Cottage vacation rentals in Old Saybrook

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Popular amenities for Old Saybrook cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Guilford
4.95 out of 5 average rating, 177 reviews

Luxury cottage by the sea with hot tub and pool

Jennifer And JonRating, 5 stars3 months ago
We loved this airbnb and stayed for 3 weeks. It sits right on the edge of the marsh with an extraordinary view. We greatly enjoyed how a short walk away is Chaffinch Island, which is a gorgeous park full of tides pools and hackberry trees. The space was clean and comfortable and Mary was a fantastic host. You can see a lighthouse on an island 3 miles out sea from all the rooms, even the main bed.
Top guest favorite
Cottage in Burlington
4.98 out of 5 average rating, 112 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

Mary-CatherineRating, 5 stars4 days ago
Just as listed...small cottage by the water and the view was stunning! I liked relaxing in the swim spa or by the calming lights and sounds of the fake electric fire-- definite cozy vibes! The kitchen is clean and well stocked with utensils etc. Feyza was great about checking in. Thanks!
Superhost
Cottage in East Hampton
5 out of 5 average rating, 3 reviews

East Hampton: Close to The Village and The Beach

JimmyRating, 5 stars7 months ago
I had a wonderful weekend at Andrew’s place in East Hampton. It was gorgeous, perfect location, perfect layout, and such a central location to everything. It was incredibly clean and organized and the backyard was beautiful for relaxing. Andrew was also a terrific host- he left us beverages, was super communicative and flexible and I’m so happy I stayed here. Hopefully I’ll rent again soon!!
Superhost
Cottage in Amagansett
4.87 out of 5 average rating, 23 reviews

4 Br Beach House; Short Walk to Beach!

EveRating, 5 stars3 months ago
Beautiful large home, clean linens, plenty of towels, bathtub worked great. John was very responsive and helpful. Slept 9 people comfortably. The living room area was cozy with an indoor fireplace and the kitchen was large with a large oven and dishwasher. Five minute easy walk to a beautiful quiet beach. Highly recommend this place.
Top guest favorite
Cottage in Plymouth
5 out of 5 average rating, 13 reviews

Summer Escape w/ Cool Tub + Lake Access

AnanyaRating, 5 stars1 week ago
Our family of five loved staying at Yoka and Val's place. The location is very quiet with a peaceful pond across the street. The house itself is very clean and comfortable with everything you need - towels, soap, shampoo, conditioner, coffee and spices - easily available. The beds were also very comfortable. The best part, of course, was the private hot tub in the back yard. It was set in a canopy for extra privacy and wind protection. We loved it. We would definitely stay here again if in the area.
Top guest favorite
Cottage in Narragansett
5 out of 5 average rating, 218 reviews

♥CozyGetaway-Narragansett-15min to Newport-HotTub♛

HayleyRating, 5 stars1 month ago
Amazing stay this weekend at Leann’s place!! Felt right at home & the place was fully stocked with literally everything we could need, she even left us some eggs in the fridge for breakfast! Perfect location, easy to follow instructions, very clean, super responsive! First time stay in RI was everything we could’ve needed for winter wellness weekend. Hope to be back in summer!
Guest favorite
Cottage in Bethlehem
4.98 out of 5 average rating, 101 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AngelinaRating, 5 stars1 week ago
Such a cozy space!!! My small family really did enjoy our peaceful stay. I would definitely book again when in the area. I felt such peace and serenity sitting under the stars, in front of the crackling campfire. It was me and the hubby with 2 of our girls ages 10 and 16. They loved the hot tub and s’mores:). Thanks for the stay.
Guest favorite
Cottage in Woodstock
4.85 out of 5 average rating, 59 reviews

Lakefront Cottage Complete with Kayaks!

JamiraRating, 5 stars2 weeks ago
Place was very well cared for, kitchen and bathrooms were spotless and had everything needed. The views of the lake are GORGEOUS. Felt like home, we had a great time even with the bad weather.

Pet-friendly cottage rentals

Guest favorite
Cottage in Middlefield
4.92 out of 5 average rating, 245 reviews

Lake Beseck cottage

NicoleRating, 5 stars4 months ago
Was the perfect little get away for us. And it was nice to find a place that accommodated the dogs so well. We appreciated being able to get to places easily but at the same time have a peaceful place to return to.
Guest favorite
Cottage in North Fork
4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

RashaRating, 5 stars2 weeks ago
We absolutely loved our quick getaway from the city at Kate’s lovely home. It is hard to articulate in words just how beautiful of a home and location this was. It was truly magical. We were very comfortable as a family traveling with young children. Despite the weather being a bit chilly, we had a wonderful time soaking the views and discovering “treasures” by the water. We cannot wait to come back again soon.
Guest favorite
Cottage in Hebron
4.89 out of 5 average rating, 135 reviews

Welcome to The Holly at Amston Lake

StephanieRating, 5 stars3 days ago
Such a great stay! The area is beautiful, and you can see the water right from the front deck. The Airbnb itself is so cute, with great little touches, like a coffee bar, fire pit, and great views. It was a really peaceful stay, and our pups loved it too.
Guest favorite
Cottage in Charlestown
4.9 out of 5 average rating, 162 reviews

Pet-Friendly Private Beach Oceanfront Cottage A/C

JiaweiRating, 5 stars1 week ago
The place was perfect for us as a weekend getaway: at such peaceful and secluded location, you can really unplug and feel the warmth of the sun and wind from the ocean. Elizabeth was a super responsible and supportive host. Make sure to book if you are looking for a nice vacation at the beach!
Guest favorite
Cottage in Sharon
4.92 out of 5 average rating, 171 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

ChristaRating, 5 stars1 week ago
What a restful beautiful setting. Beautiful views. We really enjoyed watching the hens roam the yard. A super clean space, roomy and comfortable. Some cute towns nearby like Millerton, Hillsdale, Copake, New Preston, Millbrook. Kent Falls close too.
Top guest favorite
Cottage in Fairfield
4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

BriannaRating, 5 stars8 months ago
We enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.
Guest favorite
Cottage in Milford
4.95 out of 5 average rating, 315 reviews

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly

AnnRating, 5 stars1 week ago
We had nice weekend at the cozy cottage. We loved that it was pet friendly and a short walk to the beach. Cameron was very friendly and responsive. She offered great suggestions for food and activities.
Guest favorite
Cottage in Southampton
4.96 out of 5 average rating, 133 reviews

Charming Southampton Light filled Cottage

WirachRating, 5 stars1 week ago
This place is a rare find! Tucked away in a quiet neighborhood, the home is beautifully maintained—spotlessly clean, peaceful, and incredibly comfortable. It was perfect for our family stay, with plenty of space to relax and everything we needed already thoughtfully provided. From the cozy furnishings to the well-stocked kitchen, it truly felt like a home away from home. We especially appreciated the calm surroundings, which made it easy to unwind. We’d happily return and highly recommend it to anyone looking for a relaxing getaway in the Southampton area.

Private cottage rentals

Superhost
Cottage in Vernon
4.92 out of 5 average rating, 52 reviews

Churchill Cottage

MarkRating, 5 stars6 months ago
Frederick and Kelly have a great little rustic cabin right on the lake. Peaceful, quiet (a tiny bit of road noise occasionally, but overall very quiet). Frederick is super helpful and friendly. Cabin was built around 75 years ago (original builder's son left a note in the log book!), so don't expect anything ultramodern.. just a nice unassuming rustic family cabin.
Superhost
Cottage in North Kingstown
4.85 out of 5 average rating, 185 reviews

5-STAR Cove Cottage near Newport - Walk to Beach

DanaRating, 5 stars8 months ago
We absolutely loved the cottage, and we would definitely recommend it to anyone interested in a quiet, cozy cottage in the perfect location😁
Top guest favorite
Cottage in Essex
4.96 out of 5 average rating, 51 reviews

Cheerful, private cottage in Essex village.

LindaRating, 5 stars6 months ago
This was the perfect place for my quick trip to Essex, CT. I was traveling alone and this little one bed/one bath was great for my needs. It was a little challenging to find at first, but once you figure it out, it's easy peasy - and I appreciated that it's set so far back off the street. The house is close enough to town that you can walk if you want to, and it's just an overall great location. I'll be back!
Superhost
Cottage in South Kingstown
4.79 out of 5 average rating, 108 reviews

Wash Pond Cottage

MichaelRating, 5 stars7 months ago
A true getaway weekend at Wash Pond house. The scenery is beautiful from the large deck overlooking the pond, right down to the dock at the base of the water. The rustic cottage's soothing atmosphere in this secluded area is everything one could ask for. The house has all the essentials and more to make you feel right at home. Katrina is an incredible host; friendly, helpful and attentive. I highly suggest the Wash Pond experience.
Guest favorite
Cottage in Voluntown
4.93 out of 5 average rating, 211 reviews

Lakeside Cottage in the Forest

JaniceRating, 5 stars2 weeks ago
We had such a wonderful stay at this cabin! The owner was incredibly friendly and welcoming, and it was clear from the moment we arrived that they had put a lot of thought into making the place comfortable and easy to enjoy. The cabin was spotless, beautifully maintained, and had everything we needed for a relaxing getaway. One of the things we appreciated most was the detailed binder the owner provided—it included a map of the property, local tips, and great information about all the activities available right on site. It made exploring super easy and fun. We especially loved kayaking with our friends—it was such a peaceful and memorable part of the trip. Between the beautiful surroundings, the well-equipped cabin, and the thoughtful touches throughout, we couldn’t have asked for a better experience. We highly recommend this spot to anyone looking for a cozy, activity-filled, and well-cared-for place to stay!
Superhost
Cottage in Winsted
4.89 out of 5 average rating, 35 reviews

Cottage Ease.

KurtRating, 5 stars6 months ago
This cute cottage’s was exactly what we were looking for. Our stay was short but Meredith gave us great suggestions for places to eat to help us avoid wasting our minimal time searching. On a fall weekend the neighborhood was quiet. It was a really nice weekend stay for us.
Superhost
Cottage in Narragansett
4.92 out of 5 average rating, 13 reviews

Beach Cottage Located in Private Beach Community

SpencerRating, 5 stars8 months ago
Mary’s place was great! Everything was clean, the place was walking distance to the beach, and it was the perfect size for 2 people. Would stay here again! Note: Make sure to bring your own shampoo and body soap. It says on the listing that soap is included but when we arrived there was only hand soap and nothing for the shower which wasn’t a big deal since we had packed some.
Guest favorite
Cottage in Deep River
4.91 out of 5 average rating, 23 reviews

Serene Waterfront Cottage

RobertRating, 5 stars5 months ago
As always, we love our stay at the cottage. It’s becoming our home away from home when visiting our son. Thanks for all our goodies! Always a great surprise! Have a wonderful Christmas. We’ll see you next year I hope.

Quick stats about cottage rentals in Old Saybrook

  • Total rentals

    20 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    650 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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