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Old Saybrook Vacation Rentals

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Our Favorite Vacation Rentals in Old Saybrook

  • Oceanfront, Private Beach
     Country House
    Booking.com
    From
    $1,450
  • Marina Point Villas at Saybrook Point
     2br Country House
    HolidayLettings
    From
    $1,532
  • Stunning Artisan Waterfall Escape [Walk to Downtown]
     Country House
    Booking.com
    From
    $330
  • NEW! Saybrook Manor House, Walk to Cove Beach!
     3br Home/Apartment
    HolidayLettings
    From
    $479
  • The Old Sindelar Farm
     1-star Farm Stay
    Booking.com
    From
    $130
  • Luxurious living on a bucolic alpaca farm
     2br Home/Apartment
    HolidayLettings
    From
    $402
  • Victorian Seasons 5-bedroom Manor
     Country House
    Booking.com
    From
    $1,250
  • Peace Barn in the heart of the CT River Valley
     4br Home/Apartment
    HolidayLettings
    From
    $307
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Check prices for these upcoming dates

Old Saybrook Vacation Rentals with a Pool

  • Large Waterfront House with Pool
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,582
  • Winterwood Country Estate - 26 Scenic Acres
    Excellent3br Home/Apartment
    Airbnb
    From
    $632
  • NOFO Escape
     6br Home/Apartment
    Airbnb
    From
    $1,099
  • Waters Edge Resort and Spa - Oceanfront Villa by the Sea - 1275 sq ft
     2br Home/Apartment
    Airbnb
    From
    $1,092
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Old Saybrook Vacation Rentals with Wi-Fi

  • White House on Oldsaybrook Ct.
    Good3br Home/Apartment
    Airbnb
    From
    $137
  • Newly renovated beach home! First time available
    Excellent3br Home/Apartment
    Airbnb
    From
    $565
  • Great family house
    Good3br Home/Apartment
    Airbnb
    From
    $232
  • SeaStar of Old Saybrook
     3br Home/Apartment
    Airbnb
    From
    $295
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Old Saybrook Pet-Friendly Vacation Rentals

  • Steps to beach 4bd 2 bth Sleeps 14
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $746
  • NEW! Niantic Home w/ Patio+Grill - 2 Mi. to Beach!
     3br Home/Apartment
    HolidayLettings
    From
    $298
  • 3 Room Eco-Friendly Suite in Historic 1790 Home
    Excellent3br Home/Apartment
    Airbnb
    From
    $364
  • Unique apartment, former contemporary art gallery.
    Excellent2br Home/Apartment
    Airbnb
    From
    $158
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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.

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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.
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The Weather in Old Saybrook

Rainy days
70° 10°
4
63° 18°
2
59° -2°
2
68° 9°
3
63° 19°
3
75° 27°
2
90° 41°
1
90° 48°
1
99° 55°
1
95° 55°
2
91° 48°
4
81° 32°
2
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Old Saybrook. The warmest months in Old Saybrook are June and May, when temperatures reach 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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What Expert Travelers Think

  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
    Visit Coco Travels

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
    Visit Amanda Alston

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
    Middle Class Dad

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