Holiday rentals in Brookfield

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Top-rated holiday rentals in Brookfield

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

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Top guest favourite
Vibrant orange tulips bloom in the foreground, contrasting with lush green foliage. A sign for Studio Holtquist is visible in the background, alongside colorful artistic sculptures standing amidst a bed of pink flowers. The scene is set against a backdrop of trees, indicative of a serene environment.
Home in Woodbury
4.99 out of 5 average rating, 138 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this sanitized, rambling, relaxing, light-filled 2 story 4 bedroom 2.5 bath on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from 5 popular, fabulous restaurants. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."

Top guest favourite
A well-maintained two-story home is surrounded by lush greenery and manicured landscaping. The exterior features symmetrical windows and a red front door that adds a pop of color. A spacious driveway leads toward the entrance, highlighting the serene setting within a forested area.
Home in Brookfield
4.89 out of 5 average rating, 18 reviews

Updated Home In Lake Community

Welcome to the desirable Candlewood Shores community! Our home combines modern amenities with classic charm, creating the perfect sanctuary for relaxation and entertainment. The functional layout ensures a top-notch experience and you can enjoy your morning coffee with a view of Candlewood Lake! Out back you’ll find a deck and patio area, complete with an outdoor fireplace and hot tub! Candlewood Shores community features a beach, boating facilities, playground facilities and ball fields.

Guest favourite
A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.
Cottage in New Milford
4.95 out of 5 average rating, 230 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Top guest favourite
Guest house in Southbury
5 out of 5 average rating, 31 reviews

The Perch in the Purchase

Welcome to The Perch -- Brand new in 2025! Cozy, unique, and private 2nd-floor apartment in a peaceful, rural setting near 84. Nearby hiking trails, boutique shops, charming restaurants, and a local movie theater. Explore nearby Woodbury for antiques and the beautiful and peaceful location. Fully equipped with all you might need -- ideal for relaxing, remote work, or some time away. Safe & quiet -- perfect for short visits or extended stays. Discounts available for longer bookings.

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, 121 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 favourite
A welcoming living area features a green sofa positioned next to large glass doors that open to a view of the outdoor surroundings. A round side table is placed nearby, and natural light fills the space, highlighting the warm wooden walls and floor.
Guest house in New Milford
4.98 out of 5 average rating, 110 reviews

Luxury in the Litchfield Hills

Enjoy this gut-renovated two-floor post-and-beam luxury cottage just outside Kent, CT. Just 9 minutes from downtown Kent and close to the best of Litchfield County, our cottage sits on a serene 3.5 acre property that backs up to protected woodlands. We painstakingly brought the rustic space into the present, with a new kitchenette; bathroom with a massive, spa-like shower; new HVAC; and hotel-like accommodations. Close to Kent School, Canterbury, and great for a romantic getaway.

Top guest favourite
Guest suite in Bethlehem
4.99 out of 5 average rating, 345 reviews

Quiet cottage w/chickens, gardens near Litchfield

Escape to this charming two-story suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, under 30 min to Mohawk and just 90 miles from NYC, you'll have easy access to winter fun!

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, 424 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
Home in Danbury
4.96 out of 5 average rating, 119 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

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.
Flat in Brookfield
4.91 out of 5 average rating, 307 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.

Top guest favourite
Home in Newtown
5 out of 5 average rating, 13 reviews

Charming 1875 Retreat - Walk to Village

Experience the best of Newtown in this 1875 historic estate (renovated 2025). A perfect family getaway, we are a 4-minute walk to Sandy Hook Village dining & shops. Unlike shared rentals, enjoy a private single-family home with soaring 9 ft ceilings, quiet Central A/C, and Wired Gigabit Internet. Cook in the large kitchen, relax on the patio, or sleep deeply on premium mattresses. Steps from the Pootatuck River trails!

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, 254 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.

Popular amenities for Brookfield holiday rentals

When is the best time to visit Brookfield?

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Frequently Asked Questions

  • Do house rentals in Brookfield have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Brookfield. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Brookfield?

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

  • Are there family-friendly vacation rentals in Brookfield?

    Brookfield has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

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

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

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with free parking, over 40 homes with air conditioning, over 30 homes with a kitchen, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Brookfield have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Brookfield. Enjoy a tailored experience with all the comforts you desire.

  • Are there Brookfield vacation rentals on Airbnb with pools?

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

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

    Experience the best of Brookfield with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Brookfield have a kitchen?

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

  • Do house rentals in Brookfield have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Brookfield. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Brookfield

  • Total holiday rentals

    Explore 50 holiday rentals in Brookfield

  • Nightly prices starting at

    Brookfield holiday rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 1,890 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    50 of Brookfield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Brookfield rentals

  • 4.9 Average rating

    Brookfield stays are highly rated by guests – averaging 4.9 out of 5!