
House vacation 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

Casino Wine Down House
Friendly and prompt responder. Really clean. The kids more than loved the game room. And I personally loved the decor. Only objection is it’s kinda out of the way and you’d have to drive to do any activities, but other than that a really great stay.

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!!

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
We had an amazing stay and the hosts even went the extra mile for us for some additional requests we had at no extra charge! I would happily return here

Secluded Farmhouse - Studio Apartment Style Unit
Jess’s place was lovely (and so was her recommendation for where to get a great egg sandwich!). We loved reading on the screened-in porch and being within walking distance of two wineries. Hope to be back next year!

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Only complaint would be the noise from road during the morning commute

Beauty and the Beach!
This house is amazing, even more spacious than the photos indicate. Everything was spotlessly clean. The hosts were great communicators, and made sure I had everything I needed. The rooms were nicely furnished and so beautiful. I’d definitely stay here again.

Luxury modern farmhouse with heated pool & hot tub
Exceptional House, lovely property, love the hidden game room! We had a pool tournament going on while we were there. Dining room table, large enough for all of us. Modern well appointed kitchen.

Artist studio in the woods
I had an excellent experience staying at George’s home. He was kind and welcoming and left little notes around the house that were very thoughtful. The art displayed around the apartment was thought provoking and striking. The outdoors area was absolutely breathtaking. He truly has created a special space. I will definitely be back!
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!

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.

Adorable Beach Cottage - Private Beach Association
Sandra’s cottage was exactly as described. It was clean, neat and well appointed. Great location close to the beach, close to the highway and a short ride to shops and restaurants. We would definitely stay again!

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!!

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!

CT River Retreat - Modern Home with CT River Views
This beautiful home practically right next-door to Saint Clemons Castle, right on the water , worked out so perfectly for us and our family with the wedding preparations and such a convenient location! Peter was an absolute pleasure to work with. Communication was excellent and he went above and beyond equipping his place with absolutely everything we could have asked for! Perfectly clean, comfortable, spacious, I can’t say enough good things! It felt like a home away from home. Thank you so much again for everything and For being so accommodating. Highly recommend.!!!
Private house rentals

North Fork paradise between beaches and vineyards
We had a lovely stay at Karine’s cute house! The kitchen was very nicely outfitted, beds were super comfortable, and the big wood-burning fireplace was excellent! We appreciated all the cool artwork around the house, and Karine’s wonderful photography book! We got to enjoy lots of bird life, and we were lucky to have a bit of snow. What a beautiful and peaceful spot. We can’t wait to come back in warmer weather to enjoy the pool and lovely big deck and yard!

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
Katie’s somewhat rustic cottage is right on a beautiful pond, with a beautiful view. It’s cozy and comfortable, and within easy walking distance of downtown Niantic. Katie made us feel right at home. We definitely would stay there again.

Sky of Blue, Sea of Green
We really enjoyed our stay at Carie’s! The house was clean and cute. Our kids loved the game room and hot tub, and the yard was perfect for our dogs. The area is very walkable and lively post-Memorial day. We highly recommend this rental!

Plan your summer getaway! 3 Night Minimum
Unique mid-century mod house design with glass walls viewing the deck & garden, comfortable furniture, fully equipped kitchen, short safe walk to the beach & nearby playground. Responsive hosts. Pristine bathrooms & plush linens. Sauna! Parents of young children may want to block access to the spiral stairs & loft. Older kids will want to hang out in the cool loft! Also perfect for yoga… Great food & brews at nearby Haywire Burger Bar! We plan to return. Thank you Melissa & Patricia

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!

Luxury 5 bed/ 5* beach CT 10 + groups
Fantastic Airbnb. Felt like we were staying at a well taken care of and beautifully furnished home of a friend. Nice art, interesting books, comfy and attractive furniture. The whole house was well furnished. There was a lovely snack basket with fresh fruit, bars, French bread, and delicious local cheese to welcome us. Well stocked kitchen- high quality cookware, lots of cooking basics (spices, etc). But, on top of it all, there was wonderful living space- two full well appointed living rooms each with their own amazing view (one of trees, the other of the pond), a large comfortable yet elegant dining room, a big open concept kitchen with a breakfast table, perfect to do a puzzle, play games or have a quick bite. Plenty of room for our party of 10 adults. Beds were comfy, master suite beyond expectation in size and comfort. Great local market for sandwiches/cookies/coffee. Lovely, local CT beach full of shells. Very responsive host. Stay at this airbnb! Even more beautiful in person.

Beautiful Pattagansett Lakefront w/ Stunning Views
Mitchell was an Amazing host!! He was quick to respond and went out of his way to accommodate arrival and departure time issues I had which helped us out tremendously. I would definitely come back to stay if we come back to this area!! What a beautiful, peaceful, Spacious property. It is exactly what you see in his listing. Lots to do and see, we rode kayaks, enjoyed his entertainment room downstairs and loved that he had phone chargers all throughout the property. It was the perfect venue for us to celebrate our daughter's graduation.
Quick stats about house rentals in Old Saybrook
Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ367 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
- Woodmont Beach
- Amagansett Beach
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Point Judith Country Club
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Blue Shutters Beach
- Bushnell Park
- Bayview Beach
- Long Island Aquarium