Middletown Cottages

A forested landscape with a winding dirt road and power lines.

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Our top choices for Middletown cottages

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

1. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

includes taxes & fees

21 Oct - 22 Oct

A two-story house with a porch, a mailbox, and a lawn.

2. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

Samantha D.

includes taxes & fees

20 Oct - 21 Oct

A white cottage with a front door, a garage, and a small porch with a potted plant.

3. The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton

Mary S.

includes taxes & fees

20 Oct - 21 Oct

A dining area with a round wooden table surrounded by six white chairs with dark cushions. A potted plant with green foliage and pink flowers is placed in the center.

4. Privet Farm cottage with AC and Deck in charming Salem Connecticut

Salem

Kellie

includes taxes & fees

14 Oct - 15 Oct

A two-story brick house with a white garage door, surrounded by a well-maintained lawn and a tree.

5. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Oakville

includes taxes & fees

14 Oct - 15 Oct

A living room with a sofa, armchair, coffee table, and a television.

6. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Center

includes taxes & fees

14 Oct - 15 Oct

A house with a porch and a small shed in the background.

7. Waterfront Lake Cottage - Lake Access -Kayaks

Avon

includes taxes & fees

1 Nov - 2 Nov

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Top Middletown Hotel Reviews

Holiday Inn Express Southington by IHG

8/10 Good

"A fairly clean hotel with very nice staff! The only thing that bothered us was the constant smell of weed/marijuana every day we were there."

New Haven Hotel

8/10 Good

"Very straightforward business class hotel. Clean, efficient, operates well. Parking across the street with key card you need to pick up at check-in. Decent amenities, very on-par with what you would expect for a hotel in this category. We chose it for location and for room setup -- there is a pull-out sofa in the room with a king sized bed."

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