House vacation rentals in Fairfield

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Popular amenities for Fairfield house rentals

House rentals with a pool

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

The Perfect North Fork Escape

EricRating, 5 stars8 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 stars3 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.
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.
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
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 Shirley
5 out of 5 average rating, 16 reviews

Hope Haven

HilarioRating, 5 stars8 months ago
I was in Dion’s place with my family we really enjoyed the time we spent there,everything was perfect the pool was something that my kids enjoyed a lot, and hopefully we will come back again, for sure I totally recommend his house if you want to go and have a couple days of fun and relax thank you again Dion.
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, 169 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

ChristiRating, 5 stars6 days ago
We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.

Weekly house rentals

Guest favourite
Home in North Fork
4.98 out of 5 average rating, 43 reviews

Private pool/walk to beach; farms/vineyards abound

SuzanneRating, 5 stars7 months ago
Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.
Superhost
Home in Hampton Bays
4.79 out of 5 average rating, 106 reviews

Private completely fenced in property. Near beach.

CandiceRating, 5 stars2 weeks ago
AJ is an AWESOME host!!!!! We loved staying at this property. It's so safe and way bigger than the photos. The bathrooms are fantastic. (No bathtubs, though, if you need one.) I cannot emphasize what a great stay we had. Thank you so much!!!!!
Superhost
Home in Westbrook
4.86 out of 5 average rating, 194 reviews

Family-Friendly Cottage by The Shore

TristanRating, 5 stars1 week 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!
Top guest favourite
Home in Philipstown
4.93 out of 5 average rating, 129 reviews

Cozy 3 bedroom house on quiet private road

ScottRating, 5 stars1 month ago
Having a current child / Cadet at West Point and also another child / graduate of West Point , we always make it a point to stay at different Airbnbs in small towns around the USMA on both sides of the Hudson River . Melanie ‘s place was wonderful. Plenty of rooms/ beds for our Parent Weekend visit. Peaceful and safe location , yet a short 20 minute drive to the Academy . We felt right at home and look forward to staying at Melanie’s place again . The house was very clean and we had no issues at all !! Thank you
Superhost
Home in White Plains
4.88 out of 5 average rating, 8 reviews

Indigo Inn III -A Retro Modern Cove White Plains

ShannonRating, 5 stars7 months ago
Great space. Wonderful communication with host regarding any questions we had. Host was quick to respond. Very happy with the stay, would rent again.
Guest favourite
Home in Garrison
4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars3 weeks ago
Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!
Guest favourite
Home in Syosset
4.9 out of 5 average rating, 51 reviews

Elegant, resort style, clean, north shore home

FredRating, 5 stars9 months ago
The inside and outside areas were meticulously maintained. The weather was great, so we were able to really enjoy the pool and deck. Michelle was extremely responsive and did a great job with instructions, recommendations, and communications. One member of our party needed to work a few days, and the office space in the basement was perfect.
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

Guest favourite
Home in Chester
4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

TimRating, 5 stars6 months ago
We'd been looking forward to coming back to The Recycle House since we first stayed there in 2022. Safe to say it was just as we remembered it...great house, great location, wonderful community. Looking forwarded to returning.
Guest favourite
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars3 weeks ago
It was wonderful stay and I’d go back anytime
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Superhost
Home in Ridgefield
4.81 out of 5 average rating, 21 reviews

Log House, sits on 3acres. A retired mini farm.

TaylorRating, 5 stars3 weeks ago
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)
Top guest favourite
Home in Philipstown
5 out of 5 average rating, 26 reviews

Charming Retreat 3B/3B Garrison, 2 Fireplaces

BibiRating, 5 stars5 months ago
There were 5 of us, with another 6 staying in another nearby air bnb. We had Thanksgiving in our house and found everything we needed to cook. Seating was a bit challenging, but we made it work and it was very comfortable. The location is in the woods with lots of boulders and rocks, which we all loved. We found the place easily using GPS. Everyone’s bed was comfy. Close enough to what we wanted, just far enough away to make it an adventure. Because it was so cold and grey, we didn’t hike, but saw plenty of opportunities (maybe next time?!)
Top guest favourite
Home in Woodmont
4.92 out of 5 average rating, 256 reviews

Bright and Breezy Cottage by the Sea

RachelRating, 5 stars5 days ago
My family and I have stayed at a ton of different airbnbs, vrbos and vacation rentals both stateside and abroad and I have to say Anne’s property is among one of the best we’ve stayed in. We were traveling with twin toddlers and the space was perfect. Anne is very friendly, the place is larger than we expected, very clean and you can tell Anne cares to the make the best experience possible. All the little touches were so wonderful - she has beach chairs, reusable beach bags, sunscreen, books, kids toys, coloring accessories, balls and toys, an outdoor game, hammock, lanterns, lights, fire pit and wood, you name it - it’s there. It was one of the most convenient stays we’ve had. We’d love to return and I couldn’t recommend it enough!!
Guest favourite
Home in Norwalk
4.89 out of 5 average rating, 37 reviews

Entire House on Scenic Estate with Private Pond

KristyRating, 5 stars1 month ago
We had a lovely stay. JP was extremely responsive and accommodating. The house was exactly as stated in the listing. We would stay there again if in the area.
Guest favourite
Home in Stratford
4.94 out of 5 average rating, 174 reviews

Cozy Colonial - Private Hot Tub & Entire House

MonicaRating, 5 stars1 month ago
We loved our stay! Dylan was extremely responsive and the home was exactly as explained. The rooms were spacious and the beds were so comfy! No complaints! We will definitely stay again when we visit family.

Quick stats about house rentals in Fairfield

  • Total rentals

    210 properties

  • Total number of reviews

    3.4K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

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