Cottage holiday rentals in Old Saybrook

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in Old Saybrook

Cottage rentals with a hot tub

Guest favourite
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 favourite
Cottage in Burlington
4.98 out of 5 average rating, 112 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

Mary-CatherineRating, 5 stars2 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 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 favourite
Cottage in Plymouth
5 out of 5 average rating, 13 reviews

Cozy Lakefront Retreat | New Backyard & Hot Tub

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.
Guest favourite
Cottage in Bethlehem
4.98 out of 5 average rating, 101 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AngelinaRating, 5 stars5 days 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 favourite
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.
Guest favourite
Cottage in Ledyard
4.93 out of 5 average rating, 248 reviews

Lakeside cottage with beautiful views up the lake!

JimRating, 5 stars2 weeks ago
We had a relaxing, peaceful time at Bobby's place. It's wonderful to wake up right on the water. He was very communicative. It is quiet, but still close enough to everything. We had an enjoyable experience.
Cottage in North Fork
4.69 out of 5 average rating, 195 reviews

Lovely 2 BR Beach House No. Shore

KateRating, 5 stars6 months ago
Great spot for a long weekend! Wonderful location close to the beach and local wineries. Richard was a great host offering lots of recommendations and clear instructions for check in and using available amenities.

Pet-friendly cottage rentals

Guest favourite
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 favourite
Cottage in Hebron
4.89 out of 5 average rating, 135 reviews

Welcome to The Holly at Amston Lake

StephanieRating, 5 stars1 day 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 favourite
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.
Superhost
Cottage in East Hampton
5 out of 5 average rating, 14 reviews

Bright Zen Beach Cottage, Pool Access, EV Charger

TamaraRating, 5 stars10 months ago
Simply put - A perfect stay! Jami’s home is peaceful and beautiful and in an ideal location in Easy Hampton. We felt very welcomed and ‘at home’ for our entire stay. Jami is also an excellent communicator. Thank you very much much for sharing your home with us, Jami. We will be back :)!
Guest favourite
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.
Top guest favourite
Cottage in Redding
4.93 out of 5 average rating, 259 reviews

Cozy Cottage by the pond

MaryEllenRating, 5 stars1 week ago
My husband and I had a great stay. James and Rose are super helpful hosts. It’s a great place to relax and enjoy nature. Walking distance to a lovely park they recommended with tons of hiking trails and very quiet.
Guest favourite
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 favourite
Cottage in Westbrook
4.89 out of 5 average rating, 154 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

DamienRating, 5 stars5 days ago
We stayed here as we needed a stop over. The house is isolated and the terrace overlooking the river is fully private. We had a great time sitting outside and enjoying the peace. Bonus: it’s walking distance to the nearest beach. Would recommend and stay here again.

Private cottage rentals

Superhost
Cottage in Deep River
4.73 out of 5 average rating, 240 reviews

Cottage overlooking the CT river

JoanneRating, 5 stars4 months ago
Very quaint and happy little house. Everything you need is supplied. Bed is comfy. A super nice place to be.
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.
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.
Top guest favourite
Cottage in North Fork
4.97 out of 5 average rating, 38 reviews

New Suffolk Beach Cottage 1 | North Fork

DouglasRating, 5 stars7 months ago
The beach house was great. Instead of being on a road, it was on a green commons area that gave it a really relaxed neighborly feel. It was a very easy and pleasant 1 minute stroll to the beach, where was a great pastry and shop, and restaurant, and some simply amazing views. Deb's communications were also great and check in went amazingly smoothly. Also the town of New Suffolk itself is quite charming, and is a perfect base for exploring vineyards, beaches, hiking trails and whatnot.
Superhost
Cottage in North Fork
4.92 out of 5 average rating, 52 reviews

Beautiful cottage on East End

AshleyRating, 5 stars4 months ago
Vincent’s place was great for my husband, myself, our baby and my parents to stay when visiting Jamesport for a wedding. Beautiful cottage, close to everything, and Vincent was very easy to communicate with. Would stay here again
Guest favourite
Cottage in Old Lyme
4.88 out of 5 average rating, 40 reviews

Renovated beach cottage a block from private beach

EllenRating, 5 stars8 months ago
April’s cozy beach cottage was perfect for my elderly parents. Everything was spotless, and although tiny, the kitchen was fully stocked with a large refrigerator and full stove, microwave etc. both the bed and the sofa were v comfortable and most importantly, April made sure there was AC in every room, even the cute porch. There’s an outdoor shower which is super convenient. You can easily walk to the beach, go to the arcade, kokomos, a crepes place and the carousel and gift shop. Very peaceful retreat. Must also mention how cheerfully it’s decorated and how spotlessly clean! Just lovely.
Guest favourite
Cottage in Guilford
4.86 out of 5 average rating, 37 reviews

Your own Thimble Islands private cottage!

LilianRating, 5 stars1 week ago
We had an amazing stay with Sean and Jenny. The property is perfect for a peaceful getaway from the stresses of daily life- unique location, impeccable views, spotless and well furnished house, we were able to unplug and enjoy some nice quality time. Sean is a gracious host, offered lots of local recommendations as well as details of the house that were very helpful. Was responsive for questions and easy to communicate with. Hope to be back one day!
Superhost
Cottage in Westbrook
4.52 out of 5 average rating, 21 reviews

Remodeled Cottage Private Old Kelsey Point Beach

JillRating, 5 stars9 months ago
Cheryl's place was adorable! I felt right at home in the cosy open concept living space. My mom crashed the weekend portion of the trip which was nice. My cat Mushu had a wonderful time and we even went outside. The beach was about a four minute walk for me, and a breathtaking view as you approach. Cheryl had everything necessary and mentioned. Next time I'll be sure to bring coffee filters and sugar. There were unexpected amenities too like paper towels and trash bags, and candles. There were also tons of spare toiletries like shaving cream and shampoo and conditioner and body wash. Thanks again!

Quick stats about cottage rentals in Old Saybrook

  • Total rentals

    20 properties

  • Nightly prices starting at

    £60 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

Destinations to explore