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.

4.99 out of 5 average rating, 199 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, 119 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, 197 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, 269 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.

4.92 out of 5 average rating, 331 reviews

Home in Lyme

Stunning, peaceful and private home

Stunning recently renovated 3 story cape on 7+ acres and 2000+ square ft. Open kitchen to living room area with a giant island to gather members of your group together to eat, drink, laugh and have a great time. Cook inside with a fully equipped kitchen, pots, and pans, silverware, spices, everything you would want to prep a great meal as well as a propane grill on the deck. Modern amenities throughout the space. Touch lighting, bluetooth music and more.

4.99 out of 5 average rating, 145 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.

5 out of 5 average rating, 100 reviews

Cottage in Old Saybrook

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.

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.

Guest suite in Old Saybrook

5 out of 5 average rating, 81 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!

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Popular amenities for Old Saybrook holiday rentals

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Other great holiday rentals in Old Saybrook

Superhost

Tiny home in Deep River

4.8 out of 5 average rating, 5 reviews

Her tiny Parisian boat house

LylaRating, 5 stars1 week ago

Hedy’s tiny house was a perfect oasis for some peace! She was incredibly hospitable and even fed me a meal. I loved looking up at the multitude of stars in the sky and listening to all the birds! Would recommend this place if you love interesting stories, peaceful settings and a lot of eclectic things to look at! Had a great time!

Superhost

4.85 out of 5 average rating, 27 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, 39 reviews

Romantic Couples Retreat with Private Sandy Beach

MegRating, 5 stars1 week ago

This is a beautiful private spot. It was so peaceful and quiet. The cottage was very clean, bright with a very soothing color scheme. Lauren was very responsive to any questions we had.

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 stars2 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.

Superhost

Apartment in Old Saybrook Center

4.89 out of 5 average rating, 73 reviews

Seashore getaway - CT shoreline

ScottRating, 5 stars2 weeks ago

Lauren was great and her home was exactly as promised! Great stay and will stay again!

4.97 out of 5 average rating, 36 reviews

Guest house in Clinton

Studio Cottage

MaryRating, 5 stars1 week ago

I felt very comfortable at the charming cottage. Good bed, nice furnishings. Casey was very friendly and welcoming. Really ideal location near my son’s home. Next visit I hope to be able to stay here again. (BTW. Hairdryer did not work )