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Holiday houses in Old Saybrook

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Top-rated holiday rentals in Old Saybrook

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

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Top Guest favourite
Home in Old Saybrook
5 out of 5 average rating, 32 reviews

Sunrise Beach Cottage

Our newly renovated home is steps away from Cornfield Point’s many private Beaches, tennis court, boardwalk and Sandbar. With Multiple Water views, 4 private beaches, new appliances, grill, furniture, washer dryer, beds, patio, fire pit, golf, kayaking, pickle ball , tennis, playground, clubhouse, The Kate , Casino’s , 3 lighthouses, private boat ramp. We will try to accommodate your dog too. Sat - Sat 7 night stays, other by request. Sunrises, Sunsets & Sea Breezes Academic Renters 2025

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Top Guest favourite
A cozy living area features a brown sofa facing a wall-mounted flat-screen TV. A small desk with a chair is positioned next to a window, adorned with patterned curtains. A blue accent chair complements the space, and a striped area rug adds warmth to the hardwood floor.
Cottage in Old Saybrook
4.97 out of 5 average rating, 35 reviews

Serene Coastal Cottage steps from South Cove

Welcome to your perfect private seaside escape! Nestled in the heart of Old Saybrook, this cozy 1-bedroom cottage blends classic New England charm with modern comfort. Just a short stroll from the beach and historic downtown, this cottage is ideal for a relaxing getaway or a romantic retreat. Wake up to salty sea breezes and enjoy your morning coffee on the deck. Whether you're exploring the nearby attractions, dining at local restaurants, or unwinding with a book, you’ll feel right at home.

LocationFamilyBathroom

Guest favourite
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.

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Guest favourite
Apartment in Essex
5 out of 5 average rating, 14 reviews

Quintessential Essex. Steps from the Steam Train!

Enjoy a stylish experience at this centrally-located apartment. This 2 bedroom unit boasts plank flooring and tons of natural light! Kitchen has stainless appliances, granite countertops and subway tile backsplash. Large living room with many windows, tiled shower with modern vanity, spacious bedrooms and gorgeous sunroom overlooking the Essex Steam Train! Short walk to Sayulitas and the Cheese Shop of Centerbrook. Short ride to Essex Village, the Ivoryton Playhouse, and the CT Shoreline!

LocationFamilyCheck-in

Top Guest favourite
A welcoming view of Belle Vue Cottage features a well-kept lawn with a sign indicating its name. The cottage is framed by trees, with a driveway leading to it. A garage is visible in the background, contributing to the serene atmosphere of the neighborhood.
Cottage in Old Saybrook
4.99 out of 5 average rating, 157 reviews

Beautiful View Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

ValueFamilySleep quality

Superhost
A charming home exterior is lined with vibrant green ivy, surrounded by a lush garden area. A gravel pathway leads to the entrance, and cozy seating arrangements are visible in front of the house. Large windows allow natural light to fill the interior.
Cottage in Old Saybrook
4.78 out of 5 average rating, 106 reviews

Storybook 2 Bedroom Cottage

Enjoy a relaxing stay at this charming storybook home which has just been refreshed professionally and redesigned with unique and gorgeous antique furnishings and decor. Built in 1895, the home was re-envisioned by designer Charles Spada in the 90’s. A lovely private back yard with beautiful stone work and plantings. The proximity to shopping, galleries, restaurants and Old Saybrook, Town Beach and Katherine Hepburn theater makes this location ideal.

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Top Guest favourite
A charming entrance is framed by an archway adorned with decorative ironwork. The door, painted in a soft turquoise, is complemented by a welcoming wreath. Lush green foliage surrounds the entryway, creating a serene outdoor environment.
Cottage in Old Saybrook
4.74 out of 5 average rating, 248 reviews

The Cottage

Step into a piece of history with this charming, fully converted 1930s changing house. Ideally located, it’s just a short stroll to downtown or a scenic bike ride to the beach, putting the best of the area right at your doorstep. Inside, you’ll discover a thoughtfully designed studio layout, offering the perfect setting for a peaceful getaway. The Cottage seamlessly blends comfort, convenience, and character, creating a truly inviting retreat.

ValueFamilyDecor

Guest favourite
The exterior of the cottage is characterized by distinctive brown shingles, complemented by a bright blue sky overhead. Windows are symmetrically arranged, while a decorative sun emblem adds visual interest. An American flag waves near the apex, and a pumpkin is placed near the entrance.
Cottage in Old Saybrook
4.91 out of 5 average rating, 56 reviews

Luxury Driftwood Cottage @ Saybrook Point

The Driftwood Cottage is your next seaside getaway, with two King beds and a full and just steps away from the Saybrook Point Marina nestled between the Long Island Sound and Connecticut River. Whether you are docking for the weekend, attending a wedding, or need a romantic getaway. Enjoy the warmth and history of Historic Old Saybrook with our cozy cottage as home base. We love Connecticut and making ever-lasting memories for our guests!

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Top Guest favourite
The exterior of the historic barn is featured, showcasing weathered wood siding and a welcoming entrance with double doors. The structure is surrounded by trees and a gravel pathway leading to the front door. Soft morning light highlights the natural beauty of the setting.
Barn in Essex
4.96 out of 5 average rating, 187 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

LocationValueBarbecue

Top Guest favourite
A living area features a comfortable sectional sofa adorned with decorative pillows. Two light blue armchairs are positioned beside a small table with a patterned top, while a television stand and a floor lamp complete the inviting space. Sunlight is visible through a window.
Home in Old Saybrook
4.92 out of 5 average rating, 109 reviews

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

FamilyValueWalkability

Top Guest favourite
A well-lit suite features a spacious bed with purple and white accents. A kitchenette with white cabinetry includes a refrigerator and sink. A wall-mounted television displays scenic imagery. Soft lighting highlights the plants arranged on shelves, creating a calming environment.
Home in Old Saybrook
4.98 out of 5 average rating, 58 reviews

The Channelside

The Channelside suite is a one bedroom suite with a queen bed, couch, and upon request a twin bed can be set up if needed. Walking distance to Marinas, a great restaurant and 2 bars. Fishing and boat launch are just around the corner, room to park your small boat and truck. It has a separate keyless entrance from the main home. 5 minutes to shopping and great restaurants, close to beaches and area attractions.

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Guest favourite
Tiny home in East Lyme
4.99 out of 5 average rating, 150 reviews

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

LocationValueKitchen

Popular amenities for Old Saybrook holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Old Saybrook's top sights

Florence Griswold Museum

86 locals recommend

Essex Steam Train & Riverboat

165 locals recommend

Connecticut River Museum

67 locals recommend

Other great holiday rentals in Old Saybrook

Superhost
Cottage in Old Saybrook
4.74 out of 5 average rating, 89 reviews

- The Cottage-Voted Number one in town by AB&b

ValueLocationComfort

Guest favourite
A cozy living area is furnished with a beige sofa, a round wooden coffee table, and stylish light blue armchairs. A large window allows natural light to fill the space. Potted plants add a touch of greenery, creating a relaxed atmosphere.
Condo in Old Saybrook
4.92 out of 5 average rating, 100 reviews

Seashore getaway - CT shoreline

ValueLocationGetting around

Top Guest favourite
Apartment in Chester
4.96 out of 5 average rating, 57 reviews

The Little Chestnut.

LocationValueDecor

Top Guest favourite
Cottage in Old Saybrook
5 out of 5 average rating, 8 reviews

Osprey Cozy Cottage | Near Downtown & Beaches

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Guest favourite
Home in Old Saybrook
5 out of 5 average rating, 12 reviews

The Saybrook Point Bungalow, Stroll to Downtown

FamilyLocationAmenities

Top Guest favourite
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

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Top Guest favourite
Home in Deep River
4.97 out of 5 average rating, 37 reviews

Private Barn Retreat Nestled In Nature

LocationNearbyDecor

Top Guest favourite
Home in Old Saybrook
5 out of 5 average rating, 95 reviews

Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace

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When is the best time to visit Old Saybrook?

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Frequently Asked Questions

  • What are the best places to stay in Old Saybrook?

    Old Saybrook has accommodations near the shoreline, around Main Street, and just outside the Connecticut River. Areas near the beach and the town center help guests explore local shops, dining, and water activities.

  • What are the best things to do in Old Saybrook with kids?

    Families often explore sandy beaches, playgrounds, and nature centers around Old Saybrook. The town has an ice cream shop, waterfront parks, and easy trails that are great for younger travelers.

  • What are some of the best things to do in Old Saybrook?

    Old Saybrook has sandy beaches, peaceful marshes for exploring by kayak, and a lively Main Street with local shops and galleries. The town also has historic sites and a theater for those interested in arts and culture.

  • How is the weather in Old Saybrook?

    Old Saybrook has cold winters near 24–38°F (-4–4°C), with possibilities of snow, and warm summers that reach 68–83°F (20–29°C). Rain falls throughout the year, so a waterproof layer is useful for all seasons.

  • When is the best time to visit Old Saybrook?

    Late spring through early fall is often recommended for visiting Old Saybrook, with warmer afternoons near 60-83°F (15-29°C), blooming landscapes, and outdoor events. Colder months have a quieter atmosphere for those seeking a slower pace.

  • What are the best places to visit in Old Saybrook?

    Visiting the Katharine Hepburn Cultural Arts Center, the Lynde Point Lighthouse, and Main Street’s shops are often recommended in Old Saybrook. Local nature parks invite exploration year-round.

  • What are some hiking trails in Old Saybrook?

    Explore the Fort Saybrook Monument Park for a short historical stroll or the trails at The Preserve for woodland walks. Local marsh paths are great for spotting birds and quiet reflection.

  • What are some family activities we can do in Old Saybrook?

    Old Saybrook has family-friendly mini golf, interactive art workshops, and public parks for picnics or kite flying. Kids often enjoy exploring tidal pools or taking boat rides on the nearby river.

  • What are some of the best day trip ideas from Old Saybrook?

    Explore nearby coastal villages, nature reserves, or historic lighthouses for a change of scenery. Many explore local vineyards or visit neighboring small towns known for museums and maritime history.

  • Are there any pet friendly accommodations available in Old Saybrook?

    Many stays in Old Saybrook welcome pets, especially near the beach and in residential neighborhoods. Filter options when searching to find spaces with pet-friendly amenities.

  • What are some local tips for visiting Old Saybrook?

    Locals suggest packing in layers to adjust for changing weather and exploring beyond Main Street for shops, marsh walks, and cozy cafes. Consider bringing a bike or renting a kayak for a new perspective on the inlets and coastal scenery.

  • What is Old Saybrook known for?

    Old Saybrook is known for its maritime history, sandy beaches, and small-town New England charm. The town’s connection to Katharine Hepburn and its classic Main Street culture are often highlighted.

  • What are the best hidden gems to explore in Old Saybrook?

    Old Saybrook has quiet marsh trails, lesser-known art galleries, and historic cemeteries that reflect centuries of local stories. Small waterfront parks and tucked-away bookshops are often suggested for a peaceful break.

  • What are the best foods to try in Old Saybrook?

    Seafood is frequently suggested—look for dishes featuring fresh clams, lobster rolls, or locally caught fish. Old Saybrook also has bakeries known for pies and seasonal local produce.

  • What should I bring for a trip to Old Saybrook?

    Pack layers for changing weather, comfortable shoes for exploring marshes or Main Street, and a hat for sun protection in summer. A rain jacket can be useful, especially in spring or fall.

  • What is the nightlife in Old Saybrook like?

    Old Saybrook has a laid-back nightlife scene, with casual pubs, wine bars, and some spots featuring live music. Some evenings include community performances or small theater shows around Main Street.

  • What are the most popular events or festivals in Old Saybrook?

    Seasonal festivals with art, music, and food pop up around Main Street in the summer and early fall. Holiday parades, craft fairs, and outdoor concerts are frequently suggested community gatherings.

  • Are there family friendly vacation rentals in Old Saybrook?

    Many vacation rentals around Old Saybrook are family friendly, with extra bedrooms, outdoor spaces, and proximity to beaches or playgrounds. Listings often include amenities like full kitchens and laundry.

Quick stats about holiday rentals in Old Saybrook

  • Total holiday rentals

    Explore 130 holiday rentals in Old Saybrook

  • Nightly prices starting at

    Old Saybrook holiday rentals start at $100 AUD per night before taxes and fees

  • Verified guest reviews

    Over 4,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Old Saybrook holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Old Saybrook rentals

  • 4.9 Average rating

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

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