Middlesex County Holiday Rentals from €199: Search Short-Term Rentals

A coastal town with a lighthouse, houses, and a river.

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Our top choices for Middlesex County holiday rentals

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Frank

includes taxes & fees

10 Sept - 11 Sept

1 bedroom, desk, iron/ironing board, travel cot

2. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

includes taxes & fees

8 Sept - 9 Sept

Smart TV, fireplace, books, music library

3. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Haddam

Kate F.

includes taxes & fees

24 Aug - 25 Aug

4. #24 Serenity A Lakefront Cottage Retreat

Middletown

Rodrigo C.

5. 2BR Apartment Near Wesleyan 102

Washington Street Historic District

DANIEL M.

Coffee/tea maker, fridge, microwave, oven

6. 2BR Apartment Near Wesleyan 301

Washington Street Historic District

Joanne L.

7. Lakeview Carriage House with Spectacular Sunset Views

Lake Pocotopaug

Jennifer J.

includes taxes & fees

7 Sept - 8 Sept

8. Walk To Goodspeed Opera House!

East Haddam

Amber J.

includes taxes & fees

10 Sept - 11 Sept

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Top Middlesex County Hotel Reviews

Omni New Haven Hotel at Yale

10/10 Excellent

"Some of the staff in the front office and f&b. Eugene at the door and Trisha at the desk ate amazing. Theirs another name in the restaurant, It'll come to me on my next review."

The Capitol Hotel

8/10 Good

"An Honest Review from Someone Who Travels for Work I read the previous reviews before my stay, and honestly, I was a little terrified when my assistant booked this property for my 4-day work trip. After staying here, I wanted to share my own honest experience. Location: The location is excellent. The hotel is directly across from the beautiful Bushnell Park and only about a 5-minute walk from downtown Hartford. Hotel: Yes, the hotel is older and definitely has an outdated feel. You may notice an old-carpet smell, but considering the age of the building, it wasn't a major issue for me. Room: I stayed in a Queen room, and overall, it was clean and well maintained. My only complaint was the lighting. The room was fairly dark, and I had to rely mostly on the lamps on the nightstands. Bathroom: The bathroom is also older and could definitely use an upgrade. However, it was clean and perfectly fine for taking a shower. One thing I did find inconvenient was that there were no electrical outlets in the bathroom. Breakfast: DELICIOUS! Definitely one of the highlights of my stay. Staff: The staff was welcoming, friendly, and attentive throughout my stay. Overall: Was it a modern, luxury hotel? No. Is the property showing its age? Absolutely. But it was clean, comfortable, conveniently located, and the staff was great. Based on some of the previous reviews, I expected much worse. My experience was actually quite positive, especially for a work trip."

Two Trees Inn

10/10 Excellent

"Beautiful property, large rooms lots of space. Very clean. Pool was good and it has a hot tub as well. Breakfast was pretty good, need more options. Had dinner there, everything we ordered was top notch, (hoping they add a few more items) and the staff was extremely kind, attentive and helpful with fun things to do in the area. Honestly wish I would have stayed another night. Already thinking about the next time I visit."

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Holiday Homes in Middlesex County

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Look no further and take a look at our great range of rental properties in Middlesex County!

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Middlesex County holiday rentals

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2. 1-bedroom cottage with Grove Beach 🏖️ access.

3. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown