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

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.

Lakeside cottage with beautiful views up the lake!
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.

Lovely 2 BR Beach House No. Shore
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 !

Lakefront Summer Getaway | 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.

1 Bed Pond Cottage w/ Pool/Hot tub/Sauna access
Sarah's place is an absolute gem! From the beautiful views and serene atmosphere to the cozy cottage and amenities, our experience was truly special. While the weather didn't cooperate for us to use the pool, and the hot tub wasn’t available, we made the most of the sauna and spent time enjoying the rest of the property. The lake views and peaceful surroundings, made our stay unforgettable. Sarah, Anya, and the whole family were extremely welcoming and great hosts. They made sure we had everything we needed and were always quick to respond to any questions. The property offers everything you need for a relaxing getaway, and it’s conveniently close to Kent for some great outings to restaurants and shops We highly recommend this spot for anyone looking for a quiet retreat with nature and serenity. We’ll definitely be back!

Cozy Getaway | Pet Friendly | Litchfield Cty
great time as always!
Pet-friendly cottage rentals

Foxfire Hill: A Bit of Luxury in the Countryside
This is our second time staying at Foxfire Hill, and it was wonderful to see the gardens in their glory. Great and responsive hosts. I’m sure we will be back again.

Mystic, CT Pet-Friendly Cottage with Hiking Trails
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!

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! :)

Montauk Oceanview
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!

Stuart Cottage/Minutes to Mohawk Ski Area
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.

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.

1920’s charming dollhouse near South Cove
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.

Cozy Home In Short Beach Community
My wife and I had a wonderful stay at the cottage. It was extremely cozy and in a beautiful location right near a quiet beach. It’s also very close to New Haven, making trips to and from very easy. Would definitely stay here again!
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.

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.

Waterfront Joshua Cove Cottage with private beach.
Our 2 day stay at the cottage was just what we’d hoped for our wedding weekend! Annalisa was so responsive and accommodating. A wonderful host, such wonderful hospitality and an amazingly stunning private retreat! Would definitely return!

Enchanted Cottage on the Marsh, walk to beach
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

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!

The Carriage House
My second stay here - love this little town and the beauty surrounding it! Kristen’s place is such a great location on lovely, woodsy street, yet within quick access to the Farmington Trail and riverwalk, the town of Collinsville and many other beautiful locations. Love all the windows - makes you feel like you’re up in the trees! Big, comfortable bed as well, which is appreciated after an active day! Thanks, Kristen!
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Six Flags New England
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Seaside Beach
- Blue Shutters Beach
- Quotonset Beach
- Ninigret Beach
- Bushnell Park
- Jennings Beach
- Silver Sands Beach
- South Jamesport Beach
- Groton Long Point Main Beach