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 Guilford
4.95 out of 5 average rating, 181 reviews

Luxury cottage by the sea with hot tub and pool

LauraRating, 5 stars2 weeks ago
My friend and I stayed here for a quick two-night getaway and had a great experience. The space is quiet, cozy, and super well taken care of. The view of the water from the living area is beautiful, and we spent both mornings sitting outside with coffee, and afternoons enjoying the view from the hot tub. We appreciated that the kitchen was fully stocked with all the cooking equipment we needed for nights in—and that Mary had a whole list of spots to check out for adventures out (local shops, antique spots, and really solid lobster rolls!) If you’re looking for a low-key, clean, calm place to relax, recharge, and still have easy access to town, this is a great pick. We’d absolutely come back.
Top Guest favourite
Cottage in Burlington
4.98 out of 5 average rating, 119 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

PatrickRating, 5 stars1 week ago
We had a GREAT time at Feyza’s cabin. It was clean, quiet and exactly as described. We especially loved the secluded setting, the lake views and the jacuzzi. Feyza was helpful, communicative and very responsive. Her digital guidebook was very insightful as to the local attractions and restaurants. We would definitely stay here again!
Superhost
Cottage in Litchfield
4.86 out of 5 average rating, 346 reviews

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

LisaRating, 5 stars4 days ago
My boyfriend and I had a nice and relaxing one night stay at Martin’s place. It’s a cute house and we enjoyed relaxing in the hot tub! Martin was responsive and communicative. Overall a nice little getaway.
Top Guest favourite
Cottage in Plymouth
5 out of 5 average rating, 20 reviews

Lakefront Escape | Cool Tub | Game Room | Fire Pit

RamonRating, 5 stars3 days ago
Such a lovely home! actually better than I expected! Will definitely book again. It’s honestly a no brainer after staying there. I can recommend this place 100%!
Guest favourite
Cottage in Bethlehem
4.98 out of 5 average rating, 106 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AmyRating, 5 stars4 days ago
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
4.86 out of 5 average rating, 63 reviews

Lakefront Cottage Complete with Kayaks!

PauletteRating, 5 stars2 weeks ago
Absolutely loved the house on the lake. So well appointed, super clean, kitchen was totally equipped and the surrounding was beautiful and quiet. We highly recommend!
Guest favourite
Cottage in Ledyard
4.93 out of 5 average rating, 254 reviews

Lakeside cottage with beautiful views up the lake!

KerriRating, 5 stars3 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.
Cottage in Cutchogue
4.69 out of 5 average rating, 197 reviews

Lovely 2 BR Beach House No. Shore

MagaliRating, 5 stars3 weeks ago
beautiful house, great location and very nice and peaceful neighborhood close to the beach and the vineyards the house is very well equipped ! Richard was very nice and even find a little bed for our baby boy ! thanks !

Pet-friendly cottage rentals

Top Guest favourite
Cottage in Waterford
5 out of 5 average rating, 21 reviews

Game Room-Mins to Beach&Boardwalk-Walk to Marinas

KatRating, 5 stars6 days ago
Enjoyed my stay in Erin's adorable cottage! Walking distance to great restaurants and the boardwalk. Would definitely stay 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 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 Deep River
4.92 out of 5 average rating, 26 reviews

Serene Waterfront Cottage

RobertRating, 5 stars1 month ago
We love it here! Our home away from home! Since we’ve moved out of Connecticut, this is the perfect place to stay when we come for a visit. Farah is the best host, and we love everything here! Especially her amazing gift basket! Bella always loves her surprises!
Guest favourite
Cottage in Montauk
4.91 out of 5 average rating, 598 reviews

Montauk Oceanview

SusanRating, 5 stars1 month ago
Always love staying at Ron’s. It’s so peaceful. Perfect location and beautiful Ocean views with a short ride if you need to go to town. Montauk Music Fest is a must. Amazing talent and great way to see all Montauk venues. Ron so great to have as a host!
Guest favourite
Cottage in Seymour
4.93 out of 5 average rating, 56 reviews

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

JamieRating, 5 stars1 week ago
My family and myself loved every square inch of this property! From the serene views and well landscaped garden, to the sound of a stream to fall asleep to, the spotless interior and attention to detail…the pet bowls and bed, the labeled cabinets, the toiletries and games, we never wanted to leave! We last minute had to accommodate family members to be picked up later than the check out time and Michael was kind enough to extend our stay until 2pm so we could relax and enjoy more time together! We might make an annual trip out of this house and can’t thank the host enough for his immediate responses and making us feel right at home. Beautiful home, we loved sharing it! The first night we ate at the near by restaurant on the water, Housatonic House, also a recommendation on the fridge! Great food and service and BEAUTIFUL views! It ended up raining Saturday, but we still got a Hike in on our last morning at Osbornedale State Park, beautiful trails and picnic areas! Wonderful time.
Guest favourite
Cottage in Goshen
4.95 out of 5 average rating, 154 reviews

Stuart Cottage/Minutes to Mohawk Ski Area

DeborahRating, 5 stars1 month 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 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.
Guest favourite
Cottage in Westbrook
4.9 out of 5 average rating, 87 reviews

A Beach House Gem

JaimeRating, 5 stars7 months ago
We continue to visit Rose’s house for our yearly weekend girls getaway. It’s the perfect cozy beautiful place to catch up with friends and relax. Rose is an amazing host!
Top Guest favourite
Cottage in Westbrook
4.99 out of 5 average rating, 69 reviews

Beautiful Updated Cottage walk to the Beach

KrisRating, 5 stars1 week ago
Joe’s place was really nice and in a great location. One block from the public beach in Westbrook, it’s in an area where there are lots of great restaurants and cute breakfast places. Joe was proactive in reaching out to ask if I needed anything. Great stay!
Top Guest favourite
Cottage in East Haddam
5 out of 5 average rating, 15 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 stars3 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 stars1 week 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 Rocky Hill
4.98 out of 5 average rating, 52 reviews

Connecticut Waterfront Cottage

JessicaRating, 5 stars1 week ago
The house was beautiful and very nicely renovated recently. Great appliances in the kitchen, comfortable seating in dining area and living room and multiple outdoor areas to enjoy the full river view. The location is right on the water and peaceful but yet only a few minutes to restaurants and groceries. The house is ideal for a couple wanting to have a relaxing getaway. We had 4 adults staying and that pretty much filled the space, especially with only one bathroom. But the bedrooms were a comfortable size and the beds comfy.
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!

Destinations to explore