Fairfield, located in the southwestern part of Connecticut, is a picturesque coastal town known for its historic charm and beautiful beaches. The town boasts numerous boutiques, art galleries, and restaurants, making it a popular destination for locals and visitors alike. Fairfield is also home to several top-rated hotels and luxurious residences, offering visitors a comfortable and lavish stay.

Best Choice of Shopping

  1. Fairfield Center: This charming shopping district features a variety of boutiques, jewelry stores, and art galleries, as well as upscale dining options.
  2. The Brick Walk: This outdoor shopping center features a mix of luxury retailers and fine dining options, including J. McLaughlin, Steven Alan, and Terrain Garden Café.
  3. Post Road Plaza: This shopping center is home to a variety of stores, including high-end retailers like Talbots, Chico's, and J. Crew.
  4. Fairfield University Bookstore: Located on the Fairfield University campus, this bookstore offers a unique selection of gifts, clothing, and books.
  5. The Village Green: This outdoor shopping area features a mix of local and national retailers, including Lululemon, Madewell, and Anthropologie.

Most Luxurious Hotels

  1. The Delamar Southport: This luxurious hotel features elegant guest rooms and suites, a full-service spa, and a gourmet restaurant.
  2. The Inn at Longshore: This waterfront hotel features spacious rooms and suites with stunning views of the Long Island Sound, as well as an on-site restaurant and bar.
  3. The Roger Sherman Inn: This historic inn features luxurious guest rooms and suites, a fine dining restaurant, and beautiful gardens.
  4. The Circle Hotel Fairfield: This boutique hotel features stylish guest rooms and suites, an on-site restaurant and bar, and easy access to Fairfield's downtown area.
  5. The Hi-Ho Motel: This retro-chic motel features fun, themed guest rooms and suites, a seasonal outdoor pool, and a lively bar and lounge.

Excellent Dining

  1. Artisan Restaurant: This farm-to-table restaurant features seasonal New American cuisine, craft cocktails, and a stylish dining room.
  2. Paci Restaurant: This cozy Italian restaurant features homemade pasta, fresh seafood, and an extensive wine list.
  3. The Whelk: This trendy seafood spot offers a menu of fresh, locally sourced seafood, oysters, and craft cocktails.
  4. The Chelsea: This waterfront restaurant and bar features stunning views of the Long Island Sound, as well as a menu of creative New American cuisine.
  5. The Gray Goose Café: This cozy café offers a menu of classic American fare, including burgers, sandwiches, and salads, as well as a great selection of craft beers and wines.

World Class Residence

  1. 1353 Pequot Avenue: This stunning waterfront estate features 8 bedrooms, 7 bathrooms, and breathtaking views of the Long Island Sound.
  2. 125 Sasco Hill Road: This elegant estate features 5 bedrooms, 5 bathrooms, and a private pool and tennis court.
  3. 233 Sasco Hill Road: This exquisite colonial-style home features 6 bedrooms, 7 bathrooms, and a pool house with a fireplace and wet bar.
  4. 2745 North Street: This sprawling estate features 7 bedrooms, 10 bathrooms, and a private pool and tennis court.
  5. 9 Willowmere Circle: This stunning lakefront home features 5 bedrooms, 6 bathrooms, and a private dock and boathouse.
short term furnished flexable terms furnished WATERFRONT DUPLEX.
$80,000
Courtesy of Collage Realty
Beach Area Colonial Walk To Beach.
$80,000
Courtesy of Collage Realty
ANY TIME AT THE BEACH ! !
$60,000
Courtesy of William Raveis Real Estate
Welcome to Blue by the Sea, a stunning retreat on the shores of Long Island Sound !
$50,000
Courtesy of William Raveis Real Estate
Surrounded by stone walls, this one of a kind, spectacular and private 36 acre Greenfield Hill country compound has had a stunning top level transformation, creating a breathtaking Fairfield County ...
$39,000
Courtesy of William Pitt Sotheby's Int'l
AVAILABLE JUNE 1, 2025. RENOVATED and ELEGANT Single home peacefully settled in a very private, tranquil and family section of the Penfield Beach.
$20,000
Courtesy of Preoh, LLC
Sophisticated beach front home in premium location rarely available for rent.
$20,000
Courtesy of Compass Connecticut, LLC
Waterfront summer living !
$20,000
Courtesy of Coldwell Banker Realty
Indulge in breathtaking views stretching all the way to New York from this remarkable abode !
$20,000
Courtesy of William Raveis Real Estate
FURNISHED SUMMER RENTAL. Renovated 5 Bedrooms, 2 full baths Home on a Private Large 0.
$15,000
Courtesy of Preoh, LLC
Steps to miles of sandy beaches, breath taking water views, newly remodeled to perfection, and set on an oversized and level.
$13,500
Courtesy of William Raveis Real Estate
Tucked away on a quiet cul de sac, this 8, 000 sq.
$12,500
Courtesy of Farnam Realty Group
Welcome to Yiayia's Beach House !
$12,000
Courtesy of William Pitt Sotheby's Int'l
Location, luxury, and style come together in this beautifully renovated Cape Cod home, ideally located in the highly sought after Fairfield Beach area.
$12,000
Courtesy of William Raveis Real Estate
Spectacular Fairfield Beach Academic Year Rental Available September 1st 2027 May 29th 2028.
$11,500
Courtesy of Berkshire Hathaway NE Prop.
STUNNING IMMACULATE Rental steps from the Beach.
$10,000
Courtesy of Preoh, LLC
STUNNING IMMACULATE Rental steps from the Beach.
$10,000
Courtesy of Preoh, LLC
Exceptional 2 month summer rental June 27 to August 27.
$10,000
Courtesy of Berkshire Hathaway NE Prop.
SUMMER 2025 furnished beach rental available from June 1st to September 1st.
$10,000
Courtesy of William Raveis Real Estate
STUNNING IMMACULATE Rental steps from the Beach.
$9,500
Courtesy of Preoh, LLC
Nestled in the desirable beach area of Fairfield, this beautifully updated Colonial home is a perfect blend of classic charm and modern convenience.
$9,500
Courtesy of William Raveis Real Estate
Quaint Southport location walking distance to the train, library, restaurants and the harbor.
$8,800
Courtesy of William Raveis Real Estate
Stunning Modern Retreat Summer Furnished Home for lease.
$8,800
Courtesy of William Raveis Real Estate
Located in Southport's highly desirable neighborhood, this renovated colonial home on 0.
$7,600
Courtesy of Coldwell Banker Realty
Amazing Beach location plus a fully remodeled home awaits Welcome Home to 170 Longdean Road.
$7,500
Courtesy of William Raveis Real Estate
2025 SUMMER FURNISHED JUNE AUGUST.
$7,500
Courtesy of William Raveis Real Estate
Weekly Summer Rental 6 Nights, 7 Days.
$7,500
Courtesy of CRT Property Services, LLC
FURNISHED SUMMER RENTAL Welcome to your dream beach escape conveniently located between Faifield Center and the beach.
$7,250
Courtesy of Coldwell Banker Realty
Spend the month of August at desirable Long Island Sound Location !
$6,800
Courtesy of Coldwell Banker Realty
NEW CONSTRUCTION LUXURY RENTAL !
$7,000
Courtesy of Keller Williams Realty
Available 6 1 2025. Rent could increase for summer months depending on contract length.
$6,499
Courtesy of Brown Harris Stevens
Come Experience 2107 North Benson, a versatile property offering exceptional living spaces.
$6,500
Courtesy of Keller Williams Realty
Enjoy life in this two year young building in downtown Fairfield !
$6,650
Courtesy of Higgins Group Bedford Square
Introducing 1047 Reef Road, a desirable and sought after beach area rental that depicts coastal living.
$6,500
Courtesy of William Raveis Real Estate
This spacious 4 bedroom, 2.
$6,075
Courtesy of Keller Williams Prestige Prop.
A Jewel of a Beach house, situated in a prime location just 2 doors from Jennings Beach and South Benson Marina.
$6,000
Courtesy of William Raveis Real Estate
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