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Vacation Rentals in Old Saybrook, Connecticut

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about Old Saybrook

Old Saybrook, Connecticut Vacation Rentals and Tourism

As one of the oldest towns in Connecticut, Old Saybrook is a popular spot for history buffs to visit; the Fort Saybrook Monument Park and the General William Hart House are both must-see attractions. But does anything beat the view from an Old Saybrook beach house? Old Saybrook vacation rentals give history lovers and beach bums, and history-loving beach bums, a chance to take in the natural scenery and interesting attractions of the town, in peace and quiet.

Maybe you can’t wait to take a ride on the scenic Old Saybrook Trolley, or maybe you’re looking forward to lazy mornings spent reading a book on the porch of your Old Saybrook waterfront condo; whatever the case, now is the best time to book your Connecticut accommodations.

Old Saybrook sits at the mouth of the Connecticut River, and is located near two beautiful coves. Therefore Old Saybrook cottages and homes feature some of the loveliest views in all of New England. Whether you’re hanging out at the marina, playing a round of mini-golf at Saybrook Point, or visiting the colonial sites, your time spent in an Old Saybrook beach house or condo will be aesthetically pleasing, easygoing, and leave a long-lasting impression.

The key to finding your dream Old Saybrook waterfront condo is to first think about the particular needs of you and your party, and of course your budget. No doubt, one of the Old Saybrook vacation rentals found here will fit in well with your vacation plans.

So consider these picturesque Old Saybrook cottages, homes, and condos, before getting ripped off with a hotel room. Chances are you’ll find it hard to ever make a hotel reservation again!

Sites and tours to see

Fort Saybrook Monument Park
General William Hart House
Old Saybrook Trolley
Saybrook Point

Old Saybrook Vacation Rental Deals

Old Saybrook has so much to offer it’s no wonder that thousands of visitors come here every year. Stay in one of our low-cost Old Saybrook vacation rentals and find out why so many people love to visit Connecticut. And you can save money on your trip with our discounted rates and Old Saybrook last minute deals. With so many deals you are sure to get the best value for your money. Come and see the great and affordable Old Saybrook accommodations that we have in this area. You will love your trip here because of the large amounts of fun with cheap prices. Book a discounted Old Saybrook vacation home today.

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Old Saybrook things to do


Florence Griswold Museum

Big news at Cafe Flo this year: they've decamped from the Landscape Center Barn to the long swath of terrace smack on the banks of the Lieutenant more


Connecticut River Museum

This is a small gem of a museum located in the former steamboat wharf building at the end of the road in Essex. Exhibits highlight the CT river and more


Rocky Neck State Park

The beach I've been going to my whole life and will always come back to. Admission is $9 for state residents, parking is plentiful and it is a great more


Sea Sprite Sport Fishing

Highly recommended! I went on the Sea Sprite with friends today that have been fishing with Captain Pete for over twenty years. They go twice a year, more


Cross Sound Ferry

I live in Boston but travel on Long Island for work purposes. Sometimes it's a pain in the ass to travel by car from the most Eastern parts of the Island, more


Orient Beach State Park

For what this is, this is a phenomenal beach. And what it is: a quiet pristine beach that family friendly and has beautiful scenery. We enjoyed an more


Goodspeed Opera House

This is an amazing historical theatre that performs very high quality productions. As others have said, it's small and I doubt a bad seat in the house. more


Katharine Hepburn Cultural Arts Center

Beautiful tribute to Katharine Hepburn. This center offers a variety of performances and events. The lower level has a small museum of Hepburn more


The Nut Museum

There will never be another The nut museum is no more but I am going to review it posthumously. It was such a fiercely unique and creative place that more


Ivoryton Playhouse

Great little local theater!! We saw Footloose on 7/6 and the actors and musicians were wonderful. We were able to get decent seats the morning of more


Brewer's Dauntless Shipyard

The absolute best marina out there. Amazing views. Tip top service. Excellent to visit by boat as you can just walk to townread more


Indian River Marina and Kayak Rentals

Outstanding service from a very knowledgeable staff and after some initial "refresher" tips I was in my way! Awesome location to explore the Clinton more


Kontokosta Winery

The place is popular. The staffs look super busy, jumping from one group to another. The wine is good, but nothing to die for. I come here for one more


Marquee Cinemas 12

Nice location and always a good selection of films. Friendly staff. And I'm happy with the ticket prices. (Crazy expensive but better than more



We usually practice in Manhattan but spend summers in Westbrook so we thought we would try Pradipika as they moved into a new space. Beautiful, clean more

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Beach Front Rental
Old Saybrook House Rental Picture
  • bedrooms 3
  • community Cornfield Point
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $1,000 - $3,000 /wk

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NEW PRICE Waterview 80 Feet to Wide Open Sandy Beach
Old Saybrook Condo Rental Picture
  • bedrooms 3
  • community Indian Town
  • rental type Condo
  • sleeps 8
  • baths
  • rates (USD) $1,500 - $1,800 /wk
    $5,500 - $6,000 /mth

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Chalker Beach - 4 Kenn Road
Old Saybrook House Rental Picture
  • bedrooms 3
  • community Chalker Beach
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 - $1,600 /wk

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Hartlands Castle/The Castle Inn
Old Saybrook House Rental Picture
  • bedrooms 4
  • community Cornfield Point
  • rental type House
  • sleeps 12
  • baths 5
  • rates (USD) $5,000 - $6,000 /wk
    $20,000 - $24,000 /mth

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Saybrook Point Inn and Spa
Old Saybrook House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,599 - $2,999 /wk

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Wonderful location, walk to beach, private yard, pets ok, credit cards
Old Saybrook Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $175 - $280 /nt
    $1,200 - $1,900 /wk
    $4,800 - $7,500 /mth

47 reviews write a review

**Charming**New England Historical Ppty Ideal for Weddings&Large Groups w/garden
Old Saybrook House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths 2
  • rates (USD) $250 - $1,200 /nt
    $1,600 - $3,900 /wk
    $7,000 - $12,000 /mth

46 reviews write a review