Cottage holiday rentals in Middlesex County

Find and book unique cottages on Airbnb

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Popular amenities for Middlesex County cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

JenRating, 5 stars2 weeks ago
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!
Top Guest favourite
Cottage in Burlington
4.98 out of 5 average rating, 118 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

KimberlyRating, 5 stars2 weeks ago
I went here on a peaceful getaway with my partner for my birthday , and it was better than anything I could've imagined. exactly what we needed and even more beautiful in person than in the pictures! We had multiple questions for Feyza and she always answered very promptly. was such a clean spacious and peaceful getaway. couldn't have asked for more 😭
Superhost
Cottage in East Hampton
5 out of 5 average rating, 4 reviews

Walk/Bike to East Hampton Village & Ocean Beaches

JimmyRating, 5 stars8 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 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 Escape | Cool Tub•Game Room•Dog-Friendly

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!!!
Guest favourite
Cottage in Bethlehem
4.98 out of 5 average rating, 106 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AmyRating, 5 starstoday
I wanted a weekend getaway for my son’s 13th birthday that landed on Friday the 13th, I came across this cabin airbnb and decided to book and give it a try. this location is an hour away from our home and gave us that peace of paradise we were looking for. the cabin felt like home and had everything you can possibly need. I honestly wish I can give higher than a 5 star because this cabin was perfect. I’ll be booking again for a winter weekend getaway. thank you for hosting my family and I.
Guest favourite
Cottage in Woodstock
4.85 out of 5 average rating, 62 reviews

Lakefront Cottage Complete with Kayaks!

AnnieRating, 5 stars4 weeks ago
Our stay at this lakeside retreat was perfect! The house was exactly as described, with stunning views that exceeded expectations. Mornings with coffee and evenings with cocktails on the back porch became our favorite ritual. The picturesque fire pit and thoughtful touch of Hershey bars for s’mores were delightful, though we didn’t get to use them this time. Our host was incredibly responsive, quickly resolving a hot tub issue, and their winery recommendations were spot-on! Quick tip: If arriving after dark, keep exterior lights off initially to avoid lakeside gnats. We noticed a few stink bugs on day one (nature’s welcome!), but they completely disappeared afterward. Neither affected our enjoyment of this beautiful property at all. Thank you for an unforgettable stay!​​​​​​​​​​​​​​​​
Guest favourite
Cottage in Ledyard
4.93 out of 5 average rating, 254 reviews

Lakeside cottage with beautiful views up the lake!

KerriRating, 5 stars2 weeks ago
We always love going to this cottage. It’s our favorite. It’s actually one of our favorite places. To go a few times a year winter summer. We just spent memorial weekend there. A little doggies loved it. Home away from home so cozy. Bobby the host is wonderful. My daughter boyfriend came up and they absolutely loved it and my son came from Texas to spend one night. It was his first time there he loved it. We already planning on going back. Fantastic getaway. If you need to distress and want calmness. This is the place to come to. And the town of Mystic has great restaurants Like I said it’s our favorite place to come to and I’ve been to quite a few…. Just got home today and I’m seeing if I can book some sometime in October to go back we love it.

Pet-friendly cottage rentals

Guest favourite
Cottage in Riverhead
4.97 out of 5 average rating, 154 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

BrettRating, 5 stars1 week ago
Look no further! The Beach Cottage is beautiful, immaculate, private, and all things one would hope a vacation getaway would entail. This location feels “off the grid” albeit close to modern amenities/stores. Hope to be back soon!
Top Guest favourite
Cottage in Sharon
4.93 out of 5 average rating, 181 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

JenniferRating, 5 stars5 days ago
This is our second time staying at Foxfire Hill, and it was wonderful to see the gardens in their glory. Great and responsive hosts. I’m sure we will be back again.
Top Guest favourite
Cottage in Ledyard
4.91 out of 5 average rating, 112 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

OliviaRating, 5 stars1 month ago
My sister, dog and I stayed at the cottage for the weekend and had a great experience! Erika is a wonderful host and the property is beautiful. The cottage itself was exactly as pictured. Breakfast in the inn, cooked with natural and organic ingredients, is an absolute must. The location of the inn is great as well, with direct access to the Lantern Hill trail (which our dog loved) and only a short drive from downtown. Would definitely recommend staying here!
Guest favourite
Cottage in Windsor
4.9 out of 5 average rating, 191 reviews

In-law apartment in Farmington River Cottage

GaryRating, 5 stars5 days ago
Is a great place. Clean, comfortable. It is a basement apartment so the ceilings and doorways are lower than a normal house. I am 6 ft 5 in tall and I did not hit my head on the ceiling but the doorways were low where my hair would brush up. The bathroom sink and mirror were low also but all things were workable. I am NOT faulting her place at all. I am just tall. I will stay here again on my next trip to Connecticut. Elizabeth is nice and friendly. Once in a while you would hear the cat chasing the dog upstairs. but I just laughed at it. No noise was ever constant or non-stop. Slept very well. The early evening you would hear a train whistle way in the background almost like clockwork. Not disturbing, made it peaceful like you were in a small town country place. The river was nice. Hearing the river and wildlife was nice after a 10 hour workday. Highly recommend this for a stay. Only thing- wish the security light went on at 3am when I left. Hard to see going up the outside stairs.
Guest favourite
Cottage in Milford
4.95 out of 5 average rating, 103 reviews

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

OliviaRating, 5 stars1 month ago
A very cute and wonderful place to stay! Cozy, clean, private, and incredibly close to the beach! Lisa was extraordinarily understanding about the check-out time and process, would LOVE to stay again! :)
Guest favourite
Cottage in Montauk
4.9 out of 5 average rating, 296 reviews

Montauk Cottage 5

AngelRating, 5 stars6 days ago
Ron responded extremely quick to one of my requests. He also gave us some great restaurant recommendations of which we ended up going to. Overall smooth, enjoyable, and worry free stay.
Guest favourite
Cottage in Goshen
4.95 out of 5 average rating, 154 reviews

Stuart Cottage/Minutes to Mohawk Ski Area

DeborahRating, 5 stars4 weeks ago
This cottage is the perfect quiet getaway to escape from the city. It is perfectly situated between Litchfield, Kent, and Cornwall where there is more to do than can be counted. It is a perfect spot, especially in spring or fall, but of course winter would be nice too with all the snow.
Top Guest favourite
Cottage in Old Saybrook
5 out of 5 average rating, 100 reviews

Cozy Waterfront Retreat

IrisneriRating, 5 stars1 month ago
Meghan's place is exactly as posted it is absolutely beautiful, cozy, comfortable and did I say beautiful? one of my favorite things to do was sit in front of the big windows and read. You have everything you can think of close, at least 4 to 6 minutes away. There are restaurants, super market and pharmacies. But if you are like me and also like to cook sometimes on vacation the kitchen was equipped with everything you need. Highly, highly recommend.

Private cottage rentals

Superhost
Cottage in Portland
4.61 out of 5 average rating, 18 reviews

Lake Cottage Getaway

NanaRating, 5 stars8 months ago
Had a really wonderful time here for my friends’ trip. Kimberly was a communicative and amazing host, and the cottage was clean and well-stocked. The location is also perfect if you are hoping to enjoy some peace and relaxation, with nearby parks and trails available for exploration.
Top Guest favourite
Cottage in East Haddam
5 out of 5 average rating, 14 reviews

New & Beautiful Lake cottage

SharonRating, 5 stars3 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.
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 Madison
4.94 out of 5 average rating, 33 reviews

Adorable cottage close to beaches and downtown

YaoRating, 5 stars3 weeks ago
My family were coming to the commencement so we stayed at John’s place for several days. The house is at a very quiet place surrounded by woods yet easy to find from the main road, and has easy access to I-95. The house was bigger than we thought and can accommodate six or even more people. It has everything we need like dishwasher, washer and dryer, etc. John also kindly provided grounded coffee and drinks in the fridge. It was an excellent experience!
Guest favourite
Cottage in Lyme
5 out of 5 average rating, 18 reviews

Bucolic Farm On A Country Road

K.K.Rating, 5 stars1 week 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!
Guest favourite
Cottage in Collinsville
4.97 out of 5 average rating, 140 reviews

The Carriage House

AlyssaRating, 5 stars4 weeks ago
Kristen was awesome and made us feel very comfortable. We loved walking around the trails and exploring. We will definitely be booking with her again when we come back!
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