Vacation rentals in Middlesex County

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Top-rated vacation rentals in Middlesex County

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Guest favorite

A private deck features a railing overlooking calm waters, framed by green grass and bordered by trees. Sunlight reflects off the water under a clear blue sky, creating a peaceful view of the surrounding shoreline and distant houses.

Guesthouse in Essex

4.82 out of 5 average rating, 28 reviews

Privateers Boathouse (Village Waterfront)

NealRating, 5 stars4 months ago

We always visit Essex once a year and this is out first time that we stayed elsewhere besides a hotel. A perfect place in a perfect location. Loved everything about it and Annie and this is our new Essex retreat for the years to come. Could not be more happy with all aspects of our stay.

Guest favorite

A scenic beach scene captures individuals enjoying a relaxing day by the water. Sun loungers are positioned in the soft sand, with gentle waves lapping at the shore and a vibrant blue sky filled with fluffy white clouds.

Cottage in Guilford

4.93 out of 5 average rating, 267 reviews

Charm + location. Walk to beach, town, & harbor.

AllisonRating, 5 stars1 month ago

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!

Top guest favorite

Home in Old Saybrook

5 out of 5 average rating, 49 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

DavidRating, 5 stars1 month ago

What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.

Guest favorite

A screened-in porch offers views of the water and sandy beach, with natural light filtering through large windows. A patterned rug covers the floor, while a white wicker chair invites relaxation. The lush green lawn and shoreline are visible outside.

Cottage in Guilford

4.95 out of 5 average rating, 80 reviews

Direct Shoreline Long Island Sound Waterfront

ThomasRating, 5 stars7 months ago

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Guest favorite

A charming home showcases a private deck adorned with planters and ample seating under a striped umbrella. Lush greenery surrounds the area, complementing the shingle-style exterior, and large windows invite natural light into the space.

Home in Westbrook

4.93 out of 5 average rating, 42 reviews

Private vacation home, close to beach

JaniceRating, 5 stars5 months ago

We loved our stay in Westbrook! Mia's lovely home exceeded our expectations in terms of decor, furnishings, cleanliness, comfortable beds, and well-stocked kitchen and bath ... all in a quiet and private setting. The house was especially well-situated for us. We had tickets for a special theater performance at Gillette Castle one evening, and then had to be in New Haven on the next day. All were easy drives. And, there are amazing fine dining options nearby. We'll definitely try to book this wonderful place any time we have events in the area. Thank you, Mia, for a magical Autumn weekend in Connecticut!

Top guest favorite

A serene outdoor seating area is displayed, featuring cushioned wicker furniture arranged around a light-colored table. The lush green lawn leads to calm waterfront views, with distant trees and a dock visible across the water under a clear blue sky.

Cottage in Old Saybrook

5 out of 5 average rating, 98 reviews

Cozy Waterfront Retreat

AaronRating, 5 stars1 month ago

We had a chance to stay at the beautiful beachfront home, and it was amazing. Waking up to Eastern sunrises each morning and dining in nearby Kennebunkport was amazing. The hosts were very responsive and easy to communicate with. I highly recommend!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Middlesex County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Middlesex County

Guest favorite

A lakeside view of a two-story home with a spacious deck that overlooks the water. A well-maintained yard is visible, featuring outdoor seating and greenery. A dock extends into the lake, inviting boat access. The home is surrounded by trees, providing a serene atmosphere.

Home in East Hampton

4.87 out of 5 average rating, 97 reviews

Beautiful Lake House on Lake Pocotopaug

StephenRating, 5 stars4 months ago

Great place to stay! My family and I enjoyed our stay during the Holidays! Courtney was a great host!

Top guest favorite

An aerial view of the estate highlights a spacious property set amidst lush greenery. The main building reveals a large back terrace, while a separate structure stands nearby. Two paddle boards rest on the grass beside a well-maintained lawn, providing a glimpse of outdoor activities.

Home in Old Lyme

4.98 out of 5 average rating, 55 reviews

Relax & Rejuvenate in this 1920s Riverfront Estate

JasonRating, 5 stars6 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

A comfortable living area features a cozy seating arrangement with a blue sofa and an inviting armchair, set against a rustic stone fireplace. A warm light emanates from above, illuminating the wood-paneled ceiling and vibrant area rug. Large windows allow natural light to fill the space.

Cottage in Hebron

4.89 out of 5 average rating, 134 reviews

Welcome to The Holly at Amston Lake

MasonRating, 5 stars2 weeks ago

This place is the perfect getaway location, especially for a quiet relaxing weekend. Great host who was super responsive and flexible with me trying to check in early.

Guest favorite

The entrance features a welcoming door with an emblem above. A wooden deck with a table and chairs is visible, offering a casual outdoor seating area. The surrounding landscape shows a gravel area and additional structures in the distance, suggesting a beach community setting.

Home in Westbrook

4.82 out of 5 average rating, 11 reviews

Beachside @ 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.

Guest favorite

Two adirondack chairs are positioned on grassy land, facing a serene lake. A wooden dock extends into the water, with a kayak and inflatable paddleboard anchored nearby. A small fire pit sits between the chairs, surrounded by calm reflections of trees along the shore.

Home in East Haddam

4.95 out of 5 average rating, 204 reviews

Romantic Getaway at The Lake!

HamzaRating, 5 stars3 days ago

We loved our stay. Loved the view, the fire pit, the hot tub, and everything else that the place had to offer. Thanks Tim!

Guest favorite

A serene lakeside view is captured at sunset, showcasing vibrant hues of orange and purple reflecting on the water's surface. Silhouettes of trees frame the scene, while a small dock with steps leads to the water, accompanied by several outdoor chairs arranged for relaxation.

Cottage in Lebanon

4.97 out of 5 average rating, 38 reviews

"The Napping House". Lake front, kayaks, fire pit.

KayRating, 5 stars8 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

A rustic log cabin is surrounded by lush greenery and tall trees, creating a serene atmosphere. Large windows provide views of the lake, enhancing the connection between the indoor and outdoor spaces. The inviting front porch offers a welcoming entry to the home.

Cabin in East Hampton

4.79 out of 5 average rating, 14 reviews

Spacious family lakeside homestead

PamRating, 5 stars6 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

A clear blue pool glimmers under sunlight, surrounded by a sleek wooden deck. Four lounge chairs are positioned for relaxation, accompanied by two round planters filled with vibrant greenery. A white safety fence outlines the pool area, enhancing the tranquil outdoor setting.

Home in Middletown

4.95 out of 5 average rating, 40 reviews

Hot 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!

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Vacation rentals in Middlesex County

Top-rated vacation rentals in Middlesex County

Vacation rentals for every style

Popular amenities for Middlesex County vacation rentals

Other great vacation rentals in Middlesex County

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