Cottage vacation rentals in Middletown

Find and book unique cottages on Airbnb

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Popular amenities for Middletown cottage rentals

Cottage rentals with a hot tub

Guest favorite
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 favorite
Cottage in Plymouth
5 out of 5 average rating, 19 reviews

Lakefront Summer Escape | Cool Tub | Fire Pit

AllysonRating, 5 stars6 days 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 favorite
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 favorite
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

Top guest favorite
Cottage in Guilford
4.94 out of 5 average rating, 268 reviews

The Cottage at Indian Cove

ChristineRating, 5 stars4 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 favorite
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 favorite
Cottage in Milford
4.95 out of 5 average rating, 102 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 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.
Guest favorite
Cottage in Milford
4.95 out of 5 average rating, 321 reviews

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

AlyssaRating, 5 stars1 week 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 favorite
Cottage in Cornwall
4.93 out of 5 average rating, 153 reviews

Newly Built Cottage in Housatonic Valley

AnthonyRating, 5 stars2 weeks ago
Our third time here. Great stay, so cozy and full of light. Pooch friendly. Perfect location for hiking and restaurants too.
Top guest favorite
Cottage in Groton
4.95 out of 5 average rating, 211 reviews

EASY BEAT

RossRating, 5 stars1 day ago
Great place for my wife and I to stay while visiting our son. Super fun place with everything we needed. Close to the water and several historical sites. Easy drive to New London and Mystic. Would definitely recommend.
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.

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 East Hampton
4.86 out of 5 average rating, 37 reviews

Charming 3 bedroom cottage on Lake Pocotopaug

BobRating, 5 stars7 months ago
Very nice lake house with great Autumn views
Guest favorite
Cottage in Coventry
4.92 out of 5 average rating, 37 reviews

Lake Getaway at Coventry Lake! close to Uconn

JamesRating, 5 stars1 week ago
Julie's cottage is so nice! The drive to and from is beautiful and peaceful with woodland scenes everywhere. The cottage is fully stocked in the kitchen, bath, and laundry. There are plenty of extra blankets and pillows. It's all here! Julie is also very responsive and helpful when needed. This is the best in the area! Once you stay here, other AIRBNB locations seem to be lacking.
Top guest favorite
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 favorite
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 favorite
Cottage in Madison
4.94 out of 5 average rating, 33 reviews

Adorable cottage close to beaches and downtown

YaoRating, 5 stars2 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 favorite
Cottage in Lyme
5 out of 5 average rating, 18 reviews

Bucolic Farm On A Country Road

K.K.Rating, 5 stars5 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!

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