House holiday rentals in Fairfield County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Fairfield County

House rentals with a pool

Superhost
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Guest favourite
Home in Holmes
4.91 out of 5 average rating, 11 reviews

Enchanted Escape | POOL, LAKE, Concierge Services

AnxhelaRating, 5 stars3 weeks ago
We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars1 month ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Superhost
Home in Milford
4.84 out of 5 average rating, 91 reviews

Spacious 4 bedroom, oasis with ocean views galore

ChrissyRating, 5 stars1 week ago
We had a wonderful girls weekend at Allana’s house by the sea! When we had a small incident with the keypad, Allana was quick to answer my call and resolve the issue no problem. Everything was clean and beautiful! We especially enjoyed the screened in porch in the back to enjoy our meals. The view from the master bedroom and deck is incredible! We highly recommend and will be back!
Guest favourite
Home in Manorville
4.98 out of 5 average rating, 255 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

SolomonRating, 5 stars1 month ago
This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!
Guest favourite
Home in Greenwich
4.96 out of 5 average rating, 45 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

Rich Rating, 5 stars1 week ago
A truly Great stay in Greenwich with David, we really enjoyed our stay in the house, such an awesome place and quiet location (next to a beautiful river!) too, which we loved. The pool was a massive bonus for sure! Comms with David were great, he was very quick to respond at all times on any queries we had, much appreciated indeed. Many thanks again, Rich
Guest favourite
Home in Port Jefferson
4.92 out of 5 average rating, 125 reviews

Port Jefferson Convenient, Cozy and Chic!

DaleRating, 5 stars2 weeks ago
We we’re going to Port Jefferson for a family wedding. Our Airbnb was perfectly situated. There is a pool area that we never used because we just didn’t have time. But it looked very inviting. The town of Port Jefferson had plenty of nice restaurants and shops. This house was perfect for our situation. We had six adults, all family members.
Guest favourite
Home in Litchfield
4.93 out of 5 average rating, 190 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

PaulRating, 5 stars5 days ago
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

Weekly house rentals

Guest favourite
Home in Easton
5 out of 5 average rating, 29 reviews

Historic Designer City Getaway

FayRating, 5 stars3 weeks ago
We thoroughly enjoyed our stay at this historic house. It is full of character: we especially loved the massive fireplace where meals were presumably prepared back when it was an inn in the 1700s. It is also ridiculously spacious and very well furnished and equipped for a group of 10: the dining table easily seats 10, there is ample comfortable seating in the living room (not to mention at least 3 other sitting rooms one could gather in), and 8 of us were simultaneously cooking in the kitchen without anyone bumping elbows. Cooking here is a dream: there is a 6-burner+grill stove, 2 ovens, and all the equipment you could want (including a KitchenAid stand mixer and Vitamix blender). Moreover, Carly was an excellent host: she was always quick to respond, her messages were clear, and she generously allowed us to stay an extra hour to make our timing work out well. We highly recommend this house and would love to return.
Superhost
Home in Newtown
4.86 out of 5 average rating, 7 reviews

Serenity by Lakefront Cottage!

LuisRating, 5 stars4 weeks ago
Definitely recommend will be there another time thanks
Guest favourite
Home in New Fairfield
4.95 out of 5 average rating, 82 reviews

The Lakeside Nook

SarahRating, 5 stars4 weeks ago
Our stay was peaceful, and relaxing, full of beauty and the comfort of home-away-from-home. We enjoyed hiking and exploring the beautiful natural surroundings, cute shops and restaurants in nearby towns, and just resting in this beautiful home. Monika was a great communicator, highly responsive and created a fully equipped, beautifully curated space for our family's stay. I highly recommend and will definitely rebook the next time we are back in the area!
Top guest favourite
Home in Newtown
5 out of 5 average rating, 16 reviews

A nestled retreat on 15 acres

SusanRating, 5 stars2 weeks ago
We loved this house, it's beautiful inside and out. We watched deer in the early morning and had a dozen or more flowering trees dotting our view. The house is immaculate, and the kitchen is a dream for prepping and cooking. We were able to visit Yale, ocean beaches, wonderful restaurants, and ran into two farmers markets full with welcoming artists.. we had a rainy evening and enjoyed listening to the rain while we read. It's a great location if you want to do a Gilmore Girls weekend. If you know, you know. Thank you Kathleen for sharing your home.
Superhost
Home in Fairfield
4.81 out of 5 average rating, 127 reviews

Southport Shoreline Charm: Elegant Coastal Escape

TracieRating, 5 stars1 month ago
Just as described. Clean and comfortable. Location was great for Fairfield University graduation. The patio was a little lack luster but we were not planning to use it anyway. (maybe it was the time of year we were there). Glad I was aware of the traffic noise ahead of time, however it really turned into background noise and not an issue. If back in the area, we would certainly look to stay with Drew again. We would also recommend to others.
Top guest favourite
Home in Milford
4.98 out of 5 average rating, 54 reviews

Luxe Beach House | 3 Bd-King | Chef Kitchen | 4 TV

LeahRating, 5 starstoday
What a great place to stay! Beautiful view from the house, which was also gorgeous. Well decorated and clean! A short drive into town where there are a ton of great restaurants. Loved how easy it was to get to the beach from here as well.
Top guest favourite
Home in Newtown
4.99 out of 5 average rating, 96 reviews

Comfortable home away from home

AaronRating, 5 stars2 weeks ago
Terry and Jack’s place was perfect for us staying in Newtown visiting friends but we could also drive to Manhattan for day trips. House had everything you’d need and they even helped us get a crib delivered early/picked up later after we left. Super nice and responsive hosts! Will definitely stay again!
Guest favourite
Home in Redding
4.91 out of 5 average rating, 87 reviews

Nature Retreat Airbnb

JenniferRating, 5 stars1 month ago
This ouse is a beautiful home in a beautiful setting. Peaceful and private. Well maintained. Spacious and very clean. Comfortable beds and very cozy bedrooms. We loved our stay in Redding. Thank you for being such wonderful hosts.

Private house rentals

Superhost
Home in Fairfield
4.85 out of 5 average rating, 87 reviews

Bright 3-bedroom house with ample parking & patio!

AlexaRating, 5 stars3 weeks ago
We have stayed at a number of Airbnbs and this is one we would definitely consider returning to in the future. The price was right and Alyson was super responsive to the couple of questions we had. Everything was really clean, the space was very comfortable, and we really liked the kitchen and the back family room area. There wasn't anything lacking in the kitchen and the fact that there was a washer and dryer really put it at the top of our list for return visits.
Guest favourite
Home in Branford
4.97 out of 5 average rating, 36 reviews

Adorable Beach House on LI Sound

LisaRating, 5 stars2 days ago
There’s so much to love about this charming open plan beach cottage! We especially enjoyed the water views, hearing the birds, and eating on the breezy porch. It was sparkling clean and stocked with everything you’d need, from comfortable beds and towels to many thoughtful essentials like hand and dish soaps, tea and coffee pods, paper towels/toilet paper, and shampoo/conditioner. Eileen is a gracious and responsive host — she was particularly understanding when we had to reschedule our visit. Thank you for a wonderful stay, Eileen, and we hope to return!
Top guest favourite
Home in New Milford
4.97 out of 5 average rating, 31 reviews

OWL's PERCH Candlewood Lakefront Rustic Cottage!

JackieRating, 5 stars1 week ago
If you're looking for a cute little cottage in the woods near the lake to recharge and relax - this is it! KC provided an extensive list of instructions and to know's, which made check in/check out and all the in-between fool proof. KC was super friendly and responsive as well!
Guest favourite
Home in Pleasant Valley
5 out of 5 average rating, 27 reviews

The Wildflower House

MatthewRating, 5 stars1 month ago
Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!
Guest favourite
Home in Fairfield
4.96 out of 5 average rating, 24 reviews

Remodeled Cozy Country Cape

EllieRating, 5 stars2 weeks ago
Karen's home was a great place to stay for our 10 year college reunion. Plenty of space for 2 couples and great location.
Guest favourite
Home in Fairfield
4.92 out of 5 average rating, 24 reviews

Seaside Home - Walk to Beach & Marina

MichaelRating, 5 starstoday
We loved staying in Angela’s home. Close to restaurants and walkable to the beach and marina. We spent a lot of time outside in the back yard, it was so peaceful back there. Instructions, tips and things to do are all laid out and Angela answered our questions promptly when we had any. Great stay!
Top guest favourite
Home in Trumbull
5 out of 5 average rating, 36 reviews

Cozy, updated single family in Fairfield County

ZulmaRating, 5 stars2 months ago
Beautiful home would definitely rent again and recommend to family and friends. Thanks Jennifer.
Top guest favourite
Home in Cold Spring
5 out of 5 average rating, 43 reviews

Mountain Top Retreat

MaryRating, 5 stars4 days ago
Very comfy bed… great shower- lots of hot water and good water pressure. The bottled water, oatmeal and snack bars were appreciated. The home was clean and spacious. Back deck was a perfect spot to unwind. Andre and his wife were very helpful.

Destinations to explore