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House holiday rentals in Old Saybrook

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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 favourite
A charming cottage is depicted with a shingle exterior, a welcoming front porch, and a chimney. The grassy landscape is flanked by flowering shrubs, and a path leads to the entrance. A red barn is visible in the background, enhancing the rural setting.
Home in Waterford
4.98 out of 5 average rating, 132 reviews

Niantic River Beach Cottage | Waterviews

Kick back and relax in this quiet, stylish New England beach cottage with water views, a private neighborhood beach, an outdoor shower, and a sunny patio for coffee or evening wine. Just minutes from downtown Niantic, you’ll find beaches, cafés, bakeries, ice-cream stands, seafood, boutiques, boat launches, trails, outdoor concerts, and more—all within a short drive or bike ride. Perfect for a romantic getaway, a family weekend, or some quiet coastal downtime. See why guests love staying here!

Top Guest favourite
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 Saybrook Manor
4.96 out of 5 average rating, 134 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

Guest favourite
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, 278 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 favourite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in North Fork
4.92 out of 5 average rating, 112 reviews

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Top Guest favourite
A serene view of a quiet street leading to the water, framed by trees. Visible are parked vehicles along the roadside, with the sparkling bay in the background, indicating proximity to the beach. A basketball hoop stands on the right side, contributing to the residential atmosphere.
Home in East Lyme
4.98 out of 5 average rating, 160 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Top Guest favourite
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, 206 reviews

Beachfront Paradise

Beautiful beachfront home available weekly in season (6/20/26-9/5/26) 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, movie theatre, 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.

Guest favourite
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, 210 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.

Guest favourite
A wide view of a sandy beachfront stretches along the coastline, bordered by calm blue waters under a clear sky. Lush greenery can be seen in the distance, suggesting a nearby park or recreation area. Several individuals are spaced along the shore enjoying the beach.
Home in Waterford
4.93 out of 5 average rating, 122 reviews

Salty Breeze - Waterfront Cottage on the Cove

Enjoy your stay in this peaceful waterfront cottage. After the day relax on the 3 season screened- in porch or climate controlled sunroom watching the winter waterfowl on the wintery cove or relax in the backyard next to the fire pit with hot coco. Walking distance to Ocean Beach Park, Waterford Town Beach. Within 30 minutes of Niantic, downtown Mystic, Ferry's to Block, Fisher's and Long Islands, by museums, the Nautilus, Mohegan and Foxwoods Casinos, tons of great restaurants

Guest favourite
A spacious living room is highlighted by a unique whale wall art piece and a cozy seating arrangement. A comfortable gray sofa is paired with a nautical-themed chair. Large windows allow natural light to fill the room, creating a welcoming atmosphere.
Home in New London
4.87 out of 5 average rating, 157 reviews

Beauty and the Beach!

Welcome to Beauty and the Beach, where you can come and relax with the whole family or come alone to get away from the busynesses of life! The property is located within an 8 minute walk to Ocean Beach Park and a block away from Alwife cove. With all year recreation. we are located within a short distance to: - Coast Guard Academy -Navy Sub Base -Mohegan Sun -Historic Mystic -Shopping and Great Dining Experiences! -Scenic hiking trails Come and embrace the New England Salty Life!

Top Guest favourite
An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.
Home in Haddam
4.99 out of 5 average rating, 144 reviews

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Guest favourite
A cozy living area features a brown sectional sofa adorned with patterned throw pillows. A black coffee table sits on a striped area rug, providing a neutral contrast to the light hardwood flooring. Natural light filters through multiple windows, enhancing the welcoming ambiance.
Home in North Fork
4.93 out of 5 average rating, 213 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Top Guest favourite
A charming single-level home features a covered front porch supported by sturdy columns. The exterior is complemented by a combination of stone and siding, surrounded by a well-maintained lawn and trees providing shade. A pathway leads to the porch entrance.
Home in Waterford
4.91 out of 5 average rating, 199 reviews

Shore Drive - 2 Bedroom/2 Bath/Bunk/Queen Oasis

Stay with us for a relaxing, family beach experience! This is a newly remodeled (2022) home with a spacious patio, seating w/table for 6 and large backyard. Walking distance to Waterford & Ocean Beach, Waterford Beach Park, Eugene O'Neill Theater and Harkness State Park. 15-20 min drive to Mystic, Stonington, Vineyards, 25 min to Mohegan Sun & Foxwoods. Close to the Lawrence + Memorial Hospital, Pfizer, GD (EB), CT College, Mitchell, USCGA US Navy Base Groton.

Popular amenities for Old Saybrook house rentals

When is the best time to visit Old Saybrook?

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Avg. price$501 NZD$472 NZD$486 NZD$504 NZD$569 NZD$657 NZD$657 NZD$657 NZD$581 NZD$541 NZD$497 NZD$499 NZD
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Quick stats about house rentals in Old Saybrook

  • Total holiday rentals

    Explore 90 holiday rentals in Old Saybrook

  • Nightly prices starting at

    Old Saybrook holiday rentals start at $166 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Old Saybrook holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Old Saybrook rentals

  • 4.9 Average rating

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