Holiday rentals in Old Saybrook

4.89 out of 5 average rating, 160 reviews

Cottage in Westbrook

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

5 out of 5 average rating, 200 reviews

Guest house in Portland

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Cottage in Old Saybrook Center

4.98 out of 5 average rating, 120 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.

4.89 out of 5 average rating, 198 reviews

Flat in Old Lyme

Private apartment in historic Old Lyme mansion

3rd floor apartment in Ludington House, a historic home centrally located in the charming village of Old Lyme. 3 bedrooms (2 queen, and one with two twin beds/trundle), 2 full bathrooms. Close to restaurants, beaches, art galleries and museum. Please do not book for a group that does not include yourself. Person booking the apartment must be one of the guests staying. We do not allow guests that are not part of the reservation to visit the property during your stay.

4.98 out of 5 average rating, 270 reviews

Home in Lyme

“The Answer” Your Unique, Tidal, Riverfront Escape

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil tidal water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

4.99 out of 5 average rating, 146 reviews

Cottage in Waterford

Coastal Cottage Private Studio

Beautiful coastal studio cottage located on the shoreline of CT. Your cottage is spacious and private with keyless entry and private dedicated parking. Originally an art studio, this recently renovated cottage is one mile to the beaches and local attractions. Our cottage is popular among Connecticut College, Coast Guard Alumni/parents and for anniversary celebrations! Enjoy...Now you can kick back and relax... you've found your home away from home! 🤩🏡 😊

Cottage in Old Saybrook Center

4.97 out of 5 average rating, 74 reviews

1920’s charming dollhouse near South Cove

Simple, no frills guest cottage near South Cove in Old Saybrook. Drop your kayak /paddle board in at the end of the street, walk to town for dinner or a show at the Katherine Hepburn Theater, or enjoy a day at town beach only 1.5 miles away. This is a shabby chic escape in a friendly, quiet neighborhood. A few quirks but tons of charm! If you are looking to unplug and sit by the fire pit, read a book, and go to the beach, this is the place for you.

Home in Old Saybrook Center

4.72 out of 5 average rating, 223 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.

4.97 out of 5 average rating, 274 reviews

Cottage in East Lyme

Your Nest Near The Beach

Welcome to A Shore Thing, a retro modern beach cottage. This bright and cheerful escape is perfectly located for exploring the shoreline. Whether you are visiting in the summer for sun, surf and sand or in the quieter off-season, you will find the shoreline is packed with an incredible array of inviting destinations. The cottage is just 3/4 of a mile from the beautiful private sandy beach.

4.94 out of 5 average rating, 442 reviews

Loft in Essex

Unique apartment in former art gallery.

The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. We gladly welcome clean, well behaved pets for an extra fee of $50. Pet sitting and dog walking also available for an additional fee. On site babysitting also available for an additional fee.

Guest suite in Old Saybrook

5 out of 5 average rating, 82 reviews

Cozy Loft Getaway

Our private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

4.96 out of 5 average rating, 136 reviews

Tiny home in East Lyme

Modern Waterfront Tiny House

Welcome to Your Lakeside Wonderland! Tiny House, Huge Charm! Tiny in Size, Grand in Experience: Nestled on the serene shores of Pattagansett Lake, our brand-new tiny house offers a magical escape. Compact yet bursting with all the comforts of home, this little gem is a marvel of modern living in a cozy package.

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Popular amenities for Old Saybrook holiday rentals

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Other great holiday rentals in Old Saybrook

4.71 out of 5 average rating, 7 reviews

Tiny home in Deep River

Her tiny Parisian boat house

DeeRating, 5 stars1 week ago

I loved my stay--a Zen retreat. Cozy bed and desk workspace, charming decor. Beautiful backyard--spacious, colorful decor, lush with greenery (there's a pool too!). Hedy is super friendly and in the know in for things to do in the area, so definitely ask her how to spend the day at Deep River and other notable sites.

4.86 out of 5 average rating, 28 reviews

Newly renovated CT shoreline home next to Marinas

BobRating, 5 stars1 week ago

Michael and Alyssa’s property was as described - actually felt more spacious than we expected. The layout was perfect for our party and TV/Wi-Fi facilities were excellent. The weather was inhospitable but they can’t be blamed for that!

5 out of 5 average rating, 40 reviews

Romantic Couples Retreat with Private Sandy Beach

RajRating, 5 stars2 weeks ago

Fantastic cute spot in Old Saybrook. Key things for future guests to know - there is no A/C in the winter months so the air can get a bit stale / stuffy in the house. Plus there is no washing machine / dryer in the house, so defo bring enough clothes!

5 out of 5 average rating, 16 reviews

Cornfield Point Beach House View

DonnaLynnRating, 5 stars5 months ago

Chloe's home was perfect for our stay as we wanted to be near my son in Old Saybrook. She was responsive and accommodating with my questions and needs always getting back to me right away. Check in was easy and I received emails all along the way which was helpful as I am a first time airbnb person. The home was immaculate with everything as it said it would be. I would definitely stay again and recommend this home.

4.94 out of 5 average rating, 52 reviews

Water Views and Walk to Beach

VictoriaRating, 5 stars3 weeks ago

We were in Connecticut for our nephew's graduation from Yale. While searching for a house that could accommodate 8 people, I came across this beautiful home. When arriving and walking into the house, it exceeded all of my expectations. It was absolutely gorgeous and only a few steps to the beach. Our family could not stop talking about how exceptional the house was. The little town of Old Saybrook was so cute as well. I would highly recommend this amazing house to anyone that is staying in the area. Trust me, you will not be disappointed.

4.95 out of 5 average rating, 38 reviews

Guest house in Clinton

Studio Cottage

KellyRating, 5 stars1 day ago

Looked just like the photos. Private space. Clean and tidy, had a few essentials including coffee! She was very responsive and gave East to follow directions for checking in. Provided great recommendations for nearby places. Location was exactly what we were looking for. Would highly recommend.

5 out of 5 average rating, 52 reviews

Great Hammock Getaway | Beaches, Views & Hot Tub

JoanaRating, 5 stars4 weeks ago

We spent a few days at this amazing place and absolutely loved it! The house is cozy, very clean, well-organized, and beautifully decorated – great taste in every detail. We especially enjoyed the hot tub and the fireplace – perfect spots to relax. The location is also excellent. The host provides bikes, and we used them to explore the nearby beaches and ride around the town. It was exactly the peaceful and relaxing break we needed from our busy routine. We would definitely come back! ♥️