
Vacation rentals in Middlesex County
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Top-rated vacation rentals in Middlesex County
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Other great vacation rentals in Middlesex County
Guest favorite

Home in Colchester
4.78 out of 5 average rating, 27 reviewsHilltop Hideaway
BreRating, 5 stars2 months ago
Our stay at this hidden gem was nothing short of magical! Nestled away from the hustle and bustle, it provided the perfect escape we were looking for. The cozy interiors, thoughtful amenities, and stunning views made it feel like a home away from home. The host was incredibly welcoming and attentive, ensuring we had everything we needed for a comfortable stay. Whether you're looking for a peaceful retreat with family or a romantic getaway, this hideaway is the perfect choice. We can't wait to return!
Top guest favorite

Home in Old Lyme
4.98 out of 5 average rating, 55 reviewsRelax & Rejuvenate in this 1920s Riverfront Estate
JasonRating, 5 stars5 months ago
My family and I have rented several homes for vacation over the years, but this home is truly a special place. The property is gorgeous! The views are amazing, and we enjoyed spending many hours taking it all in. Lots of wildlife to observe and the private hiking trail was a great bonus. The house itself was wonderful…a unique mix of history, art, music, and modern technology. Everything was high-end and excellent quality. The bed in the master bedroom was the most comfortable we have ever slept in away from home. The house was extremely clean and had everything you would ever need and plenty of it. We have never seen a vacation house with so many extra linens, toilet paper, Kleenex, coffee, etc. We were so impressed! Hector is an exceptional host, friendly and responsive. His home is incredibly peaceful, a true sanctuary. We are so very grateful that we chose this house for our family vacation. Thank you, Hector!
Guest favorite

Cottage in Hebron
4.89 out of 5 average rating, 131 reviewsWelcome to The Holly at Amston Lake
IsaiRating, 5 stars5 days ago
The Holly was such a great stay!! I wanted a spot to rest and recharge and this cottage on the lake was the perfect place for me. Jasmine went above and beyond to communicate prior to my arrival and very helpful in providing recommendations for local spots. As I was heading to my final day, Jasmine continued her proactive communication with checkout details and was available for any questions I had. Her home was lovely and super comfy which made me feel right at home. Looking forward to explore more of this area of CT and my return to The Holly. 10/10 recommend!!
Guest favorite

Home in Westbrook
4.82 out of 5 average rating, 11 reviewsBeachside @ 455 Seaside
AliciaRating, 5 stars4 months ago
My family had a wonderful stay at Jason’s beautiful, clean, and cozy home. The location is perfect. We enjoyed the beautiful view of the beach during sunrise. Jason was very responsive! We would definitely love to stay here again.
Top guest favorite

Home in Clinton
5 out of 5 average rating, 24 reviewsSoundscape Beachfront House!
TerrenceRating, 5 stars3 months ago
Victor's was an exceptional host who went above and beyond to ensure we enjoyed our stay - and was very attentive to all the details. And his home was lovely - right on the LI Sound. Great place to stay and unwind wiht family!
Guest favorite

Cottage in Lebanon
4.97 out of 5 average rating, 38 reviews"The Napping House". Lake front, kayaks, fire pit.
KatherineRating, 5 stars7 months ago
This is our second stay at Scott’s place, we enjoyed it so much we came back this year, and hope to go back next year. My husband and I enjoyed the many moods. Of the lake. He is an avid fisherman and I am a swimmer the whole Connecticut Valley region is a favorite of ours.
Guest favorite

Cabin in East Hampton
4.79 out of 5 average rating, 14 reviewsSpacious family lakeside homestead
PamRating, 5 stars5 months ago
Kevin was very communicative from the start. He met me at the door and gave an accurate lay of the land. The cabin was the perfect rustic place for our trip. The lake view was amazing and waking up to a beautiful sunrise and having coffee on the deck was an amazing way to start each day.
Guest favorite

Home in Middletown
4.95 out of 5 average rating, 40 reviewsHot Tub and pool Home away from home
KristenRating, 5 stars3 months ago
Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!
Destinations to explore
- Rentals with beach access Middlesex County
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- Rentals with a fireplace Middlesex County
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- Rentals with a patio Middlesex County
- Bed and breakfasts Middlesex County
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- Rentals with lake access Middlesex County
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- Rentals with a kayak Middlesex County
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Clinton Town Beach
- Shennecossett Beach
- Six Flags New England
- Cooper's Beach, Southampton
- Woodmont Beach
- Horton Lane Beach
- Mystic Seaport Museum
- South Pine Creek Beach
- Sasco Hill Beach
- Wildemere Beach
- Morningside Beach
- Anchor Beach
- Fenway Beach
- East Beach
- Money Beach
- Jennings Beach
- Fairfield Public Beach
- Long Beach