Holiday rentals in Caldwell

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Top-rated holiday rentals in Caldwell

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

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Top guest favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
4.99 out of 5 average rating, 126 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Top guest favourite
A cozy seating area features a blue futon sofa and a matching chair with yellow accent pillows. A small coffee table sits on a decorative rug. A lighted lamp and artwork add charm, while a glimpse of the bedroom is visible in the background.
Guest suite in West Orange
4.99 out of 5 average rating, 302 reviews

Lovely Fragrance Free Guest Suite Near NYC

Welcome! I'd love to host you! I have made every effort to insure a clean, cozy stay with lots of amenities The Suite has been remodeled and decorated to create a peaceful space for you to return to after a long day or to work remotely. Spare time-books, games and Alex music. *Entry is not private, it is through the hosts living area* (You will have your own keys and you and are free to come and go as you like) I keep a fragrance free home and require that guests be fragrance free too

Guest favourite
A charming, two-story barn conversion features a blue exterior with yellow accents on the garage doors. A spacious deck overlooks the surrounding greenery. The property is enclosed by trees, providing a serene environment, while a well-maintained lawn enhances the inviting outdoor space.
Barn in West Orange
4.86 out of 5 average rating, 182 reviews

Quaint Converted Barn

Terrific space with loads of light and openness. Overlooking golf course, hayloft converted into king bed with twin bunks in office nook and 1.5 baths. It's the perfect place to get away from it all. Barn converted into residence. Comfy, quiet and serene. First level has living room, dining room and a half bath with a spiral to the hayloft which is open to below and divided by closets that create the office nook but permit light over them. The barn is open, only the bathrooms have doors.

Top guest favourite
Home in Montclair
4.98 out of 5 average rating, 801 reviews

Cozy Cabin Style Apt In Montclair City Center

Must be at least 25 yrs old to book. *This is a quiet space as we live in the apartment below. Absolutely NO parties and a MAX of 2 people in the room at any time. This all wood, 3rd floor studio is right in the center of town. Tons of restaurants, bars, theaters, and super easy NYC transit (Train and Bus) are all just a few min walk away. The apt. is totally open, has a private entrance, private bathroom, amazing decor, parking and lovely touches throughout. ROMANTIC PACKAGES AVAILABLE.

Top guest favourite
A log cabin is nestled among tall trees, showcasing a natural stone foundation. Lush greenery and pink flowers frame the entrance, where stone steps lead up to a wooden deck. Large windows invite natural light into the home, creating a serene woodland setting.
Cabin in Greenwood Lake
4.96 out of 5 average rating, 479 reviews

Cabinessence -on Greenwood Lake, NY #34370

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.98 out of 5 average rating, 383 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Top guest favourite
A quiet front porch features a comfortable seating area with plush cushions. Hanging plants and string lights add a touch of charm. The view includes a tree-lined street, with parked cars visible in the soft glow of evening light.
Flat in Montclair
4.98 out of 5 average rating, 121 reviews

Updated private two bedroom in heart of Montclair

A complimentary bottle of red wine is included with each stay by default. The space is quiet for Montclair yet centrally located. Our cleaner Mikki is responsible for cleaning and preparing the space. She takes great pride in her work, and we’re lucky to have her. The entire cleaning fee goes to her. I travel almost exclusively using AirBnb. If you value a space to be exclusively yours, as I do, this is likely the AirBnb for you. It would be a privilege to host you 🙂. Cheers, Alex

Guest favourite
Home in West Caldwell
4.88 out of 5 average rating, 136 reviews

Carriage House on private historic estate-near nyc

Relax in a 3-bedroom carriage house set on a private historic estate (c. 1752) - appx 20 miles from NYC. Experience this one-of-a-kind “oasis in a metropolis” which blends rustic charm and modern comfort, offers privacy, garden views and a timeless vibe rarely found near NYC. Ideal for corporate travelers, wedding, relocation, family, medical/nurses and tourists: NYC, FIFA World Cup. Walk to food/shops +Free Parking+ dog friendly. Conde Nast Traveler 2025 -Best Airbnb NJ

Top guest favourite
A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.
Home in Greenwood Lake
5 out of 5 average rating, 216 reviews

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Superhost
A light-colored sectional sofa is arranged in a cozy living area, accompanied by a round wooden coffee table. A patterned rug lies beneath, while a potted plant and decorative vase with flowers add a touch of greenery. A world map decorates one wall, enhancing the space's ambiance.
Flat in East Orange
4.89 out of 5 average rating, 131 reviews

The space Gemini 1

Gemini 1 is a cozy space located in a quiet and safe neighborhood. It’s a stylish and comfortable apartment designed to make you feel at home. Perfect for up to 4 guests, with a full kitchen, Wi-Fi, keypad entry, and free parking. Just 8 min walk to the train to 🗽 NYC and 2 min to Watsessing Park. Only 15–17 min drive to ✈️ Newark Airport, 🎢 American Dream Mall, 🏟️ MetLife Stadium, ⚽ Red Bull Arena, and 🏒 Prudential Center. 30–35 min to 🏙️ Times Square

Guest favourite
A bright studio space features a cozy queen bed with a textured blanket, complemented by neutral-toned walls. A small coffee table is positioned in front of the bed, while a TV is mounted on the wall opposite. A kitchenette with cabinetry and a fridge is visible in the background.
Home in West Orange
4.94 out of 5 average rating, 200 reviews

Cute n cozy, minimalist studio

This meticulously curated Japandi-inspired studio is perfect for remote work or a peaceful retreat. The space features a cozy queen bed, small loveseat, and seating area. Enjoy high-speed internet, TV, and a writing desk for productivity. The suite includes a kitchenette with a fridge, microwave, and coffee maker. Located in a quiet, safe neighborhood, with access to a backyard fire pit for relaxation. Ideal for a calm, comfortable, and productive stay.

Guest favourite
Flat in Clifton
4.89 out of 5 average rating, 135 reviews

Luxury 1 Bed | World Cup Homebase

Experience resort-style living in your one-bedroom, one-bathroom apartment in Clifton, perfect for business travelers and short-term stays. The bedroom features a comfortable king bed, plus a full kitchen, living area, and all utilities included. Relax at our resort-style pool, work from our 24/7 business center, and enjoy direct transit to Manhattan, all while being minutes from MetLife Stadium for games, concerts, and FIFA World Cup™ games.

Popular amenities for Caldwell holiday rentals

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