Family-friendly holiday rentals in Middlesex County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Middlesex County family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Condo in Norwich
4.84 out of 5 average rating, 150 reviews

Villa Flora @ Norwich Inn & Spa

DebraRating, 5 stars6 months ago
There is nothing more frustrating than not being able to have a decent shower while you are on vacation. That was absolutely not the case here. The hot water and water pressure in both bathrooms was exceptional. This is a great place in a great area. We will definitely try to get back here.
Guest favourite
Home in Cutchogue
4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

KimRating, 5 stars4 months ago
This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!
Top Guest favourite
Home in Wading River
4.96 out of 5 average rating, 499 reviews

Your Zen Retreat

DanielleRating, 5 stars1 month ago
Myself and a few friends stayed here to celebrate a 40th birthday and we all loved it! The space is so unique yet still cozy and very relaxing. We were able to cook easily in the fully stocked kitchen all of the bedrooms were comfortable. Spent a majority of our time just hanging in the living room, but did get around to utilizing the hot tub. Would highly recommend this place for a nice relaxing weekend away.
Top Guest favourite
Cottage in Southampton
4.96 out of 5 average rating, 184 reviews

Secluded Southampton Cottage w/Pool & Spa

TaylorRating, 5 stars2 months ago
sweet, comfortable cottage close to everything, but feels tucked away and private. lovely for off season with the fireplace and hot tub.
Guest favourite
Cabin in Riverhead
4.86 out of 5 average rating, 102 reviews

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

AllisonRating, 5 stars3 months ago
We had a fabulous time! Can't wait to come back. Was equally perfect for two toddlers as it was for four adults! Beautiful property, amazing hot tub, comfortable beds, great kitchen... everything was lovely.
Guest favourite
Home in East Hampton
4.94 out of 5 average rating, 161 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

RichardRating, 5 stars4 weeks ago
Cozy and pretty home, all ready for a chill weekend. Cindy is super nice and easy to work with. Very generous too. The 2 pups loved the fenced in yards. Kitchen/dining room space is big and bright and awesome to hang out or read in the corner nook. I am sure the backyard and pool would be great in summer. Beds were comfortable. Thank you Cindy!
Guest favourite
Home in Shelter Island
4.88 out of 5 average rating, 24 reviews

Newly Renovated w/ Pool, Hot tub & Fireplace

AliciaRating, 5 stars6 months ago
We had a wonderful stay at Jennifer’s place. It was.l beautiful, immaculate, and incredibly well equipped—especially for kids with the plethora of games and toys. Jennifer was responsive and a great host. The house is on a serene, dead-end street, and outdoor area is perfect for kids.
Guest favourite
Villa in Norwich
4.89 out of 5 average rating, 398 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

BiancaRating, 5 stars2 weeks ago
Beautiful spot - great for a girl’s getaway with everything we could possibly need! Flexible host & great communication. We can’t wait to come back!

Family- and pet-friendly home rentals

Home in East Hampton
4.77 out of 5 average rating, 52 reviews

MAGNIFICENT PRIVATE RIVERFRONT HOME, 10% off

KathleenRating, 5 stars22 months ago
This AirBnB was great for our family that was there for a family wedding. The views of the river were beautiful and changed with every level of the decks! Dean was always responsive to any questions we had. Thank you for our lovely stay!!
Superhost
Apartment in East Haddam
4.79 out of 5 average rating, 280 reviews

The Federal Suite at the Wisteria Rest

AlcindaRating, 5 stars2 months ago
Loved the tasteful decor, and the way this historic home has been modernized yet still holding its victorian charm. Many nice touches, and everything was nicely arranged. The bedroom is spacious and lovely. My daughter and I thoroughly enjoyed our time together staying at Lizzy's place.
Top Guest favourite
Home in Guilford
4.97 out of 5 average rating, 66 reviews

Shoreline Cottage by Beach; Birder's Paradise

EricaRating, 5 stars6 months ago
Amy’s place was a great location for our weekend getaway for a fan festival in town! The house had everything we needed, no issues at all, instructions were provided for anything and everything. Perfect host, great house and location! Thank you!
Guest favourite
Apartment in Guilford
5 out of 5 average rating, 6 reviews

Lakefront Country Oasis

SergioRating, 5 stars9 months ago
Margie’s place is an amazing hidden gem. The inside is very clean and comfortable. The outside is an experience of its own. The lake will drop your blood pressure immediately. Gorgeous surroundings. The dogs are friendly and lovable. We will be back! 👍🏼
Guest favourite
Loft in Essex
4.94 out of 5 average rating, 437 reviews

Unique apartment in former art gallery.

ChristinaRating, 5 stars1 month ago
I really enjoyed my stay here. The place was eclectic and comfortable. I loved how open and spacious the home was and appreciated the peacefulness of the area. I would definitely stay here again on future visits.
Home in Old Saybrook
4.95 out of 5 average rating, 41 reviews

Escape to our Waterfront House In Old Saybrook CT

AlanRating, 5 stars19 months ago
Nice place, great location house was as described in listing
Home in Lyme
4.9 out of 5 average rating, 91 reviews

Luxurious country guest house

ElaineRating, 5 stars9 months ago
The house was very peaceful and quiet. Caryn owns three alpacas and a sheep and they were adorable and fun to watch. The house was very rustic and comfortable and very well equipped. Caryn was an amazing host. She was at the house to greet us when we arrived and was very accommodating with any questions that we had. She couldn't do enough to make our stay perfect.

Family-friendly home rentals with a pool

Guest favourite
Home in East Hampton
4.93 out of 5 average rating, 109 reviews

Private & Pristine with Pool and Kid’s Playard

StephenRating, 5 stars4 months ago
Marta’s place was the perfect getaway for my family. The bedrooms were large with comfortable beds. The kitchen was huge with high end appliances, and the yard was a dream for our young dog. Lovely surroundings in the woods but close to town for shopping and restaurants. Truly an unforgettable experience!
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.
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!
Guest favourite
Home in Sag Harbor
4.85 out of 5 average rating, 262 reviews

Exclusive Sag Harbor Compound

WyattRating, 5 stars4 months ago
We loved our stay here. The house was sparkling clean and the yard was big and beautiful. Can only imagine the vibes here during the summertime when the pool is open!
Top Guest favourite
Home in Hampton Bays
4.98 out of 5 average rating, 126 reviews

Beach House Feel - newly renovated backyard Oasis

LaurenRating, 5 stars7 months ago
We absolutely loved staying at Christine’s beautiful home! The place was immaculate, and we particularly enjoyed the pool and fire pit. The location was perfect—situated in a quiet neighborhood, close to great restaurants, and within walking distance of the water. Christine was an amazing host, letting us check in early and check out late. She also texted to make sure we had everything we needed and were enjoying our stay. She even stopped by to share some great recommendations and ensure we knew how to use the house and pool code. We had a fantastic experience and would highly recommend this Airbnb to anyone looking for a relaxing and enjoyable stay!
Guest favourite
Home in Southampton
4.96 out of 5 average rating, 166 reviews

POOL in APRIL! Waterview, Free For Dogs! Kayaks

MeganRating, 5 stars1 week ago
The house is beautiful! Great location. Amy and Roger were extremely helpful and responsive. Lots to do! We had an amazing visit!
Guest favourite
Home in East Hampton
4.93 out of 5 average rating, 147 reviews

Large heated pool, games room, near private beach

José CarlosRating, 5 stars3 weeks ago
We had a great time. The house was really big and perfect for a big group. The common areas allowed us to spend time together and there was so much to do in the house and in its surroundings. We definitely recommend it.

Destinations to explore