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House holiday rentals in Fairfield

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Fairfield

House rentals with a pool

Guest favourite
Home in Stormville
4.94 out of 5 average rating, 180 reviews

Private Hudson Valley Country Retreat

KeerthiRating, 5 stars2 weeks ago
Our second time here. Great spot for our family of 4, and Sandy is very responsive
Superhost
Home in Hampton Bays
4.95 out of 5 average rating, 129 reviews

Peaceful Retreat in Immaculate Architect’s House

TheanoRating, 5 stars1 month ago
We had an amazing stay at Michael’s Airbnb this past weekend! The space was exactly as described—clean, cozy, and well-equipped with everything we needed. Michael was a fantastic host: super responsive, thoughtful, and made us feel completely at home. The location was perfect for a relaxing getaway, and the setting was even more beautiful in person. Would absolutely stay here again—thank you for a wonderful experience, Michael!
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 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 Commack
4.99 out of 5 average rating, 139 reviews

GOOD VIBEZ HOUSE! MiniGolf-Pool-HotTub-GameRm!

AliceRating, 5 stars2 weeks ago
We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!
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 North Fork
4.97 out of 5 average rating, 151 reviews

Secluded Farmhouse - Studio Apartment Style Unit

LeslieRating, 5 stars2 weeks ago
Jessica's place was serene and exactly what we were looking for during our long weekend in the North Fork. Great communication!
Guest favourite
Home in Port Jefferson
4.92 out of 5 average rating, 124 reviews

Port Jefferson Convenient, Cozy and Chic!

DaleRating, 5 stars4 days 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.
Top guest favourite
Home in Pound Ridge
5 out of 5 average rating, 163 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MollieRating, 5 stars2 weeks ago
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.

Weekly house rentals

Top guest favourite
Home in Trumbull
4.97 out of 5 average rating, 38 reviews

The Elijah Sterling House

CarolynRating, 5 stars4 days ago
Excellent stay overall! Would highly recommend this AirBnB. I always appreciate special touches like a bottle of wine, guest book, and binder detailing the history of the home and local restaurant recommendations. We loved Plasko’s for coffee and ice cream. Great place to stay when visiting Fairfield U!
Guest favourite
Home in Easton
5 out of 5 average rating, 28 reviews

Historic Designer City Getaway

FayRating, 5 stars2 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.
Top guest favourite
Home in Black Rock
4.98 out of 5 average rating, 54 reviews

Stay at Black Rock Harbor

TheresaRating, 5 stars3 days ago
⸻ Great Stay in a Lovely Black Rock Neighborhood We really enjoyed our stay at 65 Calderwood Court. The house was clean, comfortable, and well-equipped with everything we needed. The kitchen had plenty of supplies, and the beds were cozy after a full day of exploring. The location was excellent, just a short walk to Seabright Beach and close to local shops and restaurants. Staying during Black Rock Day was a nice bonus; we could easily join in the festivities and then retreat to a quiet, comfortable home. Allie was responsive and made the check-in process smooth. Overall, a very pleasant experience, and we’d happily stay here again when visiting the area.
Top guest favourite
Home in Woodmont
5 out of 5 average rating, 96 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars1 week ago
We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!
Guest favourite
Home in Bridgeport
4.9 out of 5 average rating, 50 reviews

Lavish retreat near downtown

LauraRating, 5 stars1 week ago
we love the place, Natalie was always communicative and helpful. well equipped the apartment definitely 100% recommended to anyone.
Superhost
Home in Fairfield
5 out of 5 average rating, 3 reviews

Coastal Lifestyle

RachelRating, 5 stars11 months ago
Super great place with lovely sunset and super walkable everywhere. Jin was very responsive, thoughtful and helpful with anything we needed. She even provided baby shower wash!
Guest favourite
Home in Redding
4.88 out of 5 average rating, 16 reviews

Meeker Hill House - Country Escape w/ Heated Pool

RoryRating, 5 stars8 months ago
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend
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.

Private house rentals

Guest favourite
Home in Branford
4.97 out of 5 average rating, 33 reviews

Adorable Beach House on LI Sound

JordanRating, 5 stars2 weeks ago
Had an excellent stay at Eileen’s place. The house was extremely clean and perfect size for a couple. Beautiful view and surroundings. Only wish I had more time to explore the area. Would definitely stay here again if I return.
Top guest favourite
Home in Milford
5 out of 5 average rating, 28 reviews

Bull Shark Bungalow-Walk to Beach, Pet Friendly

TeresaRating, 5 stars2 weeks ago
Steven’s place was fantastic! He was extremely responsive and flexible with both check-in and check-out, which was so helpful while traveling with kids. We stayed over Memorial Day weekend with our two small children and a dog, and his home was incredibly accommodating. The large backyard with a fire pit was perfect for making s’mores and spending evenings outside. The place was spotless - clean and tidy in every way. It was a wonderful stay for the whole family, and we’d happily come back again.
Top guest favourite
Home in Lordship
5 out of 5 average rating, 7 reviews

Akasa Ocean Front Oasis- Seasonal Pool, Grill

MariaRating, 5 stars1 month ago
Beautiful and spacious home. If you want to relax , this is the house to do it. Beautiful views. The house has was much larger than I expected which explained why the cleaning fee was higher than usual. Host was very nice and accommodating. The house was well supplied with amenities.
Top guest favourite
Home in Milford
5 out of 5 average rating, 89 reviews

HGTV renovation! Steps to shops & water | Firepit!

SandraRating, 5 stars1 week ago
Beautiful home close to ocean boardwalk. Lovely kitchen and yard.
Guest favourite
Home in Milford
5 out of 5 average rating, 8 reviews

New build! 1 house from beach

MartinRating, 5 stars3 weeks ago
Immaculate, beautiful comfortable home on beach block with beautiful water views. Adriana and Robert were amazing, gracious hosts and couldn’t have been more responsive. Among our best Airbnb rentals ever!
Superhost
Home in Norwalk
5 out of 5 average rating, 3 reviews

Private WHOLE HOUSE + Fenced Backyard+ Parking 4br

JackieRating, 5 stars1 week ago
Andrea’s place is very clean, has everything we need. Beds are comfortable, kitchen and dining room are very nice. Our kids enjoyed the playground in the backyard so much. Andrea is always responsive. Thank you!
Superhost
Home in Westport
4.67 out of 5 average rating, 3 reviews

Boho Chic Private Home in the Heart of Westport CT

ClaudiaRating, 5 stars3 weeks ago
Emma and Nick were so welcoming. The entire property has an amazing vibe and peaceful surroundings. The kitchen had all the basics needed. The rooms were very comfortable. You felt like you were in the country but we were a short drive to everything. The entire area was just very charming. Emma and Nick deserve a super host rating for sure.
Top guest favourite
Home in Milford
4.97 out of 5 average rating, 37 reviews

Modern Beach Mood!

ElizabethRating, 5 stars4 weeks ago
Great spot in a great location! Cole was flexible and communicative. Would love to stay again next time I’m in Milford!

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

Destinations to explore