
House holiday rentals in Fairfield
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Top-rated house rentals in Fairfield
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Popular amenities for Fairfield house rentals
House rentals with a pool

Private Hudson Valley Country Retreat
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

Akasa Ocean Front Oasis- Seasonal Pool, Grill
Amazing time front of the ocean, enjoying time with kids and familly. The pool seems great but was too cold for us in this early time of the year.

Pool House
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!

Garden Level Suite with Beautiful Pool
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!

Midcentury Modern ZenHouse Sculptor Studio
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.

Spacious 4 bedroom, oasis with ocean views galore
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!

Meeker Hill House - Country Escape w/ Heated Pool
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

Port Jefferson Convenient, Cozy and Chic!
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.
Weekly house rentals

The Elijah Sterling House
First - the host is beyond amazing- communication, warmth, welcoming. Second, the house is commodious, spotlessly clean, impressively stocked with everything! Fantastic location. And finally, the HOST- the angel host that you need for relaxing when in the area. I honestly can’t say enough good words for all that Rose offered. Sigh … 🤩 pure perfection!!

Historic Designer City Getaway
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.

HGTV renovation! Steps to shops & water | Firepit!
We had a great stay! Home was clean and as described. Host was responsive and very helpful during our stay. Would highly recommend

Oceanfront Retreat: Modern Beach House
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!!

Coastal Lifestyle
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!

Modern Beach Mood!
Great spot in a great location! Cole was flexible and communicative. Would love to stay again next time I’m in Milford!

Charming Brooklawn Hideaway: Ideal Family Stay
We enjoyed our stay. The place was clean, easy to get to, and had comfortable beds and furniture. Great place to stay near Sacred Heart University.

Cozy, updated single family in Fairfield County
Beautiful home would definitely rent again and recommend to family and friends. Thanks Jennifer.
Private house rentals

Adorable Beach House on LI Sound
We had a wonderful stay at Eileen’s place. Many great restaurants close by…Lenny’s, Dockside and Rosso Vino we enjoyed. Delicious ice cream spots..Bishop’s Orchard Creamery and Ashley’s.

Bull Shark Bungalow-Walk to Beach, Pet Friendly
It was a great place to relax and enjoy the peace. Lots to do and the beach was so close. Nice town and friendly people🤗👍.

New build! 1 house from beach
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!

Lakeview Estate - Chef's Kitchen - NYC Getaway
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!

Lavish retreat near downtown
we love the place, Natalie was always communicative and helpful. well equipped the apartment definitely 100% recommended to anyone.

QC Beach
Kristine’s place was absolutely wonderful! Great location and house was fully stocked with everything you needed.

Boho Chic Private Home in the Heart of Westport CT
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.

Grand Fairfield Getaway- 5BR Fam-Friendly near I95
Used this place to visit our daughter at FFU for her senior lax game. Close and way drive
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
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Gilgo Beach
- United Nations Headquarters
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art