House vacation rentals in Fairfield County

Find and book unique houses on Airbnb

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Popular amenities for Fairfield County house rentals

House rentals with a pool

Guest favorite
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars7 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
Guest favorite
Home in Weston
4.93 out of 5 average rating, 15 reviews

Amazing Home w. Pool + Basketball Court on 3 Acres

EmmaRating, 5 stars3 months ago
The house was so gorgeous and comfortable! Warm kitchen, beautiful spaces to lounge, luxurious bathrooms, and spacious bedrooms. We felt very at home. And Dylan was very responsive. We had an overly exciting exit from the house due to snowy conditions and he raced over to help salt the driveway. Highly recommend a stay at his house — I can’t wait to come back in the summer and use the pool!
Guest favorite
Home in New Milford
4.95 out of 5 average rating, 21 reviews

Spacious and relaxing New Milford 5br home w pool!

ElizabethRating, 5 stars5 months ago
Jarret was extremely helpful and friendly. The house was exactly what we needed. I will definitely come back and stay here next time I’m in town.
Top guest favorite
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!
Superhost
Home in Carmel Hamlet
4.75 out of 5 average rating, 4 reviews

Stone Cottage

LauraRating, 5 stars4 months ago
The stone cottage was the perfect getaway for our New Years trip! The space is cozy and well appointed, and the host was thoughtful and accommodating when we ended up arriving in town earlier than anticipated. We would love to come back and stay in the summer to sit by the pool in such private and peaceful surroundings.
Guest favorite
Home in Stamford
4.96 out of 5 average rating, 247 reviews

Midcentury Modern ZenHouse Sculptor Studio

GonzaloRating, 5 stars1 week ago
I stayed here for a weekend and I wished I would have stayed longer. Perfect spot for a getaway and relaxation. Olga was a really caring and warm host, super attentive at all time, always saved some food for us when she cooked. The house was clean, organized, with natural lighting everywhere surrounded by a beautiful garden and a river with ducks and a swan. I would recommend this place to anyone who’s looking to relax, have a weekend to themselves and enjoy nature.
Guest favorite
Home in North Salem
4.94 out of 5 average rating, 32 reviews

North Salem Home with Pool & Great Yard

MauricioRating, 5 stars4 days ago
Exactly what my family needed for a quiet getaway from the city. The huge yard and quiet surroundings were a blessing. Made friends with the woodpecker while enjoying a cup of coffee on the patio :) The house is well equipped and kept immaculate. the weather helped in allowing us to both enjoy the warmth of the fireplace, while also enjoying the hammocks. We loved our stay so much that we extended our stay by three days. Susan is a great host and is very thoughtful and friendly. I highly recommend this home to anyone ! Looking forward to coming back.,
Top guest favorite
Home in Roxbury
5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars2 months ago
My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.

Weekly house rentals

Superhost
Home in Fairfield
4.86 out of 5 average rating, 81 reviews

Bright 3-bedroom house with ample parking & patio!

AiméeRating, 5 stars2 months ago
My friends and I had a wonderful time at Alyson & Costa's Fairfield house! It's an absolutely adorable space in a great area. The hosts are responsive, helpful, and kind. I would recommend this Airbnb to anyone looking to stay in this area!
Top guest favorite
Home in Pawling
5 out of 5 average rating, 223 reviews

Hobbit House of Pawling

MatthewRating, 5 stars6 days ago
This place exceeded our expectations! An incredible place that was clearly a labor of love to build, decorate and maintain. I don’t imagine anyone who stays here will be disappointed - or soon forget their visit to this lovely property. Not only is it carefully and cleverly curated as a habitable homage to The Hobbit and the LOTR, it is also a genuinely comfortable and charming place to stay. The kitchen is well-equipped and the bathrooms are roomy and modern. Lots of outdoor spaces to enjoy, including the hot tub, nestled at the foot of a dramatic, rocky rise. Thanks to Jodi and Jim!
Superhost
Home in Pound Ridge
4.86 out of 5 average rating, 49 reviews

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

PaulRating, 5 stars2 weeks ago
We had a great time at this lovely, antique home, complete with gardens and great big back yard! Bob, our Corgi, definitely approved! Easy access to Stamford and Bedford! Thanks for your thoughtful arrangements!
Superhost
Home in Stamford
4.94 out of 5 average rating, 115 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

DebraRating, 5 stars2 weeks ago
Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!
Guest favorite
Home in Brookfield
4.82 out of 5 average rating, 22 reviews

Lake Candlewood Retreat

FabioRating, 5 stars5 months ago
Nice place .. host is very responsive and helpful and place is nice .. beautiful lake views .. spent 30 days while renovating my house Nd was a smooth stay..
Superhost
Home in Greenwich
4.8 out of 5 average rating, 100 reviews

Greenwich abode Close to Just about Everything

ChrisRating, 5 stars3 months ago
Please stay here and support Nicole.. what a wonderful host Comfortable, clean and safe home Snow storm hit overnight and we woke up to the sidewalk and steps already shoveled and salted … she even offered to dig out our car if the snow was piled up high enough Nicole was very proactive with great communication but we did not feel bothered Plenty of street parking right by the house We really enjoyed watching the ducks and other water fowl in the stream behind the house A little bit of nature to relax after a day in the city Thanks Nicole, we will be back to stay in your home again
Top guest favorite
Home in Stamford
4.98 out of 5 average rating, 232 reviews

Bright Stylish Chic 4BR 4BA Home

ShefaliRating, 5 stars1 month ago
We had a wonderful time at Deirdre’s place which was a last minute booking. She was very responsive and we felt so much at home, with everything we needed to keep our family of 5 safe and occupied. We especially loved the playroom and books for all ages. The backyard tire swing and bird watching was a hit with my bigger kids too. There was lots of space to spread out if we had come with more family as well. Great stay- thank you again, Deirdre!
Guest favorite
Home in Fairfield
4.9 out of 5 average rating, 106 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

Corri AnnRating, 5 stars2 months ago
John and Crystal were super hosts. They communicated thoroughly and responded quickly, were flexible, and above all made us feel right at home. The location is close to everything and very quiet. The accommodations were extremely comfortable, and even though there wasn't a full kitchen, the items they provided were more than enough for our stay. The off street parking was optimal and when it did snow during our visit someone was there first thing to shovel. We appreciated the flexibility of the hosts and extended our stay. John and Crystal made our travels super easy and stress free that I know we will request to stay again! Thank you!!

Private house rentals

Guest favorite
Home in New Fairfield
4.95 out of 5 average rating, 79 reviews

The Lakeside Nook

MarisaRating, 5 stars3 weeks ago
A perfect place for our family trip. Nestled in a peaceful beautiful area, close to the pond/lake. The home was so cozy and Monika was so responsive to our messages. Definitely would stay there again
Top guest favorite
Home in Wilton
5 out of 5 average rating, 15 reviews

Nature Retreat on 2.5 Acres

Mary AnnRating, 5 stars1 week ago
My family and I had a lovely Easter stay at Klaira's house. The home is very nicely laid out and well equipped. The beds are very comfortable and everything was spotless. There is a nice outdoor deck and gazebo area but the weather was a bit chilly so we did not get a chance to enjoy. We are familiar with this part of Connecticut so we had lots to do. The beautiful Weir Farm National Historic Park is nearby as are hiking trails and good restaurants a short drive away in Ridgefield and in Wilton. I recommend Klaria's comfortable house rather than a hotel for anyone looking for a family gathering spot for your New England stay.
Superhost
Home in Fairfield
4.81 out of 5 average rating, 123 reviews

Southport Shoreline Charm: Elegant Coastal Escape

OctavioRating, 5 stars1 month ago
Our stay was absolutely wonderful from start to finish! The accommodations were clean, comfortable, and well-maintained, with thoughtful touches that made us feel right at home.
Top guest favorite
Home in Middlebury
5 out of 5 average rating, 11 reviews

New England Charm!

DavidRating, 5 stars6 days ago
I've stayed her many times for business trips. Always convenient, comfortable and quiet. Meets my needs ideally.
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 favorite
Home in New Milford
4.97 out of 5 average rating, 106 reviews

Idyllic retreat on the water <1.5 hrs to NYC.

BenjaminRating, 5 stars1 week ago
Jonathan’s home was a great find - such a beautiful spot on the river. Everything about the home and property was as described and Jonathan was a friendly and communicative host. I would definitely book again!
Superhost
Home in Washington
4.89 out of 5 average rating, 18 reviews

A newly renovated country house in Washington

GeorgiaRating, 5 stars17 months ago
Such a lovely home in a fabulous location. We had an amazing time and hope to stay again.
Guest favorite
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.

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