Plan your trip

A marina with multiple sailboats docked at sunset.

Fairfield Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

  • Check prices for these dates

    Check prices for these dates, December 13 – 14, 2026

    View in a map

    Our top choices for Fairfield vacation rentals

    1. DUNE Fairfield Beach

    A rocky beach at sunset with calm water and a clear sky.

    2. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

    A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

    3. Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

    A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

    4. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

    A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

    5. Stareway to Heaven in Fairfield

    A modern kitchen with a large island, wooden cabinets, and pendant lighting.

    6. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

    A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

    7. Stareway to Heaven Su

    A modern kitchen with a large island, wooden cabinets, and pendant lighting.

    8. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

    A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

    9. 4 Mi to Beach & Dtwn! Charming Fairfield Home

    A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

    10. 4 Mi to Beach & Dtwn! Charming Fairfield Home

    A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

    11. Spacious Studio with Pool Table

    A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

    12. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

    A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

    13. Business or Weekend escape

    A swimming pool at night with blue lighting.

    14. Renovated 2BR Retreat / Modern Comforts Included

    A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

    15. Modern 2 Bed in BlackRock

    A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

    16. Luxury Designer 2 bedroom+office/3bed vacation home.

    A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

    17. Centric property close to all the great things in the city

    A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

    18. Elite room stay

    A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

    19. The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry

    Private kitchen

    20. Guesthouse at Norwalk Inn

    A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

    View all properties

    Find vacation rentals that suit your style

    Aparthotels

    Apartments

    Cabins

    Cottages

    Condos

    Villas

    Top Fairfield Hotel Reviews

    Delamar Westport

    A buffet bar with various food items and a selection of liquor bottles in the background.

    Delamar Southport

    A restaurant with outdoor seating, a white facade, and a sign reading "ARTISAN".

    Hotel Marcel New Haven, Tapestry Collection By Hilton

    A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.

    The Watershed

    A wooden interior with a reception desk, framed botanical prints, and a sign reading "The Water."

    The Surfside Hotel

    A room with a view of the ocean at sunset, a dining table with plates and glasses, and a wicker chair.

    Residence Inn Stamford Downtown

    The entrance of a Marriott Residence Inn with a revolving door, large windows, and a stone facade.

    The Blake Hotel

    A modern restaurant with a bar area, seating arrangements, and a decorative wall.

    Residence Inn by Marriott Milford

    A spacious living area with a dining table, comfortable seating, and a large window providing natural light.

    Homewood Suites by Hilton Orange New Haven

    A stone building with a covered patio area, outdoor seating, and a fire feature.

    The Study at Yale

    A library with bookshelves, a sofa, a lamp, and decorative items.

    Bedford Post Inn

    A large, two-story house with a covered porch and multiple windows.

    DUNE Fairfield Beach

    A rocky beach at sunset with calm water and a clear sky.

    New Haven Hotel

    A spacious lobby with a sofa, armchairs, and a coffee table. There is a fireplace and a wall-mounted artwork.

    Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

    A modern dining area with multiple tables and chairs, a kitchen area with appliances, and a seating area with a large window.

    Graduate by Hilton New Haven

    A dimly lit bar with wooden furniture, hanging pendant lights, and a bar counter with a neon sign.

    Residence Inn by Marriott Norwalk

    A modern lounge area with a stone fireplace, leather seating, and large windows offering a view of the city.

    The Circle Hotel Fairfield

    A clear blue swimming pool with lounge chairs and umbrellas, surrounded by trees.

    J House Greenwich

    An indoor restaurant with a bar area, seating, and greenery.

    Find out more about Fairfield

    Everything you need to know about Fairfield vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fairfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fairfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Fairfield vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Fairfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Fairfield in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $144 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

    How to find incredible deals on Fairfield rentals

    At Expedia, we put the best Fairfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Fairfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fairfield vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fairfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find vacation rentals in Fairfield?

    Yes, there are vacation rentals in Fairfield close to Fairfield Theater Company, or you can select a more remote option if you'd like a relaxing place to stay. Discover why Fairfield is known for its shops and beaches. While you're here, grab a bite or have a drink at the restaurants.

    What are some of the best vacation home rentals that Fairfield has to offer?

    Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends: Visitors like this Fairfield vacation home rental. It is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

    How many vacation rentals are there in Fairfield?

    With 48 Expedia vacation rentals, you're sure to find just the right place for your Fairfield stay.

    What can I see and do in Fairfield?

    Enjoy the outdoors at Penfield Beach and Fairfield Beach, or simply take in cultural attractions like Fairfield Theater Company and Connecticut Audubon Birdcraft Museum. Jennings Beach and Lake Mohegan are other places to visit while you're in town.

    What are vacation rentals like in Fairfield?

    Vacation rentals are privately owned accommodations you can book for several days or longer in Fairfield. Vacation rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.

    Explore a world of travel with Expedia