Cottage holiday rentals in Middletown

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in Middletown

Cottage rentals with a hot tub

Guest favourite
Cottage in Guilford
4.95 out of 5 average rating, 180 reviews

Luxury cottage by the sea with hot tub and pool

ElizabethRating, 5 stars1 month ago
Perfect spot for a quiet weekend getaway! We were able to go to Yale art museums for the day and then came back to check out the beaches. Definitely recommend the trip to Dockside Seafood and Grill in Branford for lobster pasta! The hot tub was also the best way to end the day with a peaceful beautiful view!! Would definitely go back again!
Superhost
Cottage in Norfolk
4.94 out of 5 average rating, 16 reviews

The Cottage at Blackberry River Inn

RohitRating, 5 stars3 months ago
The Cottage at Blackberry River Inn was beautiful and exactly what we needed for the weekend. Breakfast was included and wonderful. This place is a gem and we will be back for sure.
Superhost
Cottage in Litchfield
4.86 out of 5 average rating, 345 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

ZacharyRating, 5 stars2 weeks ago
Took a getaway to Martin's cottage for a long weekend and could not have been happier. It was immaculately clean and the hot tub was ab amazing way to relax. I look forward to being back.
Top guest favourite
Cottage in Plymouth
5 out of 5 average rating, 19 reviews

Lakefront Summer Escape | Cool Tub | Fire Pit

AllysonRating, 5 stars1 week ago
Absolutely stunning views and peaceful vibes at this sweet cottage!!! Totally exceeded my expectations. Book now or you’ll regret it!!!
Cottage in Old Lyme
4.82 out of 5 average rating, 224 reviews

Private Beach Cottage

GraceRating, 5 stars2 weeks ago
Great communication with host, beach within walking distance was so nice, overall good spot within 30 mins of mystic aquarium and Foxwoods casino
Guest favourite
Cottage in Fairfield
4.75 out of 5 average rating, 8 reviews

The Lil Nauti Cottage, Steps To Fairfield Beach

MarilynRating, 5 stars22 months ago
Lil Nauti was perfect for our family. The bedrooms were adequate, with very comfortable beds and plenty of pillows. The wardrobe space and drawers were great as we had a long stay with a lot of baggage! Jason has absolutely everything you could possibly want or need for a stay. The kitchen is really well equipped. Cute cottage and delightful private garden.
Guest favourite
Cottage in Bethlehem
4.98 out of 5 average rating, 104 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AmandaRating, 5 stars2 weeks ago
Kelsey’s home was beautiful and cozy! So peaceful and perfect get away if youre looking to unwind and escape reality for a bit. She was also very kind and accommodating. We decided to go on our mini honey moon after our wedding ceremony took place locally and it was the best decision. She even left us a sweet hand written card that we found upon arrival. Couldn’t have asked for a better place or host to end our wedding weekend! We will definitely be back again.

Pet-friendly cottage rentals

Guest favourite
Cottage in Newtown
4.93 out of 5 average rating, 252 reviews

Private and Serene home close to I-84 and shopping

SherrieRating, 5 stars2 weeks ago
One of the nicest hosts I have ever met. Peaceful area, cute house. Hard to believe that large stores and restaurants are only a few miles away, plus Shake Shack, Trader Joes and Whole Foods. The only problem I had was with my ancient cell phone. I could get test messages, but not phone calls.
Top guest favourite
Cottage in Guilford
4.94 out of 5 average rating, 268 reviews

The Cottage at Indian Cove

ChristineRating, 5 stars5 days ago
Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!
Guest favourite
Cottage in Windsor
4.89 out of 5 average rating, 190 reviews

In-law apartment in Farmington River Cottage

ZamanthaRating, 5 stars1 month ago
I had a great stay at this Airbnb. The place was clean, comfortable, and matched the description perfectly. Communication with the host was smooth and prompt, and check-in was easy. The neighborhood was quiet and convenient, with everything I needed close by. Would definitely recommend and stay again!
Guest favourite
Cottage in Guilford
4.93 out of 5 average rating, 272 reviews

Charm + location. Walk to beach, town, & harbor.

KathleenRating, 5 stars1 week ago
It was so comfortable and peaceful. We had a great time exploring nearby beaches and hikes. We would definitely stay there again.
Top guest favourite
Cottage in Redding
4.93 out of 5 average rating, 263 reviews

Cozy Cottage by the pond

LeeRating, 5 stars2 weeks ago
What a perfect place to explore Southern Connecticut from. Easy to find and easy access to all points of interest. Collis P. Huntington state park is across the street and is an incredible perk. Many easy to walk trails with plentiful wildlife and peaceful serenity. Would recommend and stay again in the future. Jamie is an awesome host, so thoughtful and responsive!!
Guest favourite
Cottage in Milford
4.95 out of 5 average rating, 321 reviews

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

AlyssaRating, 5 stars2 weeks ago
We had a great, comfortable stay here. It was especially nice to be so close to the beach and the restaurants in Walnut Beach. Would definitely stay again!
Guest favourite
Cottage in Cornwall
4.93 out of 5 average rating, 154 reviews

Newly Built Cottage in Housatonic Valley

PaulRating, 5 stars2 days ago
Beautiful place to stay! Kitchen well supplied for cooks. Comfy, big couch. Sound of the river at night. Cute little town. Peace and quiet on the edge of the woods. Great for dogs and humans. Lucy is VERY responsive to any questions. HIGHLY recommended. My wife requested a return visit before we even left.
Guest favourite
Cottage in Sheffield
4.93 out of 5 average rating, 153 reviews

Cheerful 3-bedroom cottage with woodstove.

AvivRating, 5 stars1 week ago
Just like the pictures , very peaceful and serene , the kitchen is well equipped. The beds are comfy. Great place to relax in the Berkshires. With a super responsive host.

Private cottage rentals

Superhost
Cottage in Vernon
4.92 out of 5 average rating, 53 reviews

Churchill Cottage

MarkRating, 5 stars7 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.
Top guest favourite
Cottage in East Haddam
5 out of 5 average rating, 14 reviews

New & Beautiful Lake cottage

SharonRating, 5 stars2 weeks ago
The cottage is on a beautiful lake and is very relaxing . The morning sunset on our second day was amazing. Perfect couples retreat or in our case girls weekend. Our host, Donna, was very responsive and provided extra goodies. The house was clean and comfortable. We visited Gillette’s Castle and downtown Chester had lunch at Market 37 . Unfortunately, we had rain and could not enjoy deck right on the water.
Superhost
Cottage in Colchester
4.92 out of 5 average rating, 91 reviews

The Treehouse at Lake Hayward

MatthewRating, 5 stars1 month ago
We had a wonderful time at Allison's place - the location was great and the property had fantastic amenities that made traveling as a family much easier. Allison was extremely responsive and helpful during our stay. We look forward to returning!
Guest favourite
Cottage in East Haddam
5 out of 5 average rating, 14 reviews

Cozy Lakefront Cottage Perfect for Families

CassidyRating, 5 stars2 weeks ago
What a beautiful view! We had a great time despite the weather. The house was very comfortable and the location right on the lake is hard to beat.
Top guest favourite
Cottage in Branford
4.98 out of 5 average rating, 95 reviews

Enchanted Cottage on the Marsh, walk to beach

MattRating, 5 stars5 days ago
I had a wonderful relaxing time in this charming, well-apportioned cottage. There is a beautiful view over the marsh to short beach and it’s a great spot to see local birds - herons, red-winged blackbirds, etc. A trolley line that’s been converted to a hiking trail runs through the marsh and makes for a great walk. Lots of other fun walks nearby. it’s very quiet and cozy but still just a quick 10 minute jaunt to New Haven The piano and turntable were neat features and the house was nicely maintained and decorated. You can tell the host is very attentive to detail and committed to keeping things pristine. He was also super friendly and responsive I would gladly return to this spot next time Im in the area and heartily recommend to anyone looking to relax and recharge
Guest favourite
Cottage in Lyme
5 out of 5 average rating, 18 reviews

Bucolic Farm On A Country Road

K.K.Rating, 5 stars6 days ago
We could not have asked for a nicer place to stay~~~~clean, comfortable, woke up every morning hearing the bird’s singing. Felt like home. And Lori was a wonderful host! Thank you!
Top guest favourite
Cottage in Clinton
4.98 out of 5 average rating, 98 reviews

Guest House at the Marina

DennisRating, 5 stars9 months ago
We absolutely loved our stay in Clinton! The apartment was beautiful and clean with an amazing view. We tried lots of local hot spots and had a great swim at nearby Hammonasset. Communication and instructions were excellent. We look forward to returning!
Top guest favourite
Cottage in Old Lyme
4.98 out of 5 average rating, 54 reviews

Studio Four-Entire Guesthouse near CT River

ErinRating, 5 stars6 months ago
Our second time staying here. One of our very favorite AirBnBs in the world. Susan and Tripp cover every detail. Place is wonderfully decorated, comfortable and clean. We will be back!

Destinations to explore