
House holiday rentals in Old Saybrook
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Top-rated house rentals in Old Saybrook
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Popular amenities for Old Saybrook house rentals
House rentals with a pool

Homestead Near Mystic, Casinos & Beaches
This was the perfect spot for what we were looking for as my son graduated from Conn College. The host was very responsive to my questions and flexible with check in times which we needed. House was exactly what was described and we had a wonderful time. Thank you!!

Casino Wine Down House
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

Stylish+Modern Cape w/Saltwater Pool-5min to Beach
Great spot in Hampton Bays! The house was as described and in a very cute and walkable neighborhood. Super close drive to the beach and a couple of local restaurants and eateries. Loved how private the spot felt too! David’s done a wonderful job with the backyard, so you get the comfort of having close neighbors without the intrusiveness. Pool was awesome. We definitely enjoyed it!

4BR Private Indoor Heated Pool - Lux Mystic Home
Enjoyed our time at Jason’s house. My family really enjoyed the warm pool along with all the pool toys. Our host provided good information as well as being responsive to any questions. The house was very clean and beautiful.

Midcentury Modern ZenHouse Sculptor Studio
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
AJ's home was great for our one night stay. The hot tub and outdoor patio were our favorites, and the interior also did not disappoint! AJ was a friendly and communicative host.

Secluded Farmhouse - Studio Apartment Style Unit
Jessica's place was serene and exactly what we were looking for during our long weekend in the North Fork. Great communication!

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes
We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.
Weekly house rentals

Adorable Beach House on LI Sound
Had an excellent stay at Eileen’s place. The house was extremely clean and perfect size for a couple. Beautiful view and surroundings. Only wish I had more time to explore the area. Would definitely stay here again if I return.

The Beach House (Costa Casa Pelo Mar)
Rosemary’s house is beautiful and was perfect for our stay! There was 8 of us and it was just right!

Zion's Light Beach Cottage
We had a great stay at this cottage- it was a perfect size for our family and was extremely clean, warm and comfortable. We especially enjoyed the quick walk to the beach, and proximity to town. Hosts were very friendly and responsive but never intrusive. Would highly recommend.

Adorable Beach Cottage - Private Beach Association
Sandy and Ian were perfect hosts! Quick to respond to any queries and extremely welcoming. The cottage was clean and well stocked with all needed supplies. I cannot express how happy we were with our stay. Thank you once again Sandy and Ian for making our stay comfortable and stress-free!

Money Point Beach House- Deck+Views + Beach Access
Had a great 5 day stay. The homes description matched perfectly and the host was very responsive. The fenced in back yard was ideal for our 2 dogs and the area was very peaceful.

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!

Stylish Retreat Waterviews
From the kayaks to the coffee, our stay was glorious! I loved waking up every morning to the gorgeous view of the Niantic River. The indoor and outdoor spaces were comfortable and there are so many amenities. Location is perfect- a short walk to the boat dock and back entrance to the Oswegatchie Hill Trail. I’d love to go back!! Thank you Cindy!

Mid-Century 4 bedrooms with Water View & Access
We had a wonderful weekend at Aude's home in Essex. The setting was beautiful and the house itself was immaculate. It is a 7 minute drive to the center of town, which was convenient. The host was very responsive and quick to fix any concerns we brought to her attention. I would definitely return to this Airbnb!
Private house rentals

The Bay Cottage · Rocky Neck Park, Beach & Niantic
Such a lovely get away! My friends and I only stayed a night but it made us wish we could’ve stayed longer!! Thank you!

Stunning house on CT river !
We did enjoying when staying Marina's house. The place was beautifull, clean and cozy. Very recommeded!!! Thank you for letting us stay in your lovely nest!

Lakeside bliss
We had an absolute PERFECT stay here! First off- the house. This home is so charming in every way. We loved the way it’s decorated and laid out, and it’s so cozy, clean and beautiful. You are truly able to relax here. Also, the bed is extremely comfortable, the water pressure is great, and the A/C works very well. However, perhaps the best part of this house is the view! There are sliding doors in the living room and bedroom, and the view of the lake is breathtaking. The area is super safe and quiet, and you are in walking distance to downtown Niantic and the Boardwalk which you cannot beat! Also only about 20 minutes from Mystic. I cannot forget to mention how amazing our host, Katie, was! Super attentive and responsive with messaging, and she was even here doing yard work when we arrived so she greeted us which was such a nice touch. Overall, we will DEFINITELY be looking to stay here again! Loved every minute of it.

Boulder Lake House Retreat
The Boulder Lake House was absolutely beautiful. The photos do not do the home justice. They have everything you can possibly need inside and it was immaculately clean! We traveled with our 2 & 4 year olds who are very particular about things & they loved the house. Made themselves right at home. The amenities were endless and the kitchen was a treasure to use; we ate home for every meal. We had an issue with the deck door & owner was at the house within 20 minutes to help. Very respectful & helpful. I would definitely reserve this house in the future.

Sky of Blue, Sea of Green
I am so happy we found Carie's place! We are a band on tour right now and had such a relaxing time. Hot tub was perfect. Kitchen had everything we needed for a home cooked meal. Instructions were clear and easy to follow. Easy check-in/check-out. Thank you so much!

Essex village carriage house
Wonderful stay! Close to beautiful historic downtown Essex. Short walk to coffee shop in the morning and dinner at night! Kayaking in Long Island sound! Great biking! Super clean, well decorated. Everything was new and Very cozy! Perfect couples getaway in the lower Connecticut valley!! Highly recommend!

The Farmhouse Stay
Chelsea was communicative and helpful about her beautiful house. It had all we needed, was well appointed, beautifully decorated and in a gorgeous natural setting. We spent time lounging in the living room as a family and it was so comfortable. Top notch! Grab this place now!

Sunset Skies 2nd Fl | redone+walk to Water’s Edge
Great stay! One of the best AirBnB accomodations we have visited; everything was perfect! The location is ideal to walk to Water's Edge Resort or downtown Westbrook, very close to the beach. The stay was beautiful with brand new amenities, exactly as described. Kelly was very responsive, kind and helpful with any questions we had. We cannot wait to stay here again for a future stay.
Quick stats about house rentals in Old Saybrook
Total rentals
90 properties
Nightly prices starting at
$166 NZD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Point Judith Country Club
- Amagansett Beach
- Seaside Beach
- Blue Shutters Beach
- Quotonset Beach
- Ninigret Beach
- Bushnell Park
- Jennings Beach
- Silver Sands Beach
- South Jamesport Beach
- Groton Long Point Main Beach