Search for vacation rentals in Fairfield.
Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Fairfield area to find the perfect spot for your vacay.
1748 Stratfield Rd |
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1748 Stratfield RdFairfield, CT$6,000
Vacation Rentals, Unknown NEW!
Stunning four bed/ two bath cape with over 2,400 square feet remodeled to perfection centrally located in one of the most desirable areas of Connecticut. Feel like your on vacation everyday and...... |
54 Lloyd Dr |
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54 Lloyd DrFairfield, CT$3,895
Vacation Rentals, Unknown
Step into this eye catching beauty at 54 Lloyd Drive! Imagine yourself in this picturesque neighborhood so close to Lake Mohegan and the best of Fairfield. A beautifully retouched & newly renovated...... |
50 Geneva Ter |
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50 Geneva TerFairfield, CT$9,000
Vacation Rentals, Unknown
Bright and breezy beach cottage, 17 min walk to South Pine Creek beach, golf course or Fairfield indoor/outdoor tennis club. Newly renovated, cozy home in a friendly, quiet residential...... |
48 Brookdale Rd |
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48 Brookdale RdFairfield, CT$5,999
Vacation Rentals, Unknown
Renovated and furnished (optional) 3 bedroom, 1.5 bathroom single family home in the Holland Hills section of the University Area in Fairfield. The neighborhood is a very quiet, family friendly...... |
1005 Old Post Rd |
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1005 Old Post RdFairfield, CT$108
Vacation Rentals, Unknown
Enjoy IN-TOWN LIVING at it's very best! Experience all the picturesque Town of Fairfield has to offer from this beautiful home on the historic Old Post Rd. A short walk to the train (no need for a...... |
Granville St |
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Granville StFairfield, CT$3,750
Vacation Rentals, Unknown
COMING SOON... photos will be available once rennovations are complete: Nestled in the heart of a lively neighborhood, this charming 3-bedroom house offers the ideal blend of urban convenience and...... |
288 Birch Rd |
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288 Birch RdFairfield, CT$105
Vacation Rentals, Unknown
THIS IS A FULLY FURNISHED AND EQUIPPED HOME AVAILABLE FOR SHORT-TERM STAYS, 3 MONTH MIN. 288 Birch Road is a beautiful 3 bedroom, 2 bathroom colonial situated in the highly desirable Fairfield...... |
479 S Benson Rd |
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479 S Benson RdFairfield, CT$7,704
Vacation Rentals, Unknown
THIS IS A FULLY FURNISHED AND EQUIPPED HOME AVAILABLE FOR SHORT-TERM STAYS, 3 MONTH MIN. 479 Benson Road is a beautiful 2 bedroom, 1.5 bathroom private home in a duplex community in the highly...... |
710 Beach Rd |
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710 Beach RdFairfield, CT$18
Vacation Rentals, Unknown
Welcome to 710 Beach Road! An escape to your own private paradise this summer with this exquisite Fairfield Beach rental. Just steps from Jennings / Penfield beaches and the picturesque dawn and...... |
1 Meadow Ct |
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1 Meadow CtFairfield, CT$4,000
Vacation Rentals, Unknown
Expanded cape at the end of the cul de sac, walk to train station, beaches, town. Private.... |
48 Wellner Dr |
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48 Wellner DrFairfield, CT$3,500
Vacation Rentals, Unknown
North Stratfield Area The home is 2 minutes from Sacred Heart/5 minutes from Fairfield University. Close to Rt 15 -New Kitchen/Brand New Appliances -Updated Bathroom -Everything is newly painted...... |
155 Halley Ave |
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155 Halley AveFairfield, CT$3,200
Vacation Rentals, Unknown
Welcome to this charming colonial in this prime location in Fairfield. Conveniently located near I-95, this home offers 2 large bedrooms with ample closet space, 2 full bathrooms (one on each...... |
516 Oldfield Rd |
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516 Oldfield RdFairfield, CT$5,600
Vacation Rentals, Unknown
Fully furnished from pots and pans and dishes to beds and desks and dressers. 3 minutes to the beach and 3 minutes to town just down the road from Fairfield University. Kitchen (refrigerator,...... |
39 1st St |
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39 1st StFairfield, CT$2,900
Vacation Rentals, Unknown
Welcome to this charming residence that offers a comfortable and convenient living experience. As you enter, you'll be welcomed by a spacious living room that is perfect for relaxation or hosting...... |
12 Sandy Way |
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12 Sandy WayFairfield, CT$10
Vacation Rentals, Unknown
Welcome to your dream academic/summer rental! This BRAND NEW 2024 spacious and fully furnished beach rental features 2,400 square feet across three floors of living space, six bedrooms, and three...... |
86 Benson Pl |
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86 Benson PlFairfield, CT$8,000
Vacation Rentals, Unknown
Fantastic and spacious nine room, five bedroom, three bathroom colonial with a two car garage - located in one of the most special spots in the coveted Fairfield Beach Neighborhood. Situated at the...... |
Roseville Ter |
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Roseville TerFairfield, CT$4,400
Vacation Rentals, Unknown
Please note that we are hiding the address to protect our current renter's privacy. We will provide it for serious showings. This charming residence is a newly renovated 4-bedroom, 2-bathroom home...... |
140 College Pl |
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140 College PlFairfield, CT$7,500
Vacation Rentals, Unknown
The house is fully furnished. Beautiful 3 bedroom Ranch very close to the beach for summer fun. Two car garage, central air conditioning, totally rebuilt and lifted in 2015,FEMA compliant and...... |
1410 Post Rd |
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1410 Post RdFairfield, CT$3,325
Vacation Rentals, Unknown
Welcome to upscale living in the heart of Fairfield center! This one-bedroom gem offers the epitome of modern living with unparalleled convenience. Step inside and be greeted by a bright and airy...... |
775 Sasco Hill Rd |
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775 Sasco Hill RdFairfield, CT$40
Vacation Rentals, Unknown
We are offering a summer long-term rental special for June/July/August combinations! Book direct or on our AirBNB listing at air bnb dot com slash h slash sascohillparadise Welcome to our newly...... |
56 Bibbins Ave |
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56 Bibbins AveFairfield, CT$6,200
Vacation Rentals, Unknown
Don't miss out on this great Fairfield home. Close to I-95, Black Rock Turnpike, and Post Rd. 4 levels of living space, back yard, and detached garage. Beautiful hardwood floors.... |
236 Sterling St |
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236 Sterling StFairfield, CT$3,500
Vacation Rentals, Unknown
Immaculate 4 bedroom, 2.5 bath dormered cape cod located on a quiet street and conveniently located near schools, shopping, I-95 and train stations. The home was totally renovated four years ago...... |
186 Schiller Rd |
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186 Schiller RdFairfield, CT$6,795
Vacation Rentals, Unknown
Amazing single family home near Sacred Heart University & Merritt Parkway. Fully furnished 4 bedroom house. Newly renovated and modernly decorated. Beautiful white kitchen has all appliances....... |
770 Reef Rd |
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770 Reef RdFairfield, CT$4,500
Vacation Rentals, Unknown
Welcome to 770 Reef Road, a desirable and sought after beach area rental that depicts coastal living. This split level home is nestled in the heart of Fairfield, located perfectly for a quick walk...... |
218 Verna Hill Rd |
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218 Verna Hill RdFairfield, CT$6,200
Vacation Rentals, Unknown
The perfect summer month rental! Nestled in bucolic and convenient lower Greenfield Hill, this timeless and updated home is minutes from town, beach, lake and Greenfield Hill weekend farmer...... |
345 Old Dam Rd |
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345 Old Dam RdFairfield, CT$4,200
Vacation Rentals, Unknown
Amazing opportunity to live a coastal lifestyle all year long in your own cozy cottage. Pull your boat up, kayak, canoe or paddle board off of your private dock in the back yard of this sensational...... |
1025 Reef Rd |
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1025 Reef RdFairfield, CT$9,300
Vacation Rentals, Unknown
- Summer and Academic Year rentals available! -Now taking applications for Fairfield University academic year Sept. 2026-May 2027. $9,300+ utilities. Apply for 26-27 by 3/31/24 and save $400/month....... |
2131 Fairfield Beach Rd |
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2131 Fairfield Beach RdFairfield, CT$18
Vacation Rentals, Unknown
Indulge in breathtaking views stretching all the way to New York from this remarkable abode! Parking is never a concern with the expansive 6-car garage, ensuring ample space for guests. Crafted...... |
1018 Reef Rd |
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1018 Reef RdFairfield, CT$5,900
Vacation Rentals, Unknown
BEST SUMMER RENTAL VALUE ON REEF! Pack your suitcase and step into your home away from home in the heart of Fairfield's vibrant beach neighborhood. Walk to the beach and park. Drive downtown in...... |
22 Oldfield Dr |
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22 Oldfield DrFairfield, CT$8,900
Vacation Rentals, Unknown
PRICE IS FOR ACADEMIC 2026-2027. Luxury rental fully furnished situated south of the Post Rd. between two of the most coveted beaches in Fairfield. Large kitchen with island, GE Cafe appliances and...... |
10 Ann St |
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10 Ann StFairfield, CT$3,800
Vacation Rentals, Unknown
The ideal living experience opportunity for those seeking a coastal lifestyle with urban conveniences! Enjoy the best of both worlds - the tranquility of a beachside community and the vibrant...... |
775 Sasco Hill Rd |
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775 Sasco Hill RdFairfield, CT$425
Vacation Rentals, Unknown
We are offering a summer long-term rental special for June/July/August combinations! Book direct or on our AirBNB listing at air bnb dot com slash h slash sascohillparadise Welcome to our newly...... |
26 Finn St |
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26 Finn StFairfield, CT$3,800
Vacation Rentals, Unknown
Welcome to 26 Finn St, a delightful residence nestled in the heart of Fairfield, Connecticut. This charming 3-bedroom, 2-bathroom home offers a perfect blend of comfort, style, and convenience....... |
76 Blaine St |
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76 Blaine StFairfield, CT$6,500
Vacation Rentals, Unknown
Experience the quintessential coastal lifestyle in this charming cape home, nestled in a picturesque neighborhood. Boasting 2-3 bedrooms & 2 baths, this residence offers versatile space for your...... |
91 Dill Rd |
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91 Dill RdFairfield, CT$4,200
Vacation Rentals, Unknown
MAY 1 RENTAL! Traditional Cape with 3 bedroom/2 bath. Updated Kitchen and Baths. Hardwoods throughout. Living room built in cabinets with ample storage. Finished basement that's great for kids....... |
1139 Old Academy Rd |
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1139 Old Academy RdFairfield, CT$12
Vacation Rentals, Unknown
Welcome to your dream summer retreat in the heart of bucolic Greenfield Hill! This exquisitely updated home offers a unique opportunity to experience serene suburb living while remaining just a...... |
128 College Pl |
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128 College PlFairfield, CT$3,200
Vacation Rentals, Unknown
SUMMER RENTAL ONLY (Not available for any other terms). Available June 1 through August 24th.- Located just steps from the beach, bar, liquor store, deli and restaurant, this is the perfect summer...... |
1109 Reef Rd |
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1109 Reef RdFairfield, CT$3,000
Vacation Rentals, Unknown
SUMMER RENTAL ONLY (Not available for any other terms). Available June 1 through August 24th.- Located just steps from the beach, bar, liquor store, deli and restaurant, this is the perfect summer...... |
271 Henderson Rd |
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271 Henderson RdFairfield, CT$7,000
Vacation Rentals, Unknown
Welcome this beautiful house close to the river, boasting breathtaking views and ample space for comfortable living. This expansive property features a stunning 5-bedroom, 3-bathroom main house,...... |
2063 Fairfield Beach Rd |
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2063 Fairfield Beach RdFairfield, CT$25
Vacation Rentals, Unknown
This gem of a beach house almost sits on top of the Long Island Sound and is one of the last truly "beachy" and beloved homes left, wwith 5 bedrooms which sleeps 6 guests. Options available for...... |