Cottage vacation 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 favorite
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 favorite
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 favorite
Cottage in Plymouth
5 out of 5 average rating, 20 reviews

Lakefront Escape | Cool Tub | Game Room | Fire Pit

RamonRating, 5 stars2 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 favorite
Cottage in Bethlehem
4.98 out of 5 average rating, 106 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AmyRating, 5 stars3 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 favorite
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 favorite
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 Old Lyme
4.82 out of 5 average rating, 224 reviews

Private Beach Cottage

GraceRating, 5 stars3 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

Pet-friendly cottage rentals

Top guest favorite
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 favorite
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 favorite
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 favorite
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 favorite
Cottage in Montauk
4.89 out of 5 average rating, 491 reviews

Montauk Oceanview with Fireplace

LaurenRating, 5 stars1 month ago
Great spot. Close to town and quick walk to beach. Can’t beat an ocean view from the living room.
Guest favorite
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 favorite
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.
Top guest favorite
Cottage in Old Saybrook
4.97 out of 5 average rating, 74 reviews

1920’s charming dollhouse near South Cove

HilaryRating, 5 stars3 weeks ago
The cottage was fantastic, and Jodi was an amazing host. Communication was effortless and timely, and Jodi was helpful, proactive and generous. I loved how close the sound was to the cottage - hopefully I'll be able to stay there again, and if I do I'll bring a kayak with me. For the purposes of this stay, though, maybe the best thing was how close it was to where I was working for the week - less than a 5-minute drive to downtown Old Saybrook.

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 favorite
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!
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 favorite
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 favorite
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 favorite
Cottage in Guilford
4.99 out of 5 average rating, 103 reviews

Waterfront Joshua Cove Cottage with private beach.

KitRating, 5 stars4 days ago
A truly lovely spot! Quiet, relaxing and comfortable. We enjoyed the view of the water, reading on the patio in the lounge chairs and sitting on the bench overlooking the beach. We would love to come back again.
Top guest favorite
Cottage in Clinton
4.97 out of 5 average rating, 31 reviews

Cottage at the Marina

CarolRating, 5 stars8 months ago
My stay at Chris and Ann’s listing was the perfect last stop on my stay in CT……beautiful, welcoming accommodations enhanced by the natural, peaceful, setting of the salt marsh and wildlife. It’s absolutely a favorite place the next time I’m visiting CT.
Top guest favorite
Cottage in Old Lyme
4.98 out of 5 average rating, 55 reviews

Studio Four-Entire Guesthouse near CT River

JoshuaRating, 5 stars3 weeks ago
Very private nicely appointed and great hosts

Destinations to explore