Old Saybrook Vacation Rentals

Compare 243 available properties from 14 providers
Old Saybrook
Save up to 47%

Best Vacation Home Deals in Old Saybrook

-19%
e.g. 10/13 - 10/20
House ∙ 7 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $269 $333
VRBO
4.7
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-30%
e.g. 10/27 - 11/3
House ∙ 2 guests ∙ 1 bedroom
Old Saybrook, Middlesex County, Connecticut, United States
from $123 $175
VRBO
4.8
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-47%
e.g. 11/24 - 12/1
House ∙ 4 guests ∙ 1 bedroom
Old Saybrook, Middlesex County, Connecticut, United States
from $111 $209
VRBO
4.0
View deal

Find a dreamlike vacation rental from $59 per night by exploring the 243 properties available in Old Saybrook. Using HomeToGo you can directly compare the prices of each available property to find the best price and save up to 47%.

Recommended Vacation Rentals in Old Saybrook

Rent a vacation accommodation in Old Saybrook: from $59 per night

House ∙ 4 guests ∙ 1 bedroom
Old Saybrook, Middlesex County, Connecticut, United States
from $111
VRBO
4.0
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House ∙ 5 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $147
VRBO
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $202
VRBO
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $165
VRBO
5.0
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House ∙ 6 guests ∙ 2 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $155
VRBO
5.0
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Apartment ∙ 4 guests ∙ 1 bedroom
Old Saybrook, Middlesex County, Connecticut, United States
from $112
VRBO
4.5
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House ∙ 6 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $277
VRBO
5.0
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House ∙ 6 guests ∙ 2 bedrooms
Westbrook Center, Westbrook, Connecticut, United States
from $329
VRBO
5.0
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 5 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $118
VRBO
4.8
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Fishing
House ∙ 7 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $250
VRBO
4.7
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Fishing
House ∙ 2 guests ∙ 1 bedroom
Old Saybrook, Middlesex County, Connecticut, United States
from $123
VRBO
4.8
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Fishing
House ∙ 6 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $150
VRBO
5.0
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Vacation Rentals With a Fireplace

Fireplace
House ∙ 4 guests ∙ 1 bedroom
Old Saybrook, Middlesex County, Connecticut, United States
from $187
VRBO
4.5
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $145
VRBO
5.0
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Fireplace
House ∙ 7 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $445
VRBO
5.0
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Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $299
Booking.com
4.5
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Apartments With a Balcony or Patio

Balcony/Patio
House ∙ 6 guests ∙ 2 bedrooms
Old Lyme, New London County, Connecticut, United States
from $151
VRBO
5.0
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Balcony/Patio
House ∙ 8 guests ∙ 4 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $315
VRBO
5.0
View deal
Balcony/Patio
House ∙ 8 guests ∙ 4 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $153
VRBO
4.8
View deal
Balcony/Patio
House ∙ 8 guests ∙ 4 bedrooms
Old Saybrook, Middlesex County, Connecticut, United States
from $236
VRBO
5.0
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Popular Rental Amenities in Old Saybrook

  • Internet (203)
  • No smoking (201)
  • Parking (200)
  • TV (191)
  • Kitchen (183)
  • Microwave (169)
  • AC (158)
  • Grill (146)
  • Yard (132)
  • Fishing (131)
  • No pets (117)
  • Washer (103)
Filters are conveniently available so you can find the ideal vacation rental in Old Saybrook. In Old Saybrook, 201 rentals offer "internet". So, if you need internet access during your vacation, use the internet filter to compare these rentals. Three features that are not common are "saunas," "Jacuzzis," and "pools."

The Weather in Old Saybrook

39°
25°
39°
25°
46°
32°
57°
39°
70°
52°
75°
59°
82°
66°
81°
64°
73°
57°
63°
46°
52°
37°
45°
32°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for Old Saybrook. July is the warmest month in Old Saybrook with average maximum temperatures of 82°. On the contrary, the coolest month is January. The month of November has nice weather with only 9 rainy days.

173 out of the 243 listed rentals in Old Saybrook are house rentals. They account for two-thirds of the accommodation options in this destination (71.49%). In addition, these properties have an average size of 1,680 ft² and an average price of $345 a night. Furthermore, if you are going in a group of 8, house rentals are an excellent accommodation type in Old Saybrook, as they usually accommodate this exact group size. Vacationers looking for something other than house rentals can also find many bed & breakfast rentals, which are the second most popular accommodation option in Old Saybrook. While house rentals in Old Saybrook have an average size of 1,680 ft², bed & breakfast rentals have an average size of 310 ft².

Exploring New England's beauty: a vacation rental in Old Saybrook

As one of the oldest towns in Connecticut, Old Saybrook is home to historical sites dating back to English colonial times. A vacation rental in Old Saybrook offers beautiful views of the marina and beyond.

Show all 243 properties
Food & Drinks

New England cusine at its elegant best

When in New England, your trip is incomplete without a taste of the finest oysters and seafood in the country. Old Saybrook is home to Liv's Oyster Bar & Restaurant, which is an absolute favorite among locals and visitors.The clams, monkfish, and other locally-sourced dishes that stand out among the other fried seafood establishments.

Breakfast and brunch fans also have many options, the best of which is Mirsina's, a greek-inspired restaurant offering delicious omelettes, eggs benedict, greek salad fresh bread and vegetable dishes. The portions are huge and the food delicious.

Art & Culture

Art and culture at its finest: exploring the rich history of Old Saybrook

If you or your family are fans of performance art, Old Saybrook will not disappoint you. The most famous spot for all cultural events is the Katherine Hepburn Cultural Arts Center, which has been around since 1905.

In addition to a museum dedicated to the history of Katherine Hepburn's life, the Center also hosts concerts and theater productions as well as an entire children's series and a camp for kids.

Another great option for families with children is Treehouse Players, which creates a fun environment for children to explore theater, dialogue, music, and improvised movement.

Local Events

Annual events at Old Saybrook

There's no better way to explore a town's history than by attending the regular events held there every year. Old Saybrook hosts an Annual Arts & Crafts Festival each July, which proudly welcomes over 150 artists and crafters and 10.000 visitors.

If stained glass, quilts, pottery, sculpture, jewelry, photography, leather, painting, acrylic, wood carving and more sound appealing to you, July is the best time to visit good Old Saybrook!

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Old Saybrook VRBO Vacation Rentals in Old Saybrook HomeAway Vacation Rentals in Old Saybrook TripAdvisor Vacation Rentals in Old Saybrook VacationRentals.com Vacation Rentals in Old Saybrook HouseTrip Vacation Rentals in Old Saybrook FlipKey Vacation Rentals in Old Saybrook Wimdu Vacation Rentals in Old Saybrook 9flats.com Vacation Rentals in Old Saybrook VaycayHero Vacation Rentals in Old Saybrook PerfectPlaces.com Vacation Rentals in Old Saybrook Homestay.com Vacation Rentals in Old Saybrook only-apartments Vacation Rentals in Old Saybrook Interhome Vacation Rentals in Old Saybrook Bedycasa Vacation Rentals in Old Saybrook Novasol Vacation Rentals in Old Saybrook HomeEscape Vacation Rentals in Old Saybrook

Vacation Destinations Near Old Saybrook