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.

48 Wellner Dr
	48 Wellner Dr Fairfield, CT $3,500 Vacation Rentals, Unknown  NEW! 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
	155 Halley Ave Fairfield, 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
	516 Oldfield Rd Fairfield, 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
	39 1st St Fairfield, 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
	12 Sandy Way Fairfield, 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
	86 Benson Pl Fairfield, 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
	Roseville Ter Fairfield, 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
	140 College Pl Fairfield, 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
	1410 Post Rd Fairfield, 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
	775 Sasco Hill Rd Fairfield, 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
	56 Bibbins Ave Fairfield, 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
	236 Sterling St Fairfield, 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
	186 Schiller Rd Fairfield, 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
	770 Reef Rd Fairfield, 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
	218 Verna Hill Rd Fairfield, 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
	345 Old Dam Rd Fairfield, 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
	1025 Reef Rd Fairfield, 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
	2131 Fairfield Beach Rd Fairfield, 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
	1018 Reef Rd Fairfield, 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
	22 Oldfield Dr Fairfield, 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
	10 Ann St Fairfield, 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
	775 Sasco Hill Rd Fairfield, 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
	26 Finn St Fairfield, 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
	76 Blaine St Fairfield, 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
	91 Dill Rd Fairfield, 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
	1139 Old Academy Rd Fairfield, 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
	128 College Pl Fairfield, 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
	1109 Reef Rd Fairfield, 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
	271 Henderson Rd Fairfield, 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
	2063 Fairfield Beach Rd Fairfield, 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......

539 Knapps Hwy
	539 Knapps Hwy Fairfield, CT $2,625 Vacation Rentals, Unknown FAIRFIELD SINGLE FAMILY 2 BR 1 BA(NEWLY RENOVATED) - A newly renovated bright and airy single family 2 bed and 1 bath rental is ready for move in April 1! Treat this single family as your own. A......

56 Eleanor Ter
	56 Eleanor Ter Fairfield, CT $3,700 Vacation Rentals, Unknown Adorable beach area two bedroom bungalow on a quaint dead-end street, walking distance to marina, beach and downtown stores and restaurants. Freshly painted interior with hardwood floors......

156 Bungalow Ave
	156 Bungalow Ave Fairfield, CT $6,000 Vacation Rentals, Unknown Charming home in downtown Fairfield on quiet neighborhood street. Well maintained and freshly painted. Walk to everything including restaurants, French bakery, shops, beach and Fairfield train......

51 Geneva Ter
	51 Geneva Ter Fairfield, CT $6,600 Vacation Rentals, Unknown Fairfield beach area cozy retreat. Fully furnished 6 bedrooms and 2 Baths. Bright and breezy beach cottage, walk to South Pine Creek beach, golf course or Fairfield indoor/outdoor tennis club.......

148 Youngstown Rd
	148 Youngstown Rd Fairfield, CT $4,000 Vacation Rentals, Unknown A must see! Pristine, lovely, updated 3 Bed Room, 2 Bath home. Eat in kitchen with Granite Countertops and wood floor, 3 Season Porch off kitchen. Bay window in Living room. Living room and......

206 Pine Creek Ave
	206 Pine Creek Ave Fairfield, CT $16 Vacation Rentals, Unknown Direct waterfront with huge deck. Fully furnished, air-conditioned beach bungalow in quiet neighborhood. House has back and front porches, vaulted ceiling main room upstairs and three bedrooms......

997 Fairfield Beach Rd
	997 Fairfield Beach Rd Fairfield, CT $20 Vacation Rentals, Unknown "Sweet Water," is a beautiful beach front property with beach access and parking on site. The views from the master bedroom overlook the water....

934 Fairfield Beach Rd
	934 Fairfield Beach Rd Fairfield, CT $4,900 Vacation Rentals, Unknown Welcome to "The Upper Deck". An ideal location on Fairfield Beach. Single family home. Available for summer rental. Fully Furnished. Hardwood floors Back Upper Deck with Grill 4 Bedroom (3 Full/1......

999 Oldfield Rd
	999 Oldfield Rd Fairfield, CT $5,000 Vacation Rentals, Unknown - 3 Bedroom 1 Bath Furnished House - 1369 SQFT - Sunny and bright - Hardwood floors - 8 foot ceilings with crown moulding - Fireplace - Eat-in kitchen - Washer & Dryer - Sunroom off the kitchen -......

2123 Fairfield Beach Rd
	2123 Fairfield Beach Rd Fairfield, CT $19 Vacation Rentals, Unknown Brand new rental opportunity! Gorgeous and spacious fully furnished home directly on Fairfield Beach with a beautiful private beach and water views everywhere!! Multiple home offices suited well......