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

Superhost
Home in Hampton Bays
4.79 out of 5 average rating, 107 reviews

Private completely fenced in property. Near beach.

VictoriaRating, 5 stars2 days ago
Four adult ladies enjoyed this beautiful home in the perfect location for our best friend’s weekend trip! House was clean, had everything we needed, all 4 beds are very comfortable and rooms spacious! AJ was very responsive and attentive to our requests . We visited several vineyards in the area during our stay and loved all host recommendations (Borghese Vineyard, Rose Hill & Sparkling Pointe were our top favs!), Centro 336 is the perfect spot for a delicious dinner, Hampton Maid literally best brunch and Hampton Coffee Company is our top choice for a caffeine fix! Tony’s Asian Fusion via Uber Eats hit the spot on our 1st night in after long drive. It was also beneficial to have a few supermarkets, Dollar Tree and other stores within a mile of the property , to grab a forgotten item {or 2 as we did!}! We also used North Fork Designator Driver services for vineyard trips, highly recommend! Love this location and grateful for the amenities and privacy it offered us!
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 stars1 month 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.
Top Guest favourite
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars3 weeks ago
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.
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 stars4 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!
Guest favourite
Home in Hampton Bays
4.89 out of 5 average rating, 100 reviews

Hamptons Escape minutes from Beaches and Nightlife

EricaRating, 5 stars1 week ago
Our family spent a great weekend here. There was plenty of rooms for everyone to have their own, and everything was clean, cozy, and comfortable. The home was exactly as shown in the pictures and everything we could have needed was there. The hot tub was lovely both nights, and the pool area looks pretty though was not yet opened for the season. This is a perfect spot to bring your family, to relax, and enjoy all that the Hamptons, and Hampton Bays has to offer. We hope to return soon!
Top Guest favourite
Home in East Marion
5 out of 5 average rating, 12 reviews

Long Island home w/ large pool

TautraRating, 5 stars3 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!
Superhost
Home in East Hampton
4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

LarryRating, 5 stars47 months ago
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

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 stars1 month 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
4.85 out of 5 average rating, 195 reviews

Family-Friendly Cottage by The Shore

TristanRating, 5 stars2 weeks 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, 303 reviews

Historic Greek Revival Brick Home

EmmaRating, 5 stars3 weeks ago
Friendly and responsive! Just what we needed.
Superhost
Home in East Hampton
4.75 out of 5 average rating, 28 reviews

Charming River Home

CourtneyRating, 5 stars4 months ago
This was a great location for our family of 7. There were enough beds, good amenities, and it was a great location to get down to the Connecticut River. It was centrally located and we were able to explore many cities in CT due to the location. The hosts were extremely responsive and the home was well-maintained.
Top Guest favourite
Home in Madison
5 out of 5 average rating, 28 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

AlanRating, 5 stars2 months 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, 41 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars4 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 Madison
4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars6 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.

Private house rentals

Superhost
Home in Guilford
4.88 out of 5 average rating, 49 reviews

The Davis House

WilliamRating, 5 stars4 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 East Haddam
5 out of 5 average rating, 25 reviews

Elegant Countryside Estate

AnjaliRating, 5 stars5 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 Essex
4.95 out of 5 average rating, 19 reviews

Hyde House-A classic New England cape.

SofiaRating, 5 stars4 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
4.83 out of 5 average rating, 52 reviews

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

JessicaRating, 5 stars2 weeks ago
We had a wonderful stay at this beautiful family home in Connecticut! The house was spotless, cozy, and had everything we needed for a comfortable stay. The kitchen was fully stocked, the beds were super comfortable, and there was plenty of space for our family to relax and spend time together. The neighborhood was peaceful and safe, with great access to local shops, restaurants, and some lovely nature spots. The host was incredibly welcoming and responsive, making the whole experience smooth from start to finish. Highly recommend this home for anyone looking for a relaxing family getaway in a charming part of Connecticut!
Guest favourite
Home in Guilford
4.96 out of 5 average rating, 24 reviews

The Osprey Nest w/views of Long Island Sound

AlexRating, 5 stars4 months 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!
Guest favourite
Home in Clinton
4.95 out of 5 average rating, 20 reviews

Welcome To Pleasant Valley House

SandraRating, 5 stars1 week ago
This house is located in a beautiful neighborhood in Clinton. The backyard is very large and provides a serene landscape. There is ample space in the house, and the bedrooms are large with a lot of closet space. Beds and pillows were high quality and very comfortable. The location is great because you are so close to I95 and local back roads. You can get to neighboring towns very quickly i.e. Madison, Westbrook, Old Saybrook, Guilford. We know the area well because we used to live there, and would definitely stay there again on our next trip. Zoey and Paul were great hosts!

Destinations to explore