
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

Cozy Lakefront Retreat | New Backyard & Hot Tub
Our family of five loved staying at Yoka and Val's place. The location is very quiet with a peaceful pond across the street. The house itself is very clean and comfortable with everything you need - towels, soap, shampoo, conditioner, coffee and spices - easily available. The beds were also very comfortable. The best part, of course, was the private hot tub in the back yard. It was set in a canopy for extra privacy and wind protection. We loved it. We would definitely stay here again if in the area.

Private Beach Cottage
This well-appointed space is perfect for two people. Old Lyme is justly famous for its Florence Griswold Museum, as well as one of the better historic main street walking tours. (Currently, there's an exhibit at the museum about Old Lyme's slave-owning past.) And, then, of course, there's the ocean. Remember to ask your hosts about their beach parking pass. P.S. You may also need to bring your own coffee for the drip system.

“The Lil Nauti” Newly Updated! 1 block to 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 Lakefront Cottage w/Swim Spa & Firepit
Just as listed...small cottage by the water and the view was stunning! I liked relaxing in the swim spa or by the calming lights and sounds of the fake electric fire-- definite cozy vibes! The kitchen is clean and well stocked with utensils etc. Feyza was great about checking in. Thanks!
Pet-friendly cottage rentals

Welcome to The Holly at Amston Lake
Such a great stay! The area is beautiful, and you can see the water right from the front deck. The Airbnb itself is so cute, with great little touches, like a coffee bar, fire pit, and great views. It was a really peaceful stay, and our pups loved it too.

Game Room-Mins to Beach&Boardwalk-Walk to Marinas
Erin’s place was perfect for our family weekend away! It was incredibly clean, stocked with everything we needed, and was a lovely space. The game room was a huge bonus, our son absolutely loved playing the arcade games all weekend :) Erin is a great host. Would definitely stay here again!

Sun Filled Cottage
My husband and I stayed at the cottage for 3 months and enjoyed our time very much. We were very happy from every perspective: The cottage had all the equipment we needed and wished for. We sometimes used the fireplace and loved the bed/couch. The cottage is perfect to rest and focus. We enjoyed to have so much nature around us. We took a walk in the close park with a lake almost every day. We liked to live at a small farm with dogs, chicken and goose. Debbie and Kirk were always there when we needed them and also made us internationals feel welcome. They explained and helped us proactively e.g. changed regional weather circumstances. We also regularly got eggs from the chicken what was always a nice surprise. Communication/ interactions were always easy and friendly. I recommended my work to plan future stays for assignments in this Airbnb. In our opinion it is better than a hotel: Very comfortable, cozy, close to nature and a special American experience. Thanks a lot Debbie and Kirk

In-law apartment in Farmington River Cottage
Great place great hospitality really loved the stay she was really nice I would 100% book again she is just the most sweetest person I’ve met !

Charm + location. Walk to beach, town, & harbor.
This was my fifth stay in Jeanne's wonderful cottage! The cottage gets better and better each time I visit: a newly renovated bathroom, redecoration in lighter/brighter colors, etc. The home is extremely well stocked - every kitchen item you might need (including loads of glasses/plates/silverware, pots/pans, etc.), thick towels, extra blankets and throws, and lots of cleaning and paper products. There are plenty of cozy places to sit and relax, both indoors and out. The best thing of all is Jeanne herself, who is without a doubt the most generous host I've encountered on AirBnB. She is friendly, communicates proactively, and is quick to respond to any issues/questions. She truly opens her home to her guests, encouraging visitors to use the space fully and to make themselves at home. The cottage is an easy walk to the beach ane/or to town and is lovely, homey, and peaceful. I'll definitely return!

Serene Waterfront Cottage
As always, we love our stay at the cottage. It’s becoming our home away from home when visiting our son. Thanks for all our goodies! Always a great surprise! Have a wonderful Christmas. We’ll see you next year I hope.

The Little Red Schoolhouse ~ Circa 1877
This is a lovely historic building in peaceful surroundings. It's spacious and clean inside, with comfortable beds and couches. If you have problems with steep stairs it might be tricky, but there are two handrails to help. The only bathroom is downstairs - something to keep in mind if you need to get up at night. The host was very responsive about some minor repair issues we reported. I'd be happy to stay there again!

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly
We had nice weekend at the cozy cottage. We loved that it was pet friendly and a short walk to the beach. Cameron was very friendly and responsive. She offered great suggestions for food and activities.
Private cottage rentals

Beachfront Cottage Serene Private Beach, Kayaks
We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.

Waterfront Beach Cottage in Connecticut
Eglantine was a very responsive host! She answered immediately with whatever question I had and also very helpful. The binder provided also helped out a ton. There was a slight hiccup with the refrigerator turning off while we were away and we had to throw away some of our perishables because the internal temp of the fridge reach 84 degrees, but Eglantine responded right away when we contacted her about the issue.

Lake Getaway at Coventry Lake! close to Uconn
This is a super cute cottage that is well decorated and has a fully stocked kitchen. Everything felt new. It was a cozy place to watch movies on cold nights with a gas fireplace. About a 12 min (pretty) drive to UConn. Julie was a wonderful hostess—so responsive. I highly recommend this place!

Cheerful 2 bedroom cottage on beach
This house is absolutely perfect. It's clean, charming, has everything you need. The beautiful back yard has plenty of space and good stuff for kids to play with. Also, it's about a 30 second walk to the beach... neighbors are out on their patch of beach but yours is yours to yourself. It's perfect. We cannot wait to come back.

Adorable cottage close to beaches and downtown
This is by far one of the best and cutest airbnbs I’ve stayed in up until now! My friends and I stayed here for my bachelorette weekend and absolutely loved it. We’d definitely recommend it and stay here again if we could! The hosts were so sweet and friendly. They left us wine and rose and gave us an extended checkout. Their place was so cozy and clean too!

Seasonal Beach Cottage
What a find!! The location is wonderful and so is the cottage! So close to the beach. It’s clean and spacious. I can’t wait to bring the whole family for a week here. I highly recommend this home for anyone looking for a great escape.

Shalom Cottage with beach rights.
Raj’s place is a cute little cottage tucked back off the main road. It was super comfortable and clean. The inside is nice decorated and a bit of a surprise from the plain exterior. Raj is in the process of renovating an old motel and the cottage is the first to be completed- it will all be great when done but not what you might expect now at first glance today. Raj is rightly proud of the work being done. He is a super communicated with lots of area suggestions and helpful hints. The cottage had fresh flowers, fruit, and even cloth napkins. Really everything we needed for a comfortable overnight stay.

Ret's Coastal Cottage w/Private Association beach
Thank you !! We enjoyed our stay. The home is lovely and the area was so convenient to all ! The airport is 7 minutes away. Def would stay here again. Thanks again
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Six Flags New England
- Quotonset Beach
- Shinnecock Hills Golf Club
- Giants Neck Beach
- Woodmont Beach
- Walnut Public Beach
- TPC River Highlands
- Clinton Town Beach
- Seaside Beach
- Jennings Beach
- Amagansett Beach
- Thunder Ridge Ski Area
- Attawan Beach
- Shennecossett Beach
- Anchor Beach
- Long Island Aquarium
- Clinton Beach
- Groton Long Point Main Beach
- Mohawk Mountain Ski Area