House holiday rentals in Middlesex County

Find and book unique houses on Airbnb

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Popular amenities for Middlesex County house rentals

House rentals with a pool

Guest favourite
Home in East Hampton
4.95 out of 5 average rating, 60 reviews

Country getaway - huge yard, pool

KetwlyRating, 5 stars4 months ago
Our stay was wonderful. Lena is the perfect host. We are already talking about going back next fall!
Guest favourite
Home in Old Saybrook
5 out of 5 average rating, 13 reviews

Beautiful Shoreline home in parklike setting

NishaRating, 5 stars6 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.
Guest favourite
Home in Madison
4.93 out of 5 average rating, 15 reviews

Fabulous pool in beach town!

DovidRating, 5 stars5 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 Killingworth
4.75 out of 5 average rating, 4 reviews

11 Mi to Powder Ridge Mountain: Connecticut Home

EmiliaRating, 5 stars8 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.
Home in Westbrook
4.73 out of 5 average rating, 132 reviews

Secluded Family escape w/ pool & jacuzzi

GaryRating, 5 stars4 months ago
Great getaway ! perfect for a guys vacation. Very private.
Guest favourite
Home in Middletown
4.95 out of 5 average rating, 40 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars1 month 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!
Home in Madison
4.79 out of 5 average rating, 38 reviews

Beautiful 1820 Colonial, Madison, CT

AngieRating, 5 stars8 months ago
My husband and I stayed with our 19-month-old son for three nights and it was a perfect choice! Susan had a toys and books that he loved, as well as a sandbox and pool outside - and the home was stocked with everything we needed for our stay. We used the location as a jumping off point for other activities and then had quiet afternoons at the house while my husband rode his bike (we saw lots of other cyclists!). If you are vegan or vegetarian, check out the Shoreline Diner in Guilford - it was delicious.
Home in East Hampton
4.83 out of 5 average rating, 6 reviews

Country escape w/pool, waterfall - 2h NYC/Boston

TaraRating, 5 stars31 months ago
We had such a wonderful time in this home. We loved the pool and used it everyday. We also loved the outdoor space. Perhaps the outdoor space is understated in the advertisement for the house, it is truly magnificent. The air conditioners worked very well and kept things cool inside even on the especially hot days. Thank you for a wonderful experience!

Weekly house rentals

Guest favourite
Home in Old Lyme
4.94 out of 5 average rating, 268 reviews

Modern Luxurious CT Country Home

AnirudhyaRating, 5 stars4 days ago
Chris was a fantastic host! First of all he was so responsive, always checking in on us everyday, and very helpful and communicative with recommendations and quick answers. Second of all, the property. It is so gorgeous. Definitely worth the price, and maybe even better! We loved our stay, we will definitely be coming back soon. Definitely check it out if you’re considering an Airbnb in the area. 10/10 experience!
Superhost
Home in Westbrook
4.85 out of 5 average rating, 186 reviews

Family-Friendly Cottage by The Shore

ElizabethRating, 5 stars5 days ago
Our little kids loved this family-friendly, cozy home, and Marie was a friendly and responsive host. We visited during cold winter weather, but can tell this would be an awesome spot in warmer weather.
Guest favourite
Home in Middletown
4.88 out of 5 average rating, 298 reviews

Historic Greek Revival Brick Home

CynthiaRating, 5 stars2 weeks ago
What a beautiful place to stay! Filled with charm, beautiful high ceilings, crown molding. The antique mirrors and piano add extra charm! Great space to share with my two sisters, fireplace made it extra cozy. Beds comfortable, lots of gathering places. It snowed while we were there, and the hosts didn't skip a beat, with the walk way shoveled and salted, all the way with a path to the car.
Guest favourite
Home in Old Saybrook
4.94 out of 5 average rating, 16 reviews

Seas the Day at the CT Shoreline

ZackRating, 5 stars4 months ago
Alexandra’s place was a great stay for our weekend get away. Short walk to the beach and near anything else you might need. Alexandra was very responsive and accommodating to any questions we had.
Guest favourite
Home in Madison
5 out of 5 average rating, 25 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

MohitRating, 5 stars5 days ago
We had a very comfortable stay at Sascha's place which was just as described in the listing. It snowed during our stay which made the uphill driveway impossible to navigate. Fortunately, the garage was equipped with shovels and salt which enabled us to clear it. The house was very well equipped, in general, and we were very impressed with the attention to detail. The host was very generous with the check in and check out timings, and was very responsive to all of our messages. We strongly recommend staying here.
Guest favourite
Home in Essex
4.96 out of 5 average rating, 71 reviews

4-Bedroom Farmhouse *Comfort and Privacy*

JenniferRating, 5 stars1 month ago
Our stay at Aude’s place raised the bar for AirBnB stays. It was exactly as pictured in the photos but somehow even more spacious! The kitchen was well supplied, the living areas warm and comfortable, the bathrooms immaculate and the bedrooms cozy. Secluded and private yet close to everything you might want to do.
Guest favourite
Home in Madison
4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars4 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 stars3 months 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
4.88 out of 5 average rating, 48 reviews

The Davis House

WilliamRating, 5 stars1 month ago
Would absolutely book again. We were travelling as a family of four (teenager and an elementary schooler) to visit family in Guilford area. This was a great space for us, three bedrooms and baths, den, sitting room, kitchen, dining area. You could do this as a family of five pretty easily, maybe six if someone sleeps on a couch. There's a back porch we didn't use due to cold weather but I suspect is lovely in summer. The residence is well maintained and tastefully decorated, I suspect some of the wall decorations are at Sharon's store. Wi-fi and TV with tubi subscription, and there were some board games in the closet. Sharon noticed snow in the forecast and salted the driveway and walk before we arrived. We didn't experience any problems per se but Sharon was very responsive when we had questions. We had a really positive experience.
Guest favourite
Home in Clinton
4.96 out of 5 average rating, 25 reviews

Zaku’s Lake House

KathleenRating, 5 stars6 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 favourite
Home in Guilford
5 out of 5 average rating, 18 reviews

Coast and Country Private Estate

AlisonRating, 5 stars4 months ago
We stayed at this property the weekend of our daughter's wedding. Susanne was an absolute gem of a host. She checked in the day of our arrival and departure. The house was beautiful, the property and grounds are secluded, quiet and surrounded by nature. Often times a rental feels just like that, a rental. This, however, was as if we'd been invited to spend the weekend at a good friend's home. I would highly recommend this location.
Superhost
Home in Essex
4.95 out of 5 average rating, 19 reviews

Hyde House-A classic New England cape.

SofiaRating, 5 stars1 month ago
Fred’s house was beautiful! Felt home from the moment we walked in. It was clean and cozy! We enjoyed walking to Essex Village (which is so beautiful and charming) it is a very peaceful place and people around are very kind
Superhost
Home in Old Saybrook
5 out of 5 average rating, 3 reviews

Fenwood Coastal Getaway Private Beach Access

MichelleRating, 5 stars6 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 favourite
Home in Clinton
4.81 out of 5 average rating, 47 reviews

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

SarahRating, 5 stars3 weeks ago
This house was perfect for what we needed, a clean and quiet house with some fun game tables for entertainment! The area was lovely and we'd recommend it to anyone looking for a quiet spot close to shopping, restaurants, beaches, and beautiful CT shoreline. Vincent was very responsive and helpful. Thank you for having us!!
Guest favourite
Home in Guilford
5 out of 5 average rating, 24 reviews

Entire home - Cheerful 4 bedroom on the shoreline.

AshleyRating, 5 stars3 months 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!
Guest favourite
Home in Guilford
4.96 out of 5 average rating, 23 reviews

The Osprey Nest w/views of Long Island Sound

AlexRating, 5 stars1 month ago
This is a great place! I just finished my fourth visit (approaching 50 nights in this home) and I didn’t want to leave. Book this place if you want to wake up and drink coffee while watching sunrise in a second floor sun room or if you want a 1 mile walk to town (all sidewalks) and 200 meter walk to beach or if you want a place that’s stocked with kitchen utensils! I could go on and on. If it matters, it’s also not a corporate type Airbnb. Recommended!

Destinations to explore