House holiday rentals in Old Saybrook

5 out of 5 average rating, 25 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

4.99 out of 5 average rating, 136 reviews

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

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!

4.96 out of 5 average rating, 134 reviews

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

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

4.94 out of 5 average rating, 213 reviews

A spacious deck overlooks calm waters, with a view of boats and distant shoreline. The wooden surface provides ample space for relaxation, while white railings frame the serene scene. Soft clouds drift across the sky, reflecting in the water's surface.

Home in Groton

True Ocean Front Vacationing - Groton/Mystic

Bright and airy contemporary beach house with breathtaking views of Long Island Sound. Conveniently located just 15 mins to Mystic/Stonington; 23 to Foxwoods/Mohegan Sun . Relax on the lower deck and drop a fishing line in the ocean as it greets the seawall at high tide. Or retreat to a private roof deck to enjoy your favorite beverage as you take in the most romantic time of the day, the golden hour featuring beautiful sunsets. Parking for 3-4 cars. We hope you enjoy this escape by the sea!

4.93 out of 5 average rating, 294 reviews

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

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.

4.93 out of 5 average rating, 100 reviews

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 Saybrook Manor

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.

4.97 out of 5 average rating, 209 reviews

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

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.

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.

5 out of 5 average rating, 15 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.

5 out of 5 average rating, 205 reviews

An open-concept living space is illuminated by natural light, featuring a modern kitchen with a large marble island and bar seating. A cozy seating area is positioned nearby, with a view of a decorative sign reading 'Relax.' A spiral staircase leads to the upper loft.

Home in Preston

Lake Home w/Game Room 5 Min To Foxwoods & Mohegan

Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 5 min. from Foxwoods, 10 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

4.97 out of 5 average rating, 210 reviews

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

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.

A modern kitchen is highlighted by white cabinetry and marble countertops, featuring high-end stainless-steel appliances. An adjacent dining area with a wooden table and chairs is visible in the background, providing a spacious and inviting layout.

4.95 out of 5 average rating, 61 reviews

Water Views and Walk to Beach

This house is perfect for families or groups that want to enjoy beautiful Old Saybrook in a spacious, newly remodeled, three-story home in a quiet neighborhood close to the beach. Gleaming hardwood floors and stunning kitchen with a farmhouse sink, and high end appliances. The kitchen is immaculately appointed with top-of-the line appliances and everything you need to cook a gourmet meal. Large deck and an outside shower are included. Water view from the master bedroom martini deck.

4.95 out of 5 average rating, 751 reviews

A serene view of the Poquetanuck Bay is captured at dawn, showcasing a calm water surface reflecting pastel hues of pink and purple. Surrounding trees frame the scene, while homes on the opposite shore are silhouetted against the soft morning light.

Home in Preston

Entire House Magical Waterfront Getaway

4 MINUTES TO MOHEGAN SUN! Yet quiet and secluded! Waterfront home! Come relax in this well appointed home with breathtaking view of the Poquetanuck Bay! Enjoying the absolutely gorgeous view from the balcony or porch! Or simply relax, sit around, enjoy each other’s company! Smart TV grants you easy access to thousands of streaming apps! 25 minutes to Ocean Beach, Mystic seaport, Mystic aquariums, Submarine and Library Museum in Groton! 15 minutes away from Foxwood casino!

Popular amenities for house rentals in Old Saybrook

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 106 reviews

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

Home in Montauk

3 BR/Pool. Walk to Beach & Town!

4.97 out of 5 average rating, 212 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

4.91 out of 5 average rating, 112 reviews

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

Breathtaking home with unforgettable views & pool!

4.92 out of 5 average rating, 127 reviews

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

Home in Springs

Private & Pristine with Pool and Kid’s Playard

4.91 out of 5 average rating, 118 reviews

Home in Springs

Serene + Chic* 1 block to water *8 mins to Main St

4.9 out of 5 average rating, 219 reviews

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

4.97 out of 5 average rating, 184 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

4.92 out of 5 average rating, 117 reviews

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 Mattituck

Modern farmhouse w/ pool, beach, horses and winery

Weekly house rentals

4.97 out of 5 average rating, 77 reviews

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Indian Neck

Adorable Beach House on LI Sound

A cozy living area features a brown sofa with decorative pillows and a neutral-toned ottoman. A round green pouf adds a pop of color. Natural light enters through large windows adorned with sheer curtains. A small dining table is situated nearby with two chairs, enhancing the inviting atmosphere.

5 out of 5 average rating, 11 reviews

Plant Lovers Paradise

4.98 out of 5 average rating, 48 reviews

An aerial view captures the expansive sandy beach stretching along the coastline, adjacent to serene waters reflecting sunlight. Houses line the shore, with some beach chairs positioned near the water's edge, creating a peaceful coastal scene.

Home in Westbrook

Barnacle Bay Beach House

5 out of 5 average rating, 16 reviews

A bright living room features large windows that overlook a serene view of the pond. Comfortable gray sofas and two navy blue chairs with yellow accents are arranged around a glass coffee table on a patterned area rug. A stone fireplace adds a cozy touch to the space.

Home in Essex

4 Bedrooms Modern Home with Water View & Access

A converted granite mill is surrounded by verdant lawns and trees. The two-story building features numerous windows, reflecting natural light. A paved path leads to a covered seating area nearby, complementing the tranquil outdoor setting.

5 out of 5 average rating, 17 reviews

Relax and Refresh at the Mill-on-Sill

The farmhouse features a light yellow exterior with white shutters, complemented by a large green lawn. A spacious porch provides access to the front door, and a tall tree adds shade. The building's gabled roof and large windows create a welcoming appearance.

4.94 out of 5 average rating, 16 reviews

Old Lyme Farmhouse

4.99 out of 5 average rating, 67 reviews

Home in Saybrook Manor

3BR Updated Cottage w/ Pool in Old Saybrook

5 out of 5 average rating, 29 reviews

The sunken living room showcases expansive windows offering unobstructed views of the water, allowing natural light to fill the space. A spacious gray couch faces a low black table, while a comfortable reading chair with an ottoman is positioned nearby, creating an inviting gathering area.

Home in Guilford

3BR Waterfront Oasis on Joshua Cove, Private Beach

Private house rentals

4.96 out of 5 average rating, 28 reviews

A wooden dining set is positioned on a deck overlooking the water, featuring a large red umbrella providing shade. Tables are set with blue plates, and greenery frames the peaceful view of the inlet and distant seating by the shore.

Home in Southold

North Fork Waterfront Escape · Sunset Views

An aerial view of a spacious home with a light-colored exterior is displayed, surrounded by scenic natural landscapes. Large windows enhance the modern design, and the Connecticut River is visible in the background, reflecting the clear blue sky.

4.83 out of 5 average rating, 58 reviews

Stunning house on CT river !

4.87 out of 5 average rating, 46 reviews

A charming two-story house is set on a green lawn, featuring white siding and dark green shutters. Gravel pathways lead to the entrance, and a small shed is visible to the side. Mature trees provide shade, enhancing the peaceful outdoor setting.

Home in Madison

Cozy beach cottage close to everthing

4.93 out of 5 average rating, 29 reviews

An inviting library is highlighted by built-in bookshelves filled with various books and decorative items. A comfortable armchair and a small round table sit on an ornate rug, while a lamp provides soft illumination. A mural depicting a serene landscape is painted on the wall.

Home in Lyme

Tinker Gardens

A two-story beach home is presented, featuring white siding and black shutters. The front steps lead to a centrally located entrance. A well-manicured lawn and gravel driveway surround the property, providing access to the garage on the left side.

5 out of 5 average rating, 10 reviews

Fully Remodeled w/ Beach Access in Old Lyme!

5 out of 5 average rating, 16 reviews

An aerial view of Quarry House showcases its Mid-Century Modern design surrounded by lush trees. The expansive wraparound deck with seating provides a space for relaxation, while the home's large windows reflect the evening light, seamlessly blending indoor and outdoor living.

Home in Haddam

Quarry House: Mid-Century Modern

5 out of 5 average rating, 29 reviews

A scenic waterfront terrace is framed by natural rock formations and lush greenery. An umbrella provides shade over a seating area featuring two Adirondack chairs and a small table, all offering unobstructed views of the water and boats in the distance.

Home in Guilford

Mulberry Seaside Cottage