
Cottage vacation rentals in Middletown
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Top-rated cottage rentals in Middletown
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Popular amenities for Middletown cottage rentals
Cottage rentals with a hot tub

Luxury cottage by the sea with hot tub and pool
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!

The Cottage at Blackberry River Inn
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.

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

Lakefront Summer Escape | Cool Tub | Fire Pit
Absolutely stunning views and peaceful vibes at this sweet cottage!!! Totally exceeded my expectations. Book now or you’ll regret it!!!

Private Beach Cottage
Great communication with host, beach within walking distance was so nice, overall good spot within 30 mins of mystic aquarium and Foxwoods casino

The Lil Nauti Cottage, Steps To Fairfield Beach
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.

Cozy Getaway | Pet Friendly | Litchfield Cty
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

The Cottage at Indian Cove
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!

In-law apartment in Farmington River Cottage
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!

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN
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! :)

Charm + location. Walk to beach, town, & harbor.
It was so comfortable and peaceful. We had a great time exploring nearby beaches and hikes. We would definitely stay there again.

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

Newly Built Cottage in Housatonic Valley
Our third time here. Great stay, so cozy and full of light. Pooch friendly. Perfect location for hiking and restaurants too.

EASY BEAT
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.

Cozy Waterfront Retreat
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

Churchill Cottage
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.

Charming 3 bedroom cottage on Lake Pocotopaug
Very nice lake house with great Autumn views

Lake Getaway at Coventry Lake! close to Uconn
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.

New & Beautiful Lake cottage
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.

The Treehouse at Lake Hayward
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!

Cozy Lakefront Cottage Perfect for Families
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.

Adorable cottage close to beaches and downtown
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!

Bucolic Farm On A Country Road
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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- Beach
- Fairfield Beach
- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Ocean Beach Park
- Thunder Ridge Ski Area
- Woodmont Beach
- Amagansett Beach
- Seaside Beach
- Quotonset Beach
- Bushnell Park
- Jennings Beach
- Silver Sands Beach
- South Jamesport Beach
- Groton Long Point Main Beach
- Clinton Town Beach
- Sherwood Island State Park
- Bayview Beach
- Cedar Beach