Vacation rentals in Ridgefield

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Top-rated vacation rentals in Ridgefield

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

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Top guest favorite
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
4.91 out of 5 average rating, 164 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…

Guest favorite
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, 493 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

It’s time to book your Winter 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 favorite
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, 116 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.

Top guest favorite
A tranquil lakeside scene at sunset features vibrant pink and orange hues reflected on the calm water. Silhouetted trees line the shore, and rolling mountains rise in the distance, creating a serene backdrop.
Cottage in South Salem
4.96 out of 5 average rating, 138 reviews

Serene lake front cottage 1 hour from NYC

Serene minimalist cottage directly on Lake Oscaleta with spectacular waterfront and Mountain Lakes Park behind. Quiet, isolated and lost in the trees, you feel you are in Vermont or the Adirondacks. Yet it's only 1 hour from Manhattan, 10 minutes from restaurants. Kayak, canoe, fish, paddleboard. Cottage is elegant, cozy and winterized warm and the lake is effectively empty in the fall/winter/spring. Please note: because of an asthmatic child, we cannot accept any animals.

Top guest favorite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 108 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Superhost
A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.
Apartment in Brookfield
4.92 out of 5 average rating, 296 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest favorite
A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.
Guest suite in Wilton
4.8 out of 5 average rating, 246 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Guest favorite
A quaint cottage is nestled among vibrant trees, showcasing rich foliage in shades of green and burgundy. A well-kept lawn surrounds the cottage, with a white door framed by flower beds. The serene setting invites relaxation in a natural environment.
Cottage in South Salem
4.96 out of 5 average rating, 256 reviews

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

Guest favorite
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, 120 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 favorite
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, 247 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.

Top guest favorite
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
4.98 out of 5 average rating, 165 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 favorite
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
4.99 out of 5 average rating, 107 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.

Popular amenities for Ridgefield vacation rentals

When is the best time to visit Ridgefield?

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Avg. priceG$53,842 GYDG$45,077 GYDG$52,173 GYDG$52,173 GYDG$52,173 GYDG$62,607 GYDG$62,607 GYDG$64,485 GYDG$54,051 GYDG$57,390 GYDG$56,346 GYDG$53,216 GYD
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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.

  • 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.

  • Are there Ridgefield vacation rentals on Airbnb with pools?

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

  • 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.

  • 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 air conditioning?

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

  • 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.

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

    Experience the best of Ridgefield with our boutique hotel rentals, starting at about $250 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Enhance your stay in our Boutique Hotel Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

Quick stats about vacation rentals in Ridgefield

  • Total vacation rentals

    Explore 60 vacation rentals in Ridgefield

  • Nightly prices starting at

    Ridgefield vacation rentals start at G$10,435 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,440 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Ridgefield vacation 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!