Holiday rentals in Fairfield

4.9 out of 5 average rating, 118 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bath Exclusive Driveway Parking spots➕Private Main Entrance, separate from full-time renters on 1st FL using back entries Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

4.95 out of 5 average rating, 210 reviews

Guest suite in Fairfield

2 BRm Suite; Ktchn; Livng area; wash/dryr; Private

Fully accessorized, large (919 sq ft) beautiful suburban space with bedroom (queen); convertible Murphy bed (queen), in-room sitting area/large screen TV, kitchenette; 2nd room: bedroom (queen) with living space / large screen TV; private full bath; in-suite washer/dryer; private entry to suite (front door; up 1 flight of stairs). Includes light continental breakfast. Owners on property. Off street parking. Train station a mile away (NYC: 70 min). 2 miles to beach. Easy walk to Fairfield U.

4.92 out of 5 average rating, 115 reviews

Downtown Fairfield 3 bedroom Colonial

Enjoy a charming, 3 bed/2 full bath Colonial that is only a 4 block walk from the coffee shops, bars, and restaurants on the Post Road and .7 mile from the Fairfield Train Station. The house is over 1500 sq. feet on a quiet street and only a mile to the town beaches. Work has taken me from Fairfield, but it remains home, so the house is fully stocked with everything. If you're into shooting hoops, you'll like the lined and paved court. Small well-trained dogs and longer stays are negotiable.

4.94 out of 5 average rating, 167 reviews

Guest suite in Fairfield

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

4.97 out of 5 average rating, 30 reviews

Once a Pond - time and stress slow down.

If you're looking for a place to escape the City, gather family, work on a book writing project, just breathe, go to the beach or let your dog run, this is the perfect place! The house sits on 4 acres full of wildlife and free of highway noise with a 2 acre pond centrally located in the University area of Fairfield, relatively close to the train station, downtown and the beach. If you need a car for your stay, you can also rent from us via Turo. Looking forward having you as our guest! :)

4.97 out of 5 average rating, 127 reviews

Guest house in Wilton

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

5 out of 5 average rating, 49 reviews

5 Minute Walk to Beach & Downtown Fairfield

This Immaculate 3-bedroom cape in the desirable Fairfield Beach Area is only a 5 minute walk to the sand. The home has just been beautifully updated and has all modern amenities. Start your day in the breakfast nook which overlooks the lovely level fenced in backyard and enjoy an evening cocktail on the deck. Close enough to the train and downtown to walk and take a stroll to the Marina in the evening. The location is just perfect and the house is a wonderful place to relax and recharge.

5 out of 5 average rating, 111 reviews

Peaceful Suburban Colonial w/New Kitchen.

Looking for a clean, cozy, secluded suburban escape that's still close to great shopping, Long Island Sound, and the two Fairfield Universities? Look no further than this newly renovated colonial on a quiet tree-lined street with no through traffic. A park and basketball are just at the end of the street. Trader Joes and other great shopping are a 2 minute drive away. Sacred Heart and Fairfield U are 5 minutes away. We're right across the street in case any of us forgot anything :).

4.97 out of 5 average rating, 153 reviews

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.95 out of 5 average rating, 332 reviews

Cottage in Milford

Summer Sale|CozyCottage|Pet-friendly|Walk to Beach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

5 out of 5 average rating, 15 reviews

Stareway to Heaven

Welcome to your ideal beachside retreat in Fairfield, CT. This fully furnished 4-bedroom, 3 1/2 bath home offers an open-concept living space, a chef’s kitchen, and a private rooftop deck with stunning coastal views. Just steps from the beach and close to downtown shops and dining, it provides the perfect blend of luxury and convenience. Optional beach cruiser rentals and paddleboards are available. Flexible rental terms are offered for both short- and long-term stays.