House vacation rentals in Old Saybrook

4.99 out of 5 average rating, 176 reviews

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

Home in Vernon

Luxe Bolton Lake

Stay at Luxe Bolton Lake and feel like you are a million miles from home! The Luxe features a beautiful waterfront, 3 bedrooms/3 full bathrooms and a year-round outdoor jacuzzi. Also included: gorgeous primary bedroom suite, artistic furnishings, cozy fireplace, coffee bar, complimentary snacks, speedy WiFi, large deck, fire pit, kayaks, board games, and much more. The Luxe is perfectly suited for families and guests of all ages, so come stay at Luxe and make memories that will last a lifetime!

4.97 out of 5 average rating, 220 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 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.

4.95 out of 5 average rating, 768 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 3 bedrooms 2 baths 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!

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.

4.96 out of 5 average rating, 138 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

4.85 out of 5 average rating, 146 reviews

Home in Hampton Bays

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

4.93 out of 5 average rating, 326 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.

4.96 out of 5 average rating, 217 reviews

A serene garden space features lush green foliage and vibrant pink flowers, with a rustic wooden chair positioned to overlook a gentle waterfall. The surrounding trees provide a natural canopy, creating a peaceful atmosphere for relaxation.

Home in Chester

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

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.

4.92 out of 5 average rating, 103 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.

4.94 out of 5 average rating, 154 reviews

A spacious home is visible against a twilight sky, featuring an outdoor fire pit surrounded by Adirondack chairs. Soft illumination from the deck outlines the structure, while trees provide a natural backdrop. Path lights create a welcoming atmosphere in the extensive yard.

Home in Waterford

Niantic Bay & Play House-Game room, mins to beach

Stay at the end of a quiet cul-de-sac located half a mile from downtown Niantic with several beaches located minutes from the house. The Niantic Bay & Play House is packed full of indoor and outdoor games while conveniently located close to several attractions. Sit by the fire pit, play Corn Hole or Frisbee Golf in our large open private backyard. Inside you will find big open spaces to relax with friends and family. Our house is perfect for everyone including your furry family member.

4.98 out of 5 average rating, 173 reviews

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

4.99 out of 5 average rating, 105 reviews

A two-story home with white siding and green shutters is depicted. The front porch features a welcoming railing and an American flag is visible. A driveway leads to a garage with a manual door, and grassy areas are present on the property.

Home in Niantic

The Beach House (Costa Casa Pelo Mar)

NEWLY RELISTED AT A GREAT VALUE! Amazing amenities and beach location. Family friendly home in a private beach community, in Niantic, CT. Parking pass included, to walk/park steps away from our private beach & walk into Rocky Neck State Park. A short drive to downtown Niantic, great restaurants, Foxwoods & Mohegan Casinos, Shopping (Niantic, Westbrook Outlets, Clinton Crossing), Mystic Aquarium and Seaport, Garde Arts Center, The Kate & SE CT Children's Museum

4.93 out of 5 average rating, 136 reviews

Home in Clinton

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: June 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Popular amenities for Old Saybrook house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 116 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, 214 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

4.9 out of 5 average rating, 115 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!

4.99 out of 5 average rating, 138 reviews

Home in Stonington

FREE Private Indoor Heated Pool - Mystic Home

4.96 out of 5 average rating, 109 reviews

Home in North Fork

Stunning Farmhouse in NoFo I Heated Pool, Wineries

4.99 out of 5 average rating, 177 reviews

Home in Commack

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

4.91 out of 5 average rating, 236 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, 191 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

Weekly house rentals

A charming duplex features a light blue exterior with white trim and a welcoming front porch. Two Adirondack chairs are positioned on the porch, inviting relaxation. Windows enhance natural light, while neatly trimmed shrubs add greenery to the inviting facade.

4.75 out of 5 average rating, 32 reviews

Adorable Cottage with porch, walk to water & town

4.88 out of 5 average rating, 51 reviews

SeaStar Scenic Marsh View Close Walk To Ocean

4.94 out of 5 average rating, 31 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 sunny wraparound deck is featured with multiple seating options, including four Adirondack chairs and a dining table sheltered by a large umbrella. The surrounding views include coastal greenery and distant houses, highlighted against a clear blue sky.

4.62 out of 5 average rating, 90 reviews

Money Point Beach House- Deck+Views + Beach Access

5 out of 5 average rating, 18 reviews

Home in Guilford

Guilford Field House

5 out of 5 average rating, 37 reviews

A bright living area features large windows that overlook the ocean, allowing natural light to fill the space. The room is furnished with a blue sofa, two armchairs, and a coffee table. A small plant adds a touch of greenery, and a dining area is visible in the background.

Home in Clinton

Soundscape Beachfront House!

4.97 out of 5 average rating, 93 reviews

A white two-story house is featured, with black-shuttered windows and a decorative front porch lantern. An American flag flutters at the front, and a neatly maintained fence surrounds the lawn. A tree without leaves is visible in the background on a clear day.

Home in Essex

Ideal Historic Home in Essex Village

A charming beachfront cottage exterior is depicted, showcasing a gabled roof and grey shingle siding. Large windows allow natural light to fill the interior, while a white table is set on the patio. Green grass surrounds the cottage, enhancing the coastal setting.

4.8 out of 5 average rating, 5 reviews

Addison's Oasis

Private house rentals

4.82 out of 5 average rating, 61 reviews

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.

Home in Old Lyme

Stunning house on CT river !

4.86 out of 5 average rating, 56 reviews

Duckling Crossing | Beach House on the Sand

4.98 out of 5 average rating, 91 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 Branford

Adorable Beach House on LI Sound

A collage showcases the various entertainment and relaxation areas. The top left features a game room with arcade machines and a dartboard. The top right highlights a manicured putting green. The bottom left displays the exterior of the home with outdoor seating, while the bottom right depicts a home gym with workout equipment against a bright orange wall.

5 out of 5 average rating, 26 reviews

Beachside Bliss w/ Game Room, Gym & Golf Green

The exterior of the vacation home features a welcoming front deck with a table and chairs, shaded by a patio umbrella. A gravel pathway leads to the entrance, complemented by a white panel facade and multiple windows that allow natural light to enter.

4.86 out of 5 average rating, 22 reviews

Beachside @ 455 Seaside

5 out of 5 average rating, 18 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

4.93 out of 5 average rating, 44 reviews

A spacious living area features natural wood beams and light-colored furnishings. A large plant sits in a ceramic vase on a round table, while a comfortable sofa arrangement is placed around a central coffee table. Multiple windows provide ample natural light.

Home in Haddam

The Farmhouse Stay