Best Vacation Homes in Fairfield County
House
4 Bedrooms
2 Baths
9 Guests
1500 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $582/Night
7 Nights - US $4,071
Apartment
10.0(4 Reviews)
2 Bedrooms
1 Bath
5 Guests
1001.04 ft²
- Fireplace/Heating
View
Parking
Air Conditioner
US $315/Night
7 Nights - US $2,208
Cabin
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $506/Night
7 Nights - US $3,539
New
Apartment
3 Bedrooms
2 Baths
6 Guests
1100 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $479/Night
7 Nights - US $3,354
House
10.0(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
2195.84 ft²
Oceanfront
Skiing- Fireplace/Heating
- Ocean View
US $509/Night
7 Nights - US $3,566
New
Apartment
1 Bedroom
1 Bath
3 Guests
721 ft²
- Fireplace/Heating
Pool- Pet Friendly
- Kitchen
US $396/Night
7 Nights - US $2,769
New
Apartment
1 Bedroom
1 Bath
3 Guests
817 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $371/Night
7 Nights - US $2,596
New
Apartment
2 Bedrooms
2 Baths
5 Guests
1039 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $364/Night
7 Nights - US $2,547
Fairfield County Luxury Rentals
Other
10.0(4 Reviews)
9 Bedrooms
6 Baths
24 Guests
20000 ft²
Hot Tub- Fireplace/Heating
- Pool
- Kitchen
US $5,223/Night
7 Nights - US $36,562
House
10.0(5 Reviews)
6 Bedrooms
6 Baths
11 Guests
7000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $4,652/Night
7 Nights - US $32,562
US $4,140/Night
7 Nights - US $28,980
House
10 Bedrooms
8 Baths
10 Guests
7000 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $3,968/Night
7 Nights - US $27,773
House
10.0(4 Reviews)
5 Bedrooms
7 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $3,741/Night
7 Nights - US $26,190
House
10.0(27 Reviews)
7 Bedrooms
8 Baths
16 Guests
6000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $3,674/Night
7 Nights - US $25,717
House
7 Bedrooms
8 Baths
17 Guests
9999.67 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
US $2,995/Night
7 Nights - US $20,965
House
5 Bedrooms
6 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $2,913/Night
7 Nights - US $20,392
Fairfield County Pet Friendly Vacation Rentals
New
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $289/Night
7 Nights - US $2,026
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
12 Guests
3778.13 ft²
- Hot Tub
- Balcony/Terrace
- Pet Friendly
- Parking
US $810/Night
7 Nights - US $5,670
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $583/Night
7 Nights - US $4,084
New
Apartment
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $185/Night
7 Nights - US $1,294
House
10.0(2 Reviews)
5 Bedrooms
2 Baths
8 Guests
2002.09 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $199/Night
7 Nights - US $1,393
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $179/Night
7 Nights - US $1,254
House
10.0(119 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $143/Night
7 Nights - US $998
Apartment
10.0(79 Reviews)
1 Bedroom
1 Bath
3 Guests
872 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $244/Night
7 Nights - US $1,709
Fairfield County Large Vacation Homes
House
10.0(110 Reviews)
4 Bedrooms
4 Baths
10 Guests
3800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $735/Night
7 Nights - US $5,144
House
10.0(1 Review)
5 Bedrooms
2 Baths
8 Guests
2400.35 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $249/Night
7 Nights - US $1,743
House
10.0(83 Reviews)
6 Bedrooms
3 Baths
12 Guests
6100 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $2,147/Night
7 Nights - US $15,027
Apartment
9.3(4 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $543/Night
7 Nights - US $3,799
House
10.0(41 Reviews)
6 Bedrooms
5 Baths
10 Guests
4500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,744/Night
7 Nights - US $12,209
House
10.0(32 Reviews)
3 Bedrooms
3 Baths
10 Guests
3300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $742/Night
7 Nights - US $5,192
House
10.0(22 Reviews)
5 Bedrooms
5 Baths
12 Guests
5000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,034/Night
7 Nights - US $14,238
House
10.0(20 Reviews)
4 Bedrooms
3 Baths
13 Guests
4400 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,616/Night
7 Nights - US $18,314
Why Choose Rent By Owner for your Fairfield County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Fairfield County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here ensures you experience the best of what this region has to offer, whether you're seeking vibrant local events or peaceful moments in your vacation rentals.
Peak Season Highlights
Spring (March to May)
During this time, the area experiences a burst of natural beauty as flowers bloom and temperatures rise, making it an ideal period for exploring outdoor activities in your vacation rentals.
Average Temperature Daytime: 60-70°F - Nighttime: 45-55°F
Fall (September to November)
The region's vibrant foliage creates a picturesque backdrop, attracting visitors who prefer to enjoy crisp air and scenic surroundings from their vacation rentals.
Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
Off-Season Highlights
Winter (December to February)
Cold weather and fewer tourists characterize this season, offering a peaceful retreat from the crowds while still providing cozy accommodations for winter enthusiasts.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Summer (June to August)
While summer can be lively, it’s also when the area sees lower occupancy outside peak months, allowing you to enjoy more private and relaxed stays in your vacation rentals.
Average Temperature Daytime: 80-85°F - Nighttime: 60-65°F
Weekly Weather Forecast for Fairfield County
How to Book Your Fairfield County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Fairfield County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a fully equipped patio or barbecue area.
- Relax by a private swimming pool or hot tub, perfect for unwinding after exploring the region.
- Take advantage of expansive lawns or gardens ideal for outdoor activities and gatherings.
- Benefit from scenic walking or jogging trails directly accessible from your rental.
- Make use of outdoor fireplaces or fire pits for cozy evenings under the stars.
- Utilize spacious decks or verandas that offer beautiful views of the surrounding landscape.
- Engage in recreational sports with access to tennis courts, volleyball nets, or other outdoor amenities nearby.
Top Attractions Around Fairfield County
What attractions are nearby?
Here, you can explore a variety of outdoor activities and cultural attractions that showcase the best of this region’s natural beauty and local heritage while enjoying your stay in nearby vacation rentals.
Family Activities
- Stepping Stones Museum for Children: Engage with interactive exhibits designed to inspire learning and creativity for kids of all ages within the region.
- Connecticut Audubon Society Birdcraft Museum and Sanctuary: Explore family-friendly walking trails and observe local bird species in a peaceful natural setting nearby.
- The Maritime Aquarium at Norwalk: Discover marine life through hands-on exhibits and captivating animal encounters, perfect for family outings here.
- Connecticut Botanical Center: Enjoy outdoor exploration and educational programs amidst beautifully maintained gardens that make for a lovely day with your loved ones.
Adult Activities
- Wine Tasting Tours: Explore local vineyards and indulge in wine tasting experiences that highlight the region's renowned viticulture.
- Golfing: Enjoy a round of golf at some of the area's scenic courses, offering stunning views and challenging layouts for enthusiasts.
- Historic Site Visits: Discover the rich history of this destination by visiting historic landmarks and museums that tell the story of the region.
- Fine Dining: Savor exquisite culinary offerings at upscale restaurants emphasizing farm-to-table cuisine native to here’s vibrant food scene.
Other Places to Stay in Fairfield County, CT
Gold Coast
Stamford
Danbury
Downtown
Bridgeport
Fairfield
Main Street Historic District
Norwalk
Westport
Greenwich
Stratford
New Fairfield
Fairfield County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy the area's attractions with more tranquility and better availability for your preferred vacation rentals.
- Explore Local Cuisine and Dining Options: Tasting authentic regional flavors enhances your experience, and many rental properties are conveniently located near top local restaurants.
- Take Advantage of Water Activities and Outdoor Recreation: The region offers a variety of outdoor pursuits that can be easily accessed from your rental, providing memorable adventures amidst natural beauty.
- Utilize Smart Booking Strategies: Securing your vacation rentals early ensures better choices and competitive rates, allowing you to maximize your stay here with confidence.
Transportation Options
- Metro-North Railroad: You can easily access commuter rail services connecting to New York City and other parts of the region, making it convenient for day trips or commuting.
- Connecticut Post Road (Route 1): This major highway offers straightforward driving options through the area, linking you to neighboring towns and local attractions.
- Bradley International Airport: A primary airport serving the area, providing domestic flights that simplify travel both nationally and internationally.
- Local Bus Services: Several regional bus operators offer routes around the destination, perfect for exploring nearby communities without needing a car.
Local Customs Options
- Welcoming Hospitality: You’ll notice a warm and friendly approach from locals, reflecting the region's tradition of hospitality that makes visitors feel at home.
- Seasonal Celebrations: Participating in seasonal festivals and events is common here, offering you an authentic taste of local customs throughout the year.
- Community Gatherings: Local community events often center around neighborhood gatherings and farmers' markets, inviting you to engage with residents easily.
- Respect for Tradition: The area's residents value and preserve their historical customs, which you can observe through various cultural practices and local craftsmanship.
Fairfield County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Fairfield County?
There are a lot of options in Fairfield County. If you plan on staying in the Fairfield County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Fairfield County:
- Lower Lvl Private 2BR/1BA Family/Pet Friendly
- Bright Stylish Chic 4BR 4BA Home Pet Friendly!
- Enjoy our 3-story, family-friendly Carriage House Fireplace and outdoor fire pit
- Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio.more!
- Studio Flat Above Historic Cider Mill
- Candlewood Lakefront 3bd/2 bath house w/180 degree views!
- Make lifelong memories at this New England Quintessential Country Getaway
- Quaint duplex with private yard. Walk to beach, dining, & shopping!
- Private French Country Estate-New Canaan CT-Pool-Film Set-August available
- Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
2. How many vacation rentals have private pools in Fairfield County?
There are 107 vacation rentals with private pools near Fairfield County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Fairfield County are best for families?
If you are looking for a family-friendly vacation home in Fairfield County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Fairfield County:
4. How many Rentbyowner vacation rentals are available in Fairfield County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1323 in the Fairfield County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Fairfield County.
5. What is the cancellation policy for booking a vacation rental in Fairfield County?
Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the options and any applicable fees.
6. How do I find the best vacation rental deals in the region?
To secure the best deals, compare different listings, check for special offers or discounts, and read reviews to ensure quality and value for your stay.
7. Are there any restrictions on bringing pets to vacation rentals here?
Pet policies are set by individual hosts, so it’s important to read each listing carefully or speak with the owner to confirm if pets are allowed during your visit.
8. What amenities can I expect from vacation rentals in this destination?
Amenities vary across properties, so review each listing’s features such as Wi-Fi, parking, kitchens, and outdoor spaces to find the best fit for your needs.
9. How do I ensure my booking is secure and reliable in this area?
Book only through reputable platforms that offer secure payment options and verified listings to ensure a trustworthy and seamless reservation process.
Fairfield County Top Rated Vacation Rentals
House
10.0(89 Reviews)
3 Bedrooms
1 Bath
7 Guests
3800 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $637/Night
7 Nights - US $4,460
Apartment
10.0(37 Reviews)
3 Bedrooms
2 Baths
6 Guests
1000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $369/Night
7 Nights - US $2,582
House
10.0(28 Reviews)
1 Bedroom
2 Baths
2 Guests
1000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $546/Night
7 Nights - US $3,824
House
10.0(23 Reviews)
6 Bedrooms
4 Baths
14 Guests
4200 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,806/Night
7 Nights - US $12,639
House
10.0(21 Reviews)
1 Bedroom
2 Baths
2 Guests
1000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $593/Night
7 Nights - US $4,153
House
10.0(20 Reviews)
3 Bedrooms
1 Bath
5 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $470/Night
7 Nights - US $3,287
House
10.0(19 Reviews)
7 Bedrooms
6 Baths
18 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,185/Night
7 Nights - US $15,295
Cottage
10.0(19 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $380/Night
7 Nights - US $2,660
