Holiday houses in Fairfield

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Top-rated holiday rentals in Fairfield

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Guest favourite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

24–31 Oct

$237 NZD per night

Guest favourite

Home in Fairfield

4.96 out of 5 average rating, 289 reviews

Luxurious Barn With New England Charm

Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.

21–28 Jan

$498 NZD per night

Guest favourite

Apartment in Fairfield

5.0 out of 5 average rating, 51 reviews

Bright, private 1,000 sq. ft. 1-Bedroom Apartment

Wow! 1,000 square foot Rental Suite now available for short or long--term rentals, vacation, University visitation, etc. Clean, bright, spacious and private. Apartment is a second story suite, attached to a separate single-family home and has a separate private entrance. Vaulted ceilings throughout, two sets of large glass sliders leading to deck overlooking 0.5 acre property which abuts Fairfield Town Open Space with lovely creek passing through. Attracts lovely birds! More detail below.

11–18 Oct

$301 NZD per night

Guest favourite

Guest suite in Fairfield

4.93 out of 5 average rating, 110 reviews

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.

24 Nov – 1 Dec

$289 NZD per night

Guest favourite

Apartment in Westport

4.93 out of 5 average rating, 114 reviews

Spacious Westport Apt surrounded by nature

Spacious mother-in-law apartment w/ private entrance on the 1st floor of our beautiful home. Windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8-10 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, and wonderful bakeries and restaurants nearby!

3–10 Nov

$339 NZD per night

Guest favourite

Guesthouse in Norwalk

4.99 out of 5 average rating, 207 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

19–26 May

$235 NZD per night

Guest favourite

Home in Milford

4.98 out of 5 average rating, 152 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

19–26 Nov

$657 NZD per night

Guest favourite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

2–9 May

$310 NZD per night

Guest favourite

Guest suite in Norwalk

4.9 out of 5 average rating, 111 reviews

Efficiency Garden Studio in South Norwalk, CT

Beautiful Efficiency Studio with private entrance in South Norwalk. Self-contained with private bath, kitchenette and off street parking. 10 min walk to South Norwalk Rail Station. 60 minutes to Manhattan, 10 min to historic SoNo. 10 min drive to Stamford. 5 minute drive to Merritt 7 and corporate business district. 5 minute to Norwalk Hospital. 5 min to City Hall. Close to all main arteries. Part of a quaint and charming arts & crafts bungalow, has separate entrance, very quiet.

30 Dec – 6 Jan

$187 NZD per night

Superhost

Loft in Bridgeport

4.86 out of 5 average rating, 173 reviews

Cozy Loft in beautiful St. Mary's by the Sea

Renovated cozy loft in beautiful St. Mary's by The Sea in Black Rock. Walking distance to award winning restaurants. Easy access to NYC/New Haven Metro North transit. Perfect for a weekend at the beach. Property includes 1 bed and a 78” sofa. Fully equipped kitchen with all major appliances, WiFi, & large TV. ***Please note that the ceilings are angled so taller guests (over 5’ 8”) might have to bend in certain parts of the loft.

2–9 May

$323 NZD per night

Guest favourite

Apartment in Fairfield

4.95 out of 5 average rating, 62 reviews

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

14–21 Aug

$304 NZD per night

Guest favourite

Place to stay in Westport

4.96 out of 5 average rating, 278 reviews

Sunny Westport 2 BR Retreat above Historic Mill

This eclectic, sunny, spot, sits above a renovated historic cider mill from the 1850s. It has been designed and furnished by our own team of artisans. With panoramic views and breathtaking surroundings, including endless flora and fauna, and a contingent of mallards, egrets, and swans, this hideaway is the perfect "Get Away."

15–22 Jan

$426 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Fairfield holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Fairfield's top sights

Westfield Trumbull Mall23 locals recommend

Whole Foods Market33 locals recommend

Penfield Beach21 locals recommend

The Warehouse at FTC8 locals recommend

Colony Grill46 locals recommend

Shake Shack6 locals recommend

Other great holiday rentals in Fairfield

Guest favourite

Home in Fairfield

4.91 out of 5 average rating, 67 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

15–22 Jun

$262 NZD per night

Guest favourite

Guest suite in Wilton

5.0 out of 5 average rating, 33 reviews

Guest suite with private enter

7–14 Jul

$177 NZD per night

Guest favourite

Barn in Fairfield

4.95 out of 5 average rating, 40 reviews

Delightfully Renovated Colonial Barn by the Beach!

1–8 May

$711 NZD per night

Superhost

Apartment in Fairfield

4.85 out of 5 average rating, 41 reviews

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

24–31 Jan

$325 NZD per night

Guest favourite

Home in Fairfield

5.0 out of 5 average rating, 10 reviews

Remodeled Cozy Country Cape

1–8 Mar

$684 NZD per night

Guest favourite

Home in Fairfield

5.0 out of 5 average rating, 60 reviews

Fairfield Cottage: Cozy retreat near Universities

22–29 Aug

$872 NZD per night

Guest favourite

Home in Fairfield

5.0 out of 5 average rating, 6 reviews

Stillson House - Central Cozy Updated Colonial

27 Oct – 3 Nov

$580 NZD per night

Superhost

Apartment in Bridgeport

5.0 out of 5 average rating, 5 reviews

Ricport Studio 5

26 May – 2 Jun

$244 NZD per night

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Quick stats about holiday rentals in Fairfield

Total rentals	290 properties
Rentals with dedicated workspaces	160 properties have a dedicated workspace
Rentals with a pool	40 properties have a pool
Pet-friendly rentals	100 properties allow pets
Family-friendly rentals	190 properties are a good fit for families
Total number of reviews	6K reviews

Holiday houses in Fairfield

Top-rated holiday rentals in Fairfield

Guest suite in Fairfield

Home in Fairfield

Apartment in Fairfield

Guest suite in Fairfield

Apartment in Westport

Guesthouse in Norwalk

Home in Milford

Cottage in Easton

Guest suite in Norwalk

Loft in Bridgeport

Apartment in Fairfield

Place to stay in Westport

Holiday rentals for every style

Houses

Apartments

Hotels

Popular amenities for Fairfield holiday rentals

Stay near Fairfield's top sights

Other great holiday rentals in Fairfield

Home in Fairfield

Guest suite in Wilton

Barn in Fairfield

Apartment in Fairfield

Home in Fairfield

Home in Fairfield

Home in Fairfield

Apartment in Bridgeport

Quick stats about holiday rentals in Fairfield

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore