Old Saybrook Vacation Rentals

See all 68 deals in Old Saybrook

Our Favorite Vacation Rentals in Old Saybrook

  • The Sharlene Cottage
     Country House
    Booking.com
    From
    $350
  • Marina Point Villas at Saybrook Point
     2br Country House
    HolidayLettings
    From
    $1,435
  • The Peace Barn Sanctuary
     Country House
    Booking.com
    From
    $165
  • NEW! Saybrook Manor House, Walk to Cove Beach!
     3br Home/Apartment
    HolidayLettings
    From
    $433
  • Oceanfront, Private Beach
     Country House
    Booking.com
    From
    $1,015
  • Updated Old Lyme Cottage - Steps from the Beach!
     3br Cottage
    HolidayLettings
    From
    $277
  • Exceptional Hilltop Orchard Estate
     Villa
    Booking.com
    From
    $1,246
  • Luxurious living on a bucolic alpaca farm
     2br Home/Apartment
    HolidayLettings
    From
    $339

Check prices for these upcoming dates

Old Saybrook Vacation Rentals with a Pool

  • Convenient and Cute in Downtown Old Saybrook
    ExcellentHome/Apartment
    Airbnb
    From
    $126
  • Large Waterfront House with Pool
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,356
  • Quiet setting for this guesthouse with pool.
    ExcellentHome/Apartment
    Airbnb
    From
    $170
  • Winterwood Country Estate - 26 Scenic Acres
    Excellent3br Home/Apartment
    Airbnb
    From
    $655

Old Saybrook Vacation Rentals with Wi-Fi

  • ⚓Captain Clarke Homestead⚓✨ buy 2/1 free
    Excellent5br Home/Apartment
    Airbnb
    From
    $622
  • White House on Oldsaybrook Ct.
    Excellent3br Home/Apartment
    Airbnb
    From
    $137
  • The Cottage
    GoodHome/Apartment
    Airbnb
    From
    $134
  • Astro's Place - shoreline suite with a view!
    ExcellentHome/Apartment
    Airbnb
    From
    $154

Old Saybrook Pet-Friendly Vacation Rentals

  • Steps to beach 4bd 2 bth Sleeps 14
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $714
  • Peace Barn in the heart of the CT River Valley
     4br Home/Apartment
    HolidayLettings
    From
    $311
  • 3 Room Eco-Friendly Suite in Historic 1790 Home
    Excellent3br Home/Apartment
    Airbnb
    From
    $316
  • Peace Barn in the heart of the CT River Valley
    Good5br Home/Apartment
    Airbnb
    From
    $271

Old Saybrook Travel Guide

Full of charm, history, picturesque views and the kind of quintessential American town atmosphere that Hollywood loves, Old Saybrook is a delightful Connecticut coastal town, and it's also one of the oldest.

Things to Do in Old Saybrook

Classic buildings and houses adorn the waterfront downtown, so feel free to stroll the streets and get the vintage vibe with old signs depicting the Saybrook Hardware Co., Old Colony Package Store and others. Discover boutique clothes and shoes, antiques and gifts in several one-of-a-kind shops.Outdoor enthusiasts can enjoy running, fishing and kayaking along the wilderness area of the Connecticut River or wander the boats in the harbor and enjoy the sea views from the beaches or walk towards the Lynde Point Lighthouse for atmospheric photos at sunset. There's plenty of great places to eat seafood and enjoy craft beers here with wonderful coastal views.

Best Time to Visit Old Saybrook

Summer brings crowds enjoying the beach and boating opportunities, fall can be spectacular with that lovely New England fall atmosphere as the trees change color and people are still enjoying the hours of golden daylight.

Price and Availability in Old Saybrook

Most expensive
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The cheapest day to stay at a vacation rental in Old Saybrook tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Old Saybrook tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Old Saybrook is in March, while the cheapest month is in October. The most popular time to book a vacation rental in Old Saybrook is in the high season in July. Old Saybrook has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Old Saybrook

Rainy days
91 º48
4
81 º32
2
70 º10
4
63 º18
2
59 º-2
2
68 º9
3
63 º19
3
75 º27
2
90 º41
1
90 º48
1
99 º55
1
95 º55
2
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Old Saybrook. The hottest month in Old Saybrook is June, when temperatures peak at 99 ˚F. The coolest month is December, when temperatures drop to -2 ˚F. The wettest month in Old Saybrook is April with 4.07 inches of rain, while the driest month is July with 0.74 inches of rain.

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