Holiday houses 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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Guest favourite

A charming exterior view of the carriage house is presented, featuring dark-colored siding with bright red windows and door. Potted plants line the front, and a cozy seating area is positioned on the side, surrounded by greenery and sunlight filtering through the trees.

Home in West Caldwell

3 Bedroom Carriage House- private estate-near NYC-

Relax in a 3-bedroom carriage house set on a private historic estate- 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 and natural pond views, and a vintage vibe rarely found near NYC. Guests love to stargaze, relax by nature, birdwatch. Walkable to shops, restaurants, parks, wellness centers, gyms plus. Free Parking (2cars) +dog friendly. Conde Nast Traveler -“Best Airbnb NJ”. A Rare find Top home

LocationFamilyWalkability

4.89 out of 5 average rating, 141 reviews

Top Guest favourite

The exterior of the guest house is showcased, featuring a mix of brick and elegant architecture. A shaded pergola is visible above a seating area, surrounded by manicured landscaping and mature trees. The blue sky provides a vibrant backdrop to this tranquil setting.

Guesthouse in Montclair

Mountaintop Carriage House with Tennis Court

Take it easy at this unique and tranquil getaway nestled in Montclair’s estate section. Spread over two floors, you have plenty of space to relax in this beautifully renovated guest house. Outdoor space includes a spacious patio with a wood burning chiminea. This one of a kind home is located on a 1.2 acre property with views of NYC from the bedroom (!) as well as access to a private Har-Tru tennis court. Tennis rackets and balls available. (Tennis court may not be playable in winter months.)

LocationValueHospitality

4.94 out of 5 average rating, 50 reviews

Top Guest favourite

A comfortable living area is presented with a blue sofa accented by orange cushions and a matching chair. A coffee table sits in front, surrounded by light hardwood flooring. Decorative shelves in the background display books and woven baskets, providing a cozy atmosphere.

Apartment in West Orange

Fragrance Free One Bedroom Oasis -Near NYC/ERW

*Read Entire Listing Before Booking!* **Rate includes Airbnb's 18.5% fee** Escape to a peaceful, fragrance free, stylish garden apartment! This sunny, lower-level oasis is perfect for a remote work retreat or exploring the area. Fully equipped kitchen, workspace, and a serene shared garden. Comfortably accommodates up to 4 guests, in a private bedroom with a queen bed, a sofa bed in a semi-private area and a sofa bed in the livingroom. A clean, cozy, and calming home away from home awaits you!

ValueFamilyTV

4.98 out of 5 average rating, 162 reviews

Guest favourite

Apartment in City of Orange

Elevated City Living•NEW 1BR•Gym• NYC Train 1block

Welcome to a brand-new modern 1-bedroom condo just 1 block from the NYC-bound train-reach Manhattan in 30 minutes. Ideal for couples, business travelers, & NYC visitors seeking comfort outside the city. •Walk to NYC train •Newark airport- 15min •Free indoor parking • Brand-new condo w. modern finishes •Gym, lounge (workspace-friendly) outdoor patio & grill •food/restaurants/markets nearby •Fully equipped kitchen, black out curtains •king pullout couch •Secure building- easy self check-in

ValueLocationHospitality

4.98 out of 5 average rating, 40 reviews

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.

Apartment in Montclair

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

LocationFamilyCleanliness

4.98 out of 5 average rating, 135 reviews

Top Guest favourite

A cozy sleeping area features a neatly made bed with light bedding and a textured throw. Above the bed, three decorative prints hang on the wall. A mirrored closet reflects the space, creating an open feel, while soft lighting enhances the peaceful ambiance.

Guesthouse in Montclair

The cozy studio apartment of Montclair

“Take care of this space—a beautiful, cozy underground studio that feels like a little retreat. It’s truly a gem. It’s not just warm and charming—it’s a kind of warmth that radiates style.” Relax and enjoy this underground Studio. Please read the house manual and house rules before booking for check restrictions. This space is intended for rest and sleep. It is suitable for a quick stay and fit the needs, but may not be ideal for guests seeking comfortable and pleasure stay. NO PARKING

ValueFamilyKitchen

4.87 out of 5 average rating, 128 reviews

Guest favourite

Home in West Orange

Modern Glam Getaway 30 minutes from NYC

Welcome to your luxurious home away from home! This modern, glamorous 5-bedroom, 3-bathroom house in West Orange, New Jersey, offers the perfect blend of comfort, style, and convenience. Be greeted by a bright, open layout designed for relaxation and connection. With sleek modern finishes, high-end furnishings, and thoughtful touches throughout, this home easily accommodates up to 10 guests — ideal for families, groups, or business travelers seeking both space and sophistication.

LocationFamilyHospitality

5.0 out of 5 average rating, 10 reviews

Guest favourite

Guest suite in West Orange

Lovely is What They Call Me! by Toseb Design

**MONTHLY STAYS WELCOME** This oversized PET-FRIENDLY studio on the ground floor/basment unit offers a clean, comfy space, a spa bathroom, kitchen, smart TV & ample closet space. It also comes with a HUGE backyard equipped with a hammock, bonfire & dining/lounging areas. Client services are available too (see your Welcome Book once booked). Free private parking spot, easy check-in, 30 mins to NYC; 7 mins to trendy hot spots. Early/late check-in/out: $70 each. Pet fee: $100/pet.

FamilyLocationAir conditioning

4.95 out of 5 average rating, 43 reviews

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

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.

FamilyLocationEV charging

4.94 out of 5 average rating, 216 reviews

Guest favourite

Apartment in City of Orange

Garden State Haven Unit 2

This beautifully furnished 5-bedroom, 3-bath apartment on the second and third floor of the home has 2 full kitchens that offer a comfortable stay in a prime Orange location. There are 2 parking spaces in the driveway for guests. Just minutes from Downtown Newark and less than an hour to NYC, you'll have easy access to top attractions, dining, shopping, health and transit hubs. Bring the whole family to this great place with lots of room for fun.

LocationFamilySleep quality

5.0 out of 5 average rating, 18 reviews

Superhost

Guest suite in Livingston

Cozzy Get Away Priv.Apt/St Barnabas Hosp/ NYC/EWR

Near to RED BULL stadium Harrison 15 min and METLIFE stadium, Secaucus 30min. Private Apt/ Suite- attached to the house with a Private Entrance, 1 bedroom 2 beds, queen and a twin( please let me know in advance to prepare the twin bed) Kitchen, 1 Bathroom, & Sitting area, Television and Wi-Fi, it includes Refrigerator, Stove w/Oven, Toaster, Microwave, Coffee Maker and much more amenities. The Apt is located in the 2nd FL of the House.

FamilyValueCleanliness

4.86 out of 5 average rating, 631 reviews

Guest favourite

A modern living area features a comfortable dark sofa next to a sleek coffee table. A large TV is mounted on a white entertainment unit, while natural light flows through windows covered with blinds. Two floor lamps provide additional lighting, and a patterned rug adds texture to the space.

Apartment in Livingston

Lovely 1 bedroom apartment

A recently renovated and beautifully furnished modern apartment on the second floor of a small apartment building conveniently located 20 minutes west of NYC and 20 minutes drive from Newark International Airport in a safe, nice and quiet residential area. Livingston is a picturesque suburb serving as a bedroom community for a variety of commuters.

FamilyLocationQuiet

5.0 out of 5 average rating, 32 reviews