House vacation rentals in Middlesex County

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Popular amenities for Middlesex County house rentals

House rentals with a pool

Guest favorite

Home in East Hampton

4.95 out of 5 average rating, 60 reviews

Country getaway - huge yard, pool

KetwlyRating, 5 stars2 months ago
Our stay was wonderful. Lena is the perfect host. We are already talking about going back next fall!
Guest favorite

Home in Old Saybrook

5 out of 5 average rating, 13 reviews

Beautiful Shoreline home in parklike setting

NishaRating, 5 stars4 months ago
Patricia was the perfect host. Her home is beautiful and peaceful, perfect for a family holiday. We loved spending time in the pool and it’s a perfect location to explore the CT coast. We would definitely be back. Many thanks Patricia.

Home in Old Lyme

4.7 out of 5 average rating, 10 reviews

Gorgeous 1700s Home Sleeps 10, 3 bath, Pool

MarcellaRating, 5 stars4 months ago
This was a wonderful summer stay for our large family with plenty of rooms/beds and a large yard with a pool (which included plenty of fun floaties for the children). Our check-in contact was super responsive and made herself available to help us check in (even though we got in pretty late) and gave us a tour of the house and its amenities. Our stay included someone nearby to maintain the yard/pool and he even provided some fresh produce for us from his garden. We hope to be back to have a chance to further explore the neighborhood and town.
Guest favorite

Home in Madison

4.93 out of 5 average rating, 15 reviews

Fabulous pool in beach town!

DovidRating, 5 stars3 months ago
We took the house for a family getaway, and it far beyond surpassed our expectations. From the cleanliness of the home, to the beauty and utility of the pool. There was an abundance of all things you can expect to find in a home, e.g. the bathrooms were stocked with an abundance of name brand shampoos and soaps. We enjoyed the beautiful coastline that was in close proximity to house. And we spent hours at the pool on a daily basis, it was very private. Cindy was responsive to our every need and query. She even came by a couple of times to help us out with some issues, she went beyond her call of duty. All this she did graciously, as if it’s not even a bother. She is a true super host.

Home in East Hampton

5 out of 5 average rating, 4 reviews

Direct riverfront luxury home!

AshleyRating, 5 stars4 months ago
The house accommodated our group so perfectly! The house was just as described and the property and area were absolutely beautiful! Theresa was also very friendly and communicative. We would definitely stay here again. Thanks for making our stay a memorable one!

Home in Clinton

4.96 out of 5 average rating, 28 reviews

NEW! 5-bedroom historic cottage, near beach

BritanyRating, 5 stars1 month ago
Melina was a great host and this property exceeded our expectations. It was nicely decorated, clean, cozy, and met our needs. The historic home had plenty of charm, and it was clean. Compared to staying in a local hotel, this was a much better choice. It was close to the Clinton outlets and restaurants, but in a family-friendly neighborhood just a few minutes away. The only surprise was that the 2nd floor ceilings are low, and we had to duck to use the bathroom and smaller bedroom. If you're under 5'10", it won't be a problem for you, but we are taller than that. However, I would still rent the house again. All of the beds were comfortable, there were towels, shampoo, conditioner, soap, a hair dryer, etc. ready for guests. I fully recommend it and would absolutely stay here again.

Home in Killingworth

4.75 out of 5 average rating, 4 reviews

Quiet Connecticut Retreat w/ Pool, Deck & Fire Pit

EmiliaRating, 5 stars6 months ago
We had an amazing time at the house. The pool was so big and the kids enjoyed themselves. The house was beautiful so much space. Our family will be coming back and recommend to anyone to stay.
Guest favorite

Home in Middletown

4.95 out of 5 average rating, 39 reviews

Hot Tub and pool Home away from home

ChadRating, 5 stars2 months ago
Beautiful and clean house with top of the line amenities and many fun things to keep our friends and family entertained through out our stay. Would definitely recommend and rent the house again when we are in the area. Thx

Weekly house rentals

Superhost

Home in Guilford

4.82 out of 5 average rating, 28 reviews

Guilford Home self check-in & off street parking

martaRating, 5 stars3 months ago
In town for a reunion over the long holiday weekend and Tricia’s cottage was available and perfectly located within 10-15 min of every place I needed to be. So welcoming and easy, comfortable and tastefully decorated. Every amenity I could have wanted was provided. I felt safe and was able to relax and enjoy my stay. Bonus, Tricia offered a late checkout, giving me extra time to soak up the trip back home after so many years. Would definitely stay again!
Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 266 reviews

Modern Luxurious CT Country Home

AimeeRating, 5 stars2 weeks ago
Our Thanksgiving weekend at Christoph's Airbnb was truly delightful! The house is stunning and served as a perfect getaway from the city. The scenic surroundings added to the charm, and the home was thoughtfully equipped with everything we needed for a relaxing and enjoyable stay. It was spotless, comfortable, and exceeded all our expectations. Christoph was an attentive and welcoming host, making the experience even better. Highly recommend this beautiful retreat. Thank you, Christoph, for a memorable stay!
Superhost

Home in Westbrook

4.85 out of 5 average rating, 182 reviews

Family-Friendly Cottage by The Shore

SkipRating, 5 stars1 week ago
Marie's place is cute, comfortable and conveniently located. We will definitely consider going back.
Guest favorite

Home in Middletown

4.88 out of 5 average rating, 294 reviews

Historic Greek Revival Brick Home

JoshRating, 5 stars1 month ago
Another wonderful stay at Bill & Megan's! We try to stay at one of their apartments whenever we visit our daughter at Wesleyan. And this is our favorite unit in the house. But no matter which unit you're in, the location cannot be beat. And Bill and Megan are great hosts! Don't give it a second thought!
Guest favorite

Home in Madison

5 out of 5 average rating, 22 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

JenniferRating, 5 stars1 month ago
The house was gorgeous! Very spacious with beautiful design elements. Everything was extremely clean. The host had great communication and was very friendly. My family and I were very satisfied with our stay!
Guest favorite

Home in Essex

4.96 out of 5 average rating, 69 reviews

4-Bedroom Farmhouse *Comfort and Privacy*

KellyRating, 5 stars5 days ago
It was our third time staying at WitchWay and was just as amazing as ever. The house is always spotless and cozy and Aude is SO responsive-leading up to the visit and also during the stay. My family and I look forward to our annual visit to Essex and love our tradition staying at the Farm!
Guest favorite

Home in Madison

4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars2 months ago
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.
Superhost

Home in Westbrook

5 out of 5 average rating, 3 reviews

Sunset Skies 2nd Fl | redone+walk to Water’s Edge

CarrieRating, 5 stars1 month ago
Great stay! One of the best AirBnB accomodations we have visited; everything was perfect! The location is ideal to walk to Water's Edge Resort or downtown Westbrook, very close to the beach. The stay was beautiful with brand new amenities, exactly as described. Kelly was very responsive, kind and helpful with any questions we had. We cannot wait to stay here again for a future stay.

Private house rentals

Superhost

Home in Guilford

4.87 out of 5 average rating, 47 reviews

The Davis House

KimberlyRating, 5 stars1 month ago
This was our second stay at Sharon‘s house. The house was spotless and cozy. Plenty of room.The beds were comfortable. Sharon is outgoing and friendly. We will be back next year.
Guest favorite

Home in Haddam

4.97 out of 5 average rating, 77 reviews

Autumn at The Haddam House

ChristopherRating, 5 stars3 months ago
I loved my stay at The Haddam House! It was cozy and tidy and just as described. And the waterfront bar/dock area was amazing. I would definitely come back again.
Guest favorite

Home in Clinton

4.96 out of 5 average rating, 25 reviews

Zaku’s Lake House

KathleenRating, 5 stars4 months ago
We had a wonderful stay! This is our second time staying in the home and both times Mariza was accommodating and great to work with. The house is in a great location on the water and is clean and maintained very well. We plan to stay again in the future!
Guest favorite

Home in Guilford

5 out of 5 average rating, 17 reviews

Coast and Country Private Estate

TinaRating, 5 stars3 months ago
What a stunning home in a beautiful and peaceful location in Guilford, CT. My 2 sisters and I brought our 86-year-old Mom to this home for a long weekend getaway. It was perfect. The decor is lovely and interesting. The screened sun porch is great - we played games there. Fully stocked kitchen is an understatement. In fact, all items needed were available in abundance. The back deck is great as well overlooking the back yard and pond. We used the gas fireplace at night. I celebrated a milestone birthday and invited a few other family members and Susanne was very accommodating. If you are looking for a fabulous place to get away in any season - this is the place!
Guest favorite

Home in Essex

4.94 out of 5 average rating, 18 reviews

Hyde House-A classic New England cape.

AndreRating, 5 stars2 months ago
My friends and I had a lovely stay at your home in Essex this past weekend. The house was very clean and comfortable and in a very pleasant neighborhood. It was well appointed and very homey. Thank you!
Superhost

Home in Old Saybrook

5 out of 5 average rating, 3 reviews

Fenwood Coastal Getaway Private Beach Access

MichelleRating, 5 stars3 months ago
Jasons house was a perfect, comfortable stay for our group attending a wedding. It is a block from the water and gives you access to the private beach. The beds and couch were very comfortable and the space was clean.
Guest favorite

Home in Clinton

4.79 out of 5 average rating, 43 reviews

LONG-TERM Glass House-Fall/Beach 5mins/Ski 25mins

BrianRating, 5 stars1 month ago
Awesome location and home. Enjoyed the long weekend here, will use again if I’m back in the area.
Guest favorite

Home in Guilford

5 out of 5 average rating, 24 reviews

Entire home - Cheerful 4 bedroom on the shoreline.

AshleyRating, 5 stars1 month ago
Beautiful spacious house in an excellent location. Host greeted us upon arrival, which was extra, and appreciated. Very clean uncluttered house- clean linens and towels. Beautiful yard. Walkable neighborhood and proximity to beach and town is ideal. Totally recommend, and we would definitely rent this property again! Fresh dahlias in the kitchen!

Destinations to explore