Holiday houses in Ridgefield

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Top-rated holiday rentals in Ridgefield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A serene view from the covered porch showcases a lush green lawn leading to the tranquil waters of Henderson Pond. Tall trees frame the scene, with dappled sunlight filtering through the leaves, creating a calm and inviting atmosphere.
Guest suite in Wilton
4.92 out of 5 average rating, 167 reviews

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Top Guest favourite
A wooden porch is visible, featuring two black chairs and an orange table. Potted flowers add color on either side, with a stone pathway leading into the surrounding greenery. The gray siding of the building complements the outdoor seating area.
Apartment in Redding
4.94 out of 5 average rating, 500 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your SPRING holiday at the Huckleberry Quarters, a beautifully appointed studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy any season, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Top Guest favourite
Home in Wilton
4.97 out of 5 average rating, 145 reviews

The Cozy Little Cottage

Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our 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. We have a twin air mattress for use in the living room.

Top Guest favourite
A cottage nestled in a lush green setting is highlighted, surrounded by trees. The lawn is spacious and well-maintained, featuring a hammock between two trees. The structure showcases a simple facade with light blue siding, white window frames, and a chimney.
Home in Newtown
4.99 out of 5 average rating, 127 reviews

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 428 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Guest favourite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guesthouse in Waccabuc
4.98 out of 5 average rating, 126 reviews

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Top Guest favourite
A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.
Home in Pound Ridge
5 out of 5 average rating, 180 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Top Guest favourite
An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.
Barn in Bethel
4.98 out of 5 average rating, 257 reviews

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Guest favourite
A bright sitting room features a cozy sofa adorned with colorful pillows. A wooden sideboard stands against the wall, while a small side table holds reading materials. Natural light filters in through two windows, illuminating the room's warm, wooden flooring and vibrant area rug.
Guesthouse in South Salem
4.93 out of 5 average rating, 321 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds, 1 sofa bed ) totally self contained apt,with totally seperate entrance includes a sitting room, bathroom ,mud room and full eat in kitchen,over 2 floors.Located in one end of Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

Top Guest favourite
The cottage is nestled among lush greenery, with a sloping yard leading to a rock bed. Large trees partially shade the structure, which features a combination of dark shingles and white trim. Windows allow soft light to illuminate the interior, enhancing the tranquil surroundings.
Cottage in Danbury
4.97 out of 5 average rating, 170 reviews

Fern Grove Cottage

If you’re looking for tranquility, this is the place for you! This charming cottage is located on a secluded country road. The cottage sits at the back of a gorgeous park-like property, and is near parks with hiking trails. This antique cottage has many modern renovations, providing convenience and comfort while maintaining the historic charm. This is the perfect getaway!

Top Guest favourite
A comfortable outdoor seating area features two wooden lounge chairs beneath a yellow umbrella, overlooking a gentle cascade of water. Lush greenery surrounds the space, enhancing the serene atmosphere, while the sound of the flowing brook adds to the tranquil experience.
Cabin in Redding
4.98 out of 5 average rating, 109 reviews

The Zen Cabin

Seated beside a playful cascade on Moffit’s Brook, this 1960 Log Cabin has been mindfully rejuvenated. 62 miles from NYC, The Zen Cabin offers respite from the hustle and bustle. Skylights, windows, and doors connect you with nature. Media-free, pet-free, and shoe-free. This laid-back retreat resides in one of Connecticut’s most bucolic and protected villages.

Top Guest favourite
The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.
Guesthouse in Brewster
4.99 out of 5 average rating, 325 reviews

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

Popular amenities for Ridgefield holiday rentals

When is the best time to visit Ridgefield?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Ridgefield?

    Ridgefield has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Ridgefield?

    Experience the best of Ridgefield with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Ridgefield?

    Four-legged friends are welcome in Ridgefield. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Ridgefield?

    Yes! Work meets play with ease at over 30 vacation rentals in Ridgefield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Ridgefield house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Ridgefield, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Ridgefield have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Ridgefield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ridgefield have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Ridgefield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ridgefield have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Ridgefield. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in Ridgefield have free parking?

    Absolutely! We offer over 10 boutique hotel rentals with free parking in Ridgefield. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Ridgefield?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with free parking, over 30 homes with air conditioning, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Ridgefield

  • Total holiday rentals

    Explore 60 holiday rentals in Ridgefield

  • Nightly prices starting at

    Ridgefield holiday rentals start at $71 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,430 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Ridgefield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Ridgefield rentals

  • 4.9 Average rating

    Ridgefield stays are highly rated by guests—averaging 4.9 out of 5!