welcoming place with well-outfitted kitchen ready to cook breakfast!"
The Crow's Nest at the Blue Anchor. Ready for 2025
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Property grounds

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

10.0 out of 10, Exceptional, (25)
"Very nice rooms staff go above and beyond with the little things to make you're experience awesome "
The price is ￥12,626
￥26,762 total
includes taxes & fees
Sep 2 - Sep 3
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Coastal Retreat • 2BR Near Beaches & Mystic
Private kitchen

Coastal Retreat • 2BR Near Beaches & Mystic

10.0 out of 10, Exceptional, (3)
"Nice clean place, has everything you need and is in a great location!"
The price is ￥30,439
￥53,717 total
includes taxes & fees
Sep 1 - Sep 2
Coastal Retreat • 2BR Near Beaches & Mystic
Escape to a cozy château in Lambert’s Cove, Stonington, CT.
1 bedroom, WiFi, bed sheets

Escape to a cozy château in Lambert’s Cove, Stonington, CT.

10.0 out of 10, Exceptional, (1)
"Great weekend stay, clean and comfortable. Located in a great area if you plan to go out too! "
Escape to a cozy château in Lambert’s Cove, Stonington, CT.
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Dining

The Mystic Harbor House · walk downtown Mystic · train · aquarium

10.0 out of 10, Exceptional, (4)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
The price is ￥54,391
￥101,379 total
includes taxes & fees
Sep 1 - Sep 2
The Mystic Harbor House · walk downtown Mystic · train · aquarium
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.
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

Find out more about Old Saybrook

Find out more about Old Saybrook

Search for holiday rentals in Old Saybrook on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Saybrook using one of the methods below:

  • View our selection of featured holiday rentals in Old Saybrook
  • Use the map to find apartments and other holiday homes in the Old Saybrook neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Old Saybrook while they last

Look no further and take a look at our great range of rental properties in Old Saybrook!

Explore a world of travel with Expedia

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 Saybrook Country Barn, 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?

Adorable ranch in beach community: Visitors like this Old Saybrook vacation home rental. It is located near the beach and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Old Saybrook?

Choose from 58 Expedia vacation rentals in Old Saybrook for a memorable vacation.

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

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