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Holiday homes in Old Saybrook You’ll Love

Top-Rated Old Saybrook Holiday homes for Every Budget and Style!

Looking for a holiday home in Old Saybrook (Connecticut)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Old Saybrook.

We found 10 Holiday-homes in Old Saybrook and the surrounding area (within 40 miles)

Charming Old Saybrook Cottage Less Than 1 Mi to Beach in Old Saybrook, USA

Charming Old Saybrook Cottage Less Than...

Holiday home in Old Saybrook, Connecticut
Charming Old Saybrook Cottage Less Than 1 Mi to Beach is located in Old Saybrook, just 29 miles from Thimble Islands and 29 miles from Wesleyan Univer...
  • Parking

Exceptional 2 Reviews 10.0

from $394.07 Show details »

Cozy Westbrook Vacation Rental - Walk to Beach! in Westbrook, USA

Cozy Westbrook Vacation Rental - Walk to...

Holiday home in Westbrook near Old Saybrook, Connecticut
Cozy Westbrook Vacation Rental - Walk to Beach! is located in Westbrook, just 16 miles from Goodspeed Opera House and 24 miles from Thimble Islands.
  • Parking

Fabulous 3 Reviews 9.0

from $323.15 Show details »

Charming Westbrook Cottage, Steps to Private Beach in Westbrook, USA

Charming Westbrook Cottage, Steps to Pri...

Holiday home in Westbrook near Old Saybrook, Connecticut
Charming Westbrook Cottage, Steps to Private Beach offers accommodations in Westbrook, 18 miles from Goodspeed Opera House and 25 miles from Thimble I...
  • Parking
  • Pets allowed

Pleasant 3 Reviews 6.7

from $269.87 Show details »

Great Hammcock Getaway in Old Saybrook, USA

Great Hammcock Getaway

Holiday home in Old Saybrook, Connecticut , 129 Great Hammock Road
Great Hammcock Getaway is a recently renovated vacation home in Old Saybrook where guests can make the most of the free bikes and barbecue facilities.
  • Parking
  • Family rooms

Superb 8 Reviews 9.4

from $91.00 Show details »

Westbrook Home with Ocean Views - Walk to Beach in Westbrook, USA

Westbrook Home with Ocean Views - Walk t...

Holiday home in Westbrook near Old Saybrook, Connecticut
Westbrook Home with Ocean Views - Walk to Beach is located in Westbrook, just 23 miles from Thimble Islands and 26 miles from Wesleyan University.
  • Parking

Poor 1 Reviews 3.0

from $406.94 Show details »

Grandmas Cottage with Sunroom Walk to Beach in Old Saybrook, USA

Grandmas Cottage with Sunroom Walk to Be...

Holiday home in Old Saybrook, Connecticut
Grandmas Cottage with Sunroom Walk to Beach offers accommodations in Old Saybrook, 16 miles from Goodspeed Opera House and 25 miles from Thimble Islan...
  • Parking
  • Pets allowed

no reviews

from $215.54 Show details »

Charming Old Lyme Cottage, Steps to Private Beach! in Old Lyme, USA

Charming Old Lyme Cottage, Steps to Priv...

Holiday home in Old Lyme near Old Saybrook, Connecticut
Charming Old Lyme Cottage, Steps to Private Beach! offers accommodations in Old Lyme, 22 miles from Mystic Seaport and 28 miles from Foxwoods Casinos.
  • Parking

Good 8 Reviews 7.7

from $321.23 Show details »

Captain Nataniel Clarke Historic Homestead in Old Saybrook, USA

Captain Nataniel Clarke Historic Homeste...

Holiday home in Old Saybrook, Connecticut , 1200 Boston Post Road
Captain Nataniel Clarke Historic Homestead is located in Old Saybrook, just 16 miles from Goodspeed Opera House and 25 miles from Thimble Islands.
  • Parking

no reviews

from $58.00 Show details »

Sandy Feet Retreat - Walk To Beach! in Old Lyme, USA

Sandy Feet Retreat - Walk To Beach!

Holiday home in Old Lyme near Old Saybrook, Connecticut , 32 Portland Avenue
Sandy Feet Retreat - Walk To Beach! offers accommodations in Old Lyme, 19 miles from Goodspeed Opera House and 22 miles from Mystic Seaport.
  • Parking
  • Family rooms

no reviews

from $88.00 Show details »

Historic Essex Home with Large Yard Near Downtown! in Essex, USA

Historic Essex Home with Large Yard Near...

Holiday home in Essex near Old Saybrook, Connecticut
Historic Essex Home with Large Yard Near Downtown! is located in Essex, just 10 miles from Goodspeed Opera House and 21 miles from Wesleyan University...
  • Parking
  • Spa and wellness centre

Exceptional 16 Reviews 9.5

from $190.08 Show details »

Number of Holiday homes in Old Saybrook 10
Number of guest ratings 1,957
Average price per night $515.00
Lowest price per night $50,00
Highest price per night $4.871,01

Top 10 Cheapest Holiday-homes in Old Saybrook

Discover the Cheapest Holiday-homes in Old Saybrook – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Old Saybrook

Check out the Most Booked Holiday-homes in Old Saybrook – Based on Guest Popularity.

Holiday homes in Old Saybrook (Connecticut), comfortable and familiar

Staying in a holiday or vacation home in Old Saybrook can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Old Saybrook for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Old Saybrook should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com