Vacation rentals in Old Saybrook

4.89 out of 5 average rating, 399 reviews

A welcoming display includes two wine glasses beside a bottle of wine on a granite countertop. A wicker basket holds assorted snacks, while a blue candle and a bouquet of white tulips add a touch of elegance. An information guide is also visible.

Villa in Norwich

Peaceful Spa Escape minutes to Mohegan Sun Casino

CLEAN-COZY-SAFE-PRIVATE-SPA-WOOD BURNING FIREPLACE Just 3 minutes from Mohegan Sun Casino! This 1 bedroom unit is perfect for solo explorers, couples, girls getaways, or small families looking to experience the excitement of the Casino, while also getting away from it all. Amenities include; 2 seasonal outdoor saltwater pools, jacuzzi, cardio room, and sauna! Beautiful shared grounds w/ The Spa at Norwich Inn and The Norwich Golf Course. Laundry facility onsite. Plenty of free parking!

4.86 out of 5 average rating, 131 reviews

A wooden deck overlooks Johnson's Pond, with a table at the center surrounded by four chairs. Two red cushioned rocking chairs provide a comfortable seating option, and a vibrant red umbrella offers shade. Lush green trees frame the serene water view.

Home in Coventry

Awesome 3 bed vacation lake house. Great location!

Three bedroom house right on Johnson’s Pond with private water access right in the back yard. House features queen master with deck overlooking the pond. 2nd bedroom features a full bed with twin bunk bed above along with a stand alone twin bed. 3rd bedroom has a queen bed. Perfect for one or two couples to share. Full kitchen and laundry along with WiFi and streaming services. Use of 2 kayaks and pedal boat. Just two miles from I-95, so everything in southern New England is just minutes away!!

4.89 out of 5 average rating, 141 reviews

A vacation house is nestled among tall trees, showcasing a multi-level design. Large windows reflect natural light, providing a connection to the outdoors. A spacious deck is partially visible, blending harmoniously with the surrounding wooded area.

Chalet in Goshen

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

4.98 out of 5 average rating, 134 reviews

A serene indoor hot tub is surrounded by wooden paneling and natural stone accents. Soft blue lighting illuminates the water, while greenery is positioned nearby, enhancing the calming ambiance of the space.

Condo in Norwich

The Vacay Villa

The Vacay Villa, just minutes away from Mohegan Sun, Foxwoods and The Spa at Norwich Inn, offers so many amenities you won’t even have to leave the grounds. Private balcony, fireplace, two outdoor pools currently open, year-round access to luxurious hot tub and saunas, small workout room, laundry facilities, pub and upscale restaurant allow for a one-of-a-kind stay at an incredibly affordable price. Why spend hundreds to stay at the area casinos when you can stay in your own private villa?

5 out of 5 average rating, 101 reviews

A well-lit wooden deck features comfortable seating arrangements with padded chairs, perfect for relaxation. Soft lights illuminate the space, creating a welcoming atmosphere. A protective railing borders the deck, with a view of a privacy fence in the background.

Home in Milford

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

4.94 out of 5 average rating, 108 reviews

An open kitchen space features modern appliances, including a stainless steel stove and ample counter space. Barstools are positioned at a breakfast bar, while natural light illuminates the area through several windows. Warm wood flooring complements the neutral-colored walls.

Home in North Fork

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

4.99 out of 5 average rating, 109 reviews

A patio area is set with a round table and four chairs under a large umbrella, offering views of the river. A grill is positioned nearby, and flower planters enhance the space. Lush greenery is visible across the water, framed by a clear blue sky.

Home in Canton

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

4.97 out of 5 average rating, 143 reviews

A covered outdoor seating area is showcased, featuring a sectional sofa and two armchairs adorned with patterned cushions. A coffee table rests on a geometric outdoor rug. The surrounding lush trees provide a serene backdrop, enhancing the tranquil nature of the space.

Home in Smithfield

Luxury Home | Fire Pit | Beach | Grill | 2 Decks

Welcome to Stillwater.House - a custom built Airbnb. Our premier luxury home is situated overlooking a picturesque running river and 92 acre pond. Built in 2020, this beautiful 2,600 sq ft, five bedroom, four bath home boasts breathtaking views, nestled in the picturesque Georgiaville Village. Enjoy the views on TWO decks with plenty of outdoor seating, couches and a brand new gas grill! RE.02492-STR

4.9 out of 5 average rating, 115 reviews

An outdoor deck area is seen featuring a large round table surrounded by several comfortable chairs. A sun umbrella provides shade, while a propane grill is positioned nearby. Lush trees create a natural backdrop, enhancing the serene atmosphere of the space.

Home in Shelter Island

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

4.98 out of 5 average rating, 179 reviews

A spacious living area featuring a comfortable seating arrangement with patterned cushions and a coffee table. Natural light floods through large windows, illuminating the hardwood floor. An adjoining dining area is visible, along with a modern kitchen in the background.

Home in North Fork

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

5 out of 5 average rating, 17 reviews

A spacious deck is shown, featuring several white lounge chairs positioned for relaxation. The view includes a backdrop of gray clouds and an American flag gently waving in the breeze. The coastal home's shingled facade is visible, indicating a classic beach style.

Home in Narragansett

Sunset Sanctuary - Beachfront Vacation Home

Indulge in charming 2-bedroom property with a loft, accommodating up to 8 guests. Step onto the private deck for stunning ocean and sunset views. From coffee on the deck to beach activities, this coastal retreat offers bliss by the sea. Steps away from ocean views and exclusive beach access shared only between owners and guests.

Cottage in Shelter Island

A traditional New England house is set in the central village of the island, surrounded by lush green lawn. Tall trees provide shade, and the late afternoon sun creates elongated shadows across the grass, highlighting the inviting outdoor space.

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

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Popular amenities for Old Saybrook vacation rentals

Laptop-friendly workspace

Stay near Old Saybrook's top sights

Florence Griswold Museum65 locals recommend

The Katharine Hepburn Cultural Arts Center52 locals recommend

The Griswold Inn49 locals recommend

Westbrook Outlets44 locals recommend

Connecticut River Museum38 locals recommend

Big Y World Class Market34 locals recommend

Old Saybrook beach vacation rentals

4.93 out of 5 average rating, 353 reviews

A sunlit view of a sandy beach stretches towards the horizon, with gentle waves lapping at the shore. Colorful umbrellas dot the sandy area, and a wooden walkway runs parallel to the beachfront. In the distance, sailboats can be seen on the calm water.

Home in New London

Amazing Beach House

4.97 out of 5 average rating, 151 reviews

Outdoor seating is arranged on a wooden deck, featuring sleek loungers. Surrounding planters add greenery, while the view stretches to the calm water and distant horizon. Sunlight brightens the area, enhancing the serene ambiance of the beachfront setting.

Cottage in North Fork

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

4.92 out of 5 average rating, 205 reviews

A wide-angle view captures the beach and waterfront community, showcasing houses lined along the shore. A sandy beach meets calm waters, with a jetty extending into the sea. Fluffy clouds float in a clear blue sky above the scenic landscape.

Guesthouse in Milford

Chic Coastal Retreat: Modern Apt Steps from Beach

4.78 out of 5 average rating, 32 reviews

A panoramic view showcases a tranquil beach scene under a double rainbow arching over the sea. Gentle waves lap at the shore, while a sandy beach space with sparse grass is visible. A blue umbrella and chairs provide a welcoming spot for relaxation.

Cottage in Milford

Cheerful 2 bedroom cottage on beach

4.95 out of 5 average rating, 19 reviews

A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.

Home in West Haven

Beach House steps from sand & Amazing Views

4.96 out of 5 average rating, 186 reviews

The image captures a serene view of the ocean from a wooden porch, showcasing calm waters and a sandy beach. A neatly maintained lawn extends to the shoreline, with a few small boats visible in the distance under a clear blue sky.

Home in East Lyme

Beachfront Paradise

4.98 out of 5 average rating, 43 reviews

A shaded porch featuring a gray wooden floor extends towards the water, with hanging planters displaying vibrant flowers. Ocean views are visible in the distance, and a small blue boat is anchored along the shoreline. Soft light creates gentle shadows across the space.

Home in Woodmont

Beachfront paradise- come, stay, relax!

4.97 out of 5 average rating, 274 reviews

A charming outdoor space features a wooden pathway leading to a cozy fire pit surrounded by blue chairs. A vibrant turquoise umbrella provides shade over a nearby table, while a hammock hangs invitingly in the background amidst lush greenery.

Cottage in East Lyme

Your Nest Near The Beach

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Cottage rentals in Old Saybrook

4.93 out of 5 average rating, 211 reviews

Cottage in Voluntown

Lakeside Cottage in the Forest

4.98 out of 5 average rating, 138 reviews

A cozy cottage is presented with a wooden deck and a sloped roof. The deck features a dining table surrounded by chairs. Lush greenery and neatly trimmed bushes surround the pathway leading to the cottage, with a serene lake visible in the background.

Cottage in Hopkinton

Lakeside Cottage in Hope Valley, RI

4.99 out of 5 average rating, 136 reviews

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

Cottage in South Kingstown

The exterior of a charming cottage features a light blue front door and flower boxes with vibrant plants. A welcoming deck is adorned with two blue chairs, surrounded by a landscaped garden filled with daisies and lush greenery.

4.94 out of 5 average rating, 125 reviews

The Snug Cottage: Walk to Water-Newly Renovated

5 out of 5 average rating, 103 reviews

A patio area features dark wicker seating arranged around a low table, with a wood dining set positioned nearby. A large umbrella provides shade, while lush greenery surrounds the space, creating a serene outdoor environment for relaxation.

Cottage in Redding

Star Cottage

4.94 out of 5 average rating, 123 reviews

A quaint country cottage is nestled under mature trees, featuring a large screened-in porch. The property is surrounded by natural landscaping, with a white picket fence partially visible in the foreground. Soft green grass covers the ground, creating a serene outdoor environment.

Cottage in Goshen

Country Cottage in Goshen

4.93 out of 5 average rating, 148 reviews

A modern black cottage is presented, set against a backdrop of tall trees and natural stone landscaping. A gravel driveway leads up to the entrance, where steps ascend to a covered porch. A dog is seen on the grassy area nearby.

Cottage in Cornwall

Newly Built Cottage in Housatonic Valley

Cottage in South Kingstown

A wooden dock extends over calm water, leading toward a charming waterfront dining venue. The establishment features large windows and an outdoor seating area shaded by umbrellas, surrounded by lush greenery and carefully arranged stones along the shoreline.

4.88 out of 5 average rating, 112 reviews

2 BR East Matunuck cottage 7 min walk to beach!

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House rentals in Old Saybrook

4.85 out of 5 average rating, 160 reviews

A charming Cape Cod cottage is showcased, featuring a light gray shingled exterior and blue door. The front yard is adorned with green grass and small shrubs, while steps lead to the entrance. Tall trees frame the property, providing a sense of privacy.

Home in Sag Harbor

Sag Harbor House for rent.

5 out of 5 average rating, 133 reviews

A single-story home is situated on a well-kept lawn with lush greenery and small bushes lining the front. The exterior features light-colored siding and a dark roof, complemented by multiple large windows that enhance natural light.

Home in Cheshire

Pool House

4.95 out of 5 average rating, 230 reviews

A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.

Home in East Hampton

Private beach, fully updated cottage, on 2 acres.

4.94 out of 5 average rating, 134 reviews

A dining room table with eight chairs is set beneath ambient lighting. The room opens to a cozy living area featuring a comfortable sofa and blue curtains. A doorway leads to a well-lit kitchen, enhancing the home's spacious layout.

Home in New London

House in NL near CGA, Sub Base, Mohegan Casino

4.97 out of 5 average rating, 121 reviews

The exterior of a charming two-story house is presented, featuring light siding and dark shutters. Window boxes adorned with blue flowers are visible. A small porch with a door leads into the home, accompanied by a stone pathway and neatly landscaped shrubs.

Home in Old Saybrook

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

4.98 out of 5 average rating, 132 reviews

A two-story home features a grey exterior with white trim and a bright blue front door. Sturdy stone steps lead up to the entrance, flanked by well-maintained landscaping that includes green plants. The property is bordered by a wooden fence, offering privacy.

Home in Westerly

Cute and Close to Beaches and Town

4.99 out of 5 average rating, 101 reviews

A bright living area is illuminated by natural light through large windows. A decorative black wall with a welcome message adds character. A comfortable seating arrangement and dining space is featured. Art pieces are displayed, enhancing the creative ambiance of the space.

Home in Montauk

6 minute walk to Ditch Plains Beach