House holiday rentals in Middlesex County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Middlesex County

House rentals with a pool

Top guest favourite
Home in Cutchogue
4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

EricRating, 5 stars7 months ago
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.
Guest favourite
Home in East Hampton
4.88 out of 5 average rating, 107 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars3 weeks ago
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.
Superhost
Home in Hampton Bays
4.94 out of 5 average rating, 127 reviews

Peaceful Retreat in Immaculate Architect’s House

ClareRating, 5 stars2 weeks ago
Michael was a great host, friendly, flexible and helpful. The house is beautiful and has all the amenities you would expect. We loved staying there and would definitely like to stay again.
Superhost
Home in East Hampton
4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars7 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Guest favourite
Home in Southampton
4.93 out of 5 average rating, 14 reviews

Southampton Escape, Heated Pool, hot tub, 3 bed,

LaurenRating, 5 stars10 months ago
The house was great! Our two infants loved the large deck and pool. So close to town and the beach. It was a perfect getaway!
Top guest favourite
Home in East Hampton
5 out of 5 average rating, 36 reviews

Stunning Central E. Hampton Home w/ gunite pool.

DonnaRating, 5 stars3 months ago
Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!
Top guest favourite
Home in East Marion
5 out of 5 average rating, 12 reviews

Long Island home w/ large pool

TautraRating, 5 stars2 months ago
My stay here was phenomenal! From the host’s response time, down to the amenities that were placed throughout the house. As soon as you walk in, it felt like home. The house is spacious and highly functional. The design of the house offers a perfect blend of modern mixed with nostalgic elements. The best stay by far. Would love to book again!

Weekly house rentals

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

Country getaway - huge yard, pool

KetwlyRating, 5 stars6 months ago
Our stay was wonderful. Lena is the perfect host. We are already talking about going back next fall!
Top guest favourite
Home in Old Lyme
4.94 out of 5 average rating, 269 reviews

Modern Luxurious CT Country Home

BetsyRating, 5 stars2 weeks ago
The natural setting surrounding the house is lovely and private. The house itself was spotlessly clean and very well stocked with linens, towels, and kitchen tools and supplies. The beds are very comfortable and it's quiet for sleeping. We spent most of our time in the all-glass kitchen, which despite so-so weather felt like we were outside when inside - really special room. Chris was very easy to reach and communicative for anything we needed. We enjoyed a wonderful extended family weekend and would stay again!
Superhost
Home in Westbrook
4.86 out of 5 average rating, 194 reviews

Family-Friendly Cottage by The Shore

TristanRating, 5 stars3 days ago
I had a nice, overnight stay at Marie's place. All was as described and the instructions for everything were spot on. Comfortable & convenient stay, would visit again!
Guest favourite
Home in Middletown
4.88 out of 5 average rating, 300 reviews

Historic Greek Revival Brick Home

JamieRating, 5 stars2 months ago
If you like antiques and a classic style home, Bill and Megan's place is for you. The woodwork and fireplaces were beautiful, and the space itself was simply charming. Check in directions were very easy to understand and we appreciated the off-street parking. The property was within easy walking distance to many shops and restaurants. We would definitely stay at this residence any time we visit Middletown.
Top guest favourite
Home in Madison
5 out of 5 average rating, 28 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

AlanRating, 5 stars1 month ago
Sascha was a terrific host and we had a wonderful stay at his home. The home was beautiful: plenty of space to spread out, relax, and everything was incredibly clean and tidy. It was also well-stocked with everything you could need. We appreciated Sascha's friendly demeanor, and he was a pleasure to communicate with. We hope to return here in the near future for another stay.
Guest favourite
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!
Guest favourite
Home in East Haddam
5 out of 5 average rating, 25 reviews

Elegant Countryside Estate

AnjaliRating, 5 stars4 months ago
Spent a wonderful Thanksgiving weekend at Travis' place with my husband and two young daughters. The house is beautifully appointed and so cozy. We played games by the fire, watched a movie in the cozy tv room, and made and enjoyed lovely meals in the kitchen. The house is even more magical than it looks in the photos, and we certainly hope to be back.
Superhost
Home in Westbrook
5 out of 5 average rating, 3 reviews

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

CarrieRating, 5 stars5 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, 49 reviews

The Davis House

WilliamRating, 5 stars3 months 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 Haddam
4.97 out of 5 average rating, 79 reviews

Winter at the Haddam House

ErynRating, 5 stars2 months ago
We had a wonderful weekend at John and Betsey's place! The house was clean and comfortable, with everything we needed, and the hosts were very kind and accommodating. It was super sweet to be there in the winter — totally fulfilling the wishlist my friend and I had for a quiet, mellow, extremely cozy weekend away — and we'd love to come back when can we be outside and fully enjoy the amazing location right on the river. It was very cold and snowy out and we couldn't have been more comfortable and toasty warm in the house. We didn't do very much in the area but there is a great market (with a wine/liquor store right next to it) just up the road, with really good meats and provisions for anyone wanting to cook, as we did. Thank you John and Betsey!
Guest favourite
Home in Clinton
4.96 out of 5 average rating, 25 reviews

Zaku’s Lake House

KathleenRating, 5 stars8 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!
Top guest favourite
Home in Guilford
5 out of 5 average rating, 18 reviews

Coast and Country Private Estate

AlisonRating, 5 stars6 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 stars3 months 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 stars8 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
4.82 out of 5 average rating, 50 reviews

Glass House-Close to the Beach,Outlets and Golf!

LuzRating, 5 stars3 weeks ago
Beautiful house and peaceful area to relax and enjoy extra time with your loved ones, and fun family activities right inside the house! Everything you need for a relaxing stress free getaway! The owners are very nice friendly family, they but a lot of attention and dedication to house to make it feel and look like your right at home. Love, Love, Love!
Top guest favourite
Home in Guilford
5 out of 5 average rating, 25 reviews

Entire home - Cheerful 4 bedroom on the shoreline.

AshleyRating, 5 stars5 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!

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