House vacation rentals in Old Saybrook

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Quick stats about house rentals in Old Saybrook

  • Total vacation rentals

    Explore 90 vacation rentals in Old Saybrook

  • Nightly prices starting at

    Old Saybrook vacation rentals start at G$20,918 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,580 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Old Saybrook vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Old Saybrook rentals

  • 4.9 Average rating

    Old Saybrook stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated house rentals in Old Saybrook

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.
Home in Niantic
4.97 out of 5 average rating, 223 reviews

Beachfront Paradise

Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

Top guest favorite
The large two-tiered deck is illuminated with soft lighting, creating a cozy atmosphere. A staircase leads to the upper level, where seating and decor are visible. An above-ground pool is situated beside the deck, surrounded by greenery and evening skies.
Home in Montville
4.92 out of 5 average rating, 322 reviews

Casino Wine Down House w/Pool, Game Room, Big Deck

Stay at the end of a quiet, cozy, cul-de-sac while minutes from local attractions. Our house is conveniently located near casinos, Mystic, vineyards, Nature's Art Village, Naval Submarine Base, CT College, USCG Academy and several beaches. Enjoy the fire pit on our large deck under the gazebo year round. In the summer cool off in the pool. In the winter relax and enjoy some cozy time under the stars in the heated igloo. Lot of fun and games! Dogs are family and always welcome at no charge.

Top guest favorite
A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.
Home in Old Saybrook
4.97 out of 5 average rating, 143 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Top guest favorite
A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.
Home in East Haddam
4.93 out of 5 average rating, 339 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Guest favorite
A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.
Home in Westbrook
4.8 out of 5 average rating, 145 reviews

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

Guest favorite
A wooden dock stretches over the calm waters, supported by several sturdy posts featuring black caps. The sky above is clear with soft clouds, enhancing the serene coastal atmosphere.
Home in Old Saybrook
4.92 out of 5 average rating, 104 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

Top guest favorite
An American flag is displayed prominently in the foreground, with the sun setting over the water in the background. The sky is painted with soft hues as the sun begins to dip beneath the horizon, illuminating the shoreline and creating a serene coastal scene.
Home in Old Saybrook
5 out of 5 average rating, 16 reviews

Waterfront Oasis 4Bdr/2b

Direct oceanfront - pure paradise at the beach! Spectacular views of Long Island Sound with a large, partially covered, patio and private steps to the water/sand. Master bedroom with a wall of windows facing the water...wake up each morning to magnificent views. A slider to the waterside patio connects indoor and outdoor living. Dine alfresco, listen to the sound of the waves,watch the sunset - it is truly magnificent as the sun fades into the horizon and the sky illuminates with color.

Top guest favorite
A historic New England home features a classic white exterior with multiple windows. Surrounding greenery includes mature trees and a well-maintained lawn. The side of the house provides a glimpse of a separate structure, enhancing the spacious outdoor area.
Home in Clinton
4.97 out of 5 average rating, 217 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Top guest favorite
Home in Old Saybrook
4.95 out of 5 average rating, 20 reviews

The Saybrook Point Bungalow, Stroll to Downtown

Charming 2-bedroom cottage in Old Saybrook Point neighborhood, just a 1-mile sidewalk stroll to Main Street shops and restaurants. The primary bedroom features a king bed that can convert to two XL twins upon request, plus a second bedroom with a twin. A large couch can sleep a fourth guest. Enjoy warm, modern touches throughout, a Smart TV in the living room, a sunny back porch, and a quiet yard perfect for morning coffee or relaxing after a day exploring this beautiful beach town.

Guest favorite
A two-story waterfront home is set against a serene evening sky, featuring a spacious front lawn. Large windows invite natural light, while a balcony provides an upper-level retreat. A stone patio with seating is visible, enhancing outdoor relaxation options.
Home in Old Saybrook
4.94 out of 5 average rating, 35 reviews

Red Bird Waterfront Home. Dock available extra!

Looking for a stylish and spacious place to stay for your next group trip? Look no further than this waterfront home, perfect for families looking to relax and create lasting memories by the ocean. Interested in hosting an event? Ask us! This beautiful home offers stunning views of the water and plenty of space for your family to enjoy. Whether you're looking to spend your days lounging on the beach, exploring the nearby attractions, or simply relaxing with your loved ones.

Top guest favorite
Home in Old Saybrook
5 out of 5 average rating, 99 reviews

Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace

Explore our Old Saybrook retreat on Great Hammock Rd, a cozy spot near the beach. Perfect for romance or family fun, it boasts stunning views and amenities. Relax in the hot tub, use bikes for local exploration, and enjoy evenings by the fire pit. Indoors, a fireplace adds warmth. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook! Please note Our property is strictly an animal-free zone due to severe allergies persisting in the family.

Top guest favorite
Home in Clinton
5 out of 5 average rating, 19 reviews

The Connecticut Cottage | Historic Modern Charm

Welcome to The Connecticut Cottage — a beautifully restored 1790s stone cottage blending historic New England charm with modern comfort. Thoughtfully renovated from top to bottom, this one-of-a-kind home offers the perfect mix of cozy escape and central convenience along the Connecticut shoreline. Whether you're planning a laid-back coastal getaway or exploring some of New England’s most iconic destinations, you’re perfectly positioned!!

Popular amenities for Old Saybrook house rentals

When is the best time to visit Old Saybrook?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$66,518 GYDG$58,569 GYDG$64,426 GYDG$63,380 GYDG$71,538 GYDG$82,624 GYDG$82,624 GYDG$82,624 GYDG$73,002 GYDG$67,982 GYDG$62,544 GYDG$62,753 GYD
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