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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Guest favourite
A cozy studio apartment features a queen bed with a floral duvet and soft pillows. A television is positioned on a wall, while a closet area provides hangers and storage. Natural light filters through blackout curtains, enhancing the tranquil atmosphere.
Flat in City of Orange
4.94 out of 5 average rating, 108 reviews

Luxury Reno w/ Private Entry

Unique studio apartment completely renovated with private entry and self check in from electronic lock. Queen bed w/ Sealy pillowtop mattress and blackout curtains for the best sleep. Free laundry detergent! In unit laundry. Access to the backyard and BBQ grill. 420 friendly in backyard only. Central to highways, shopping, and restaurants. Easy 40 min commute to NYC via Orange NJ Transit station 7 mins walking. Minutes from Newark Airport, Prudential Center, American Dream & Metlife Stadium

Guest favourite
A modern living area features a comfortable sofa adorned with decorative pillows, an enclosed television unit, and a stylish desk with a chair. Natural light is provided by windows with blinds, highlighting the sleek grey flooring and contemporary decor.
Flat in Livingston
4.9 out of 5 average rating, 77 reviews

Home away from Home in Livingston NJ

Beautiful, private, modern and recently renovated 1 bedroom apartment 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. Getting around from Livingston is easy with close proximity to I-280, I-80, the Garden State Parkway, New Jersey Turnpike and Rt 24 as well as public transit stations in neighboring towns.

Guest favourite
A spacious bedroom is highlighted with a comfortable bed adorned with soft linens. A modern workspace, featuring a sit-stand desk and ergonomic chair, is present. The inviting living room includes a large smart TV and cozy furniture. The bright kitchen showcases sleek cabinets and a quartz island, while the private balcony features a stylish egg chair.
Flat in Montclair
5 out of 5 average rating, 5 reviews

Montclair 2BD/2BA Pets Parking Laundry Train!

INQUIRIES ONLY to ensure we're a right fit, NO REQUESTS please. Calling all families in need of temporary housing! Whether you're relocating for a job, undergoing renovations, or curious to experience the 4th best town in New Jersey... end your search with this 1000 sq ft pet-friendly, 2 bedroom 2 bath with in-unit laundry, ergonomic workspace, king bed, high-speed Wi-Fi, off-street parking, and private balcony. Still not convinced? Read further or reach out to discover how we can serve you.

Top guest favourite
A tranquil garden scene features a stone fountain surrounded by lush greenery and a variety of colorful flowers. The arrangement includes pink geraniums, purple blooms, and vibrant foliage, creating a peaceful outdoor space with a mix of textures and colors.
Loft in West Orange
4.99 out of 5 average rating, 278 reviews

*Fragrance Free-Cozy Clean Safe-Easy Commute NYC!

**The studio is private, 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 early or late as you like) ***BEFORE REQUESTING TO BOOK*** please read my entire listing *As you can see by my photos, ratings and reviews this really is a lovely place to stay, I am an attentive host, but please indulge me and read on.... * I keep a fragrance free house and require that guests be fragrance free.

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
4.87 out of 5 average rating, 126 reviews

Unique Carriage House-on historic estate-near NYC

Experience an enchanting 3-bedroom carriage house approximately 20 miles from NYC. The house offers a unique blend of vintage rustic charm and modern comfort on a historic private estate, a one of a kind American gem. Conde Nast Traveler (2025) hailed it one of the "Best Airbnbs in New Jersey." Ideal for any occasion: “Fam Travel”, wedding base, corporate travelers, relocation, remodeling, traveling doctors,nurses, tourists sightseeing in NYC or events at MetLife "FIFA World Cup", plus.

Top guest favourite
Flat in Montclair
5 out of 5 average rating, 53 reviews

Sunny and cozy apt near Montclair downtown and NYC

Happy Halloween 🎃 Newly renovated, sunny and cozy apartment in the heart of Montclair. Your hostess, Sandra lives upstairs. Perfect for solo travelers or couples, this pet friendly space features two bedrooms, a bathroom, a fully equipped kitchen, a spacious living room, a brand new washer and dryer, a beautiful wooden deck and a gated/fenced backyard with free parking. Conveniently located near Walnut Street train station to NYC and near downtown Montclair for restaurants and shops.

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
4.97 out of 5 average rating, 91 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
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.
Guest house in Montclair
4.8 out of 5 average rating, 65 reviews

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.

Guest favourite
The living room features a comfortable sectional sofa with a throw blanket draped over one end. A glass coffee table sits in the center, surrounded by soft carpeting. Two lamps provide gentle light, and large windows allow natural light to fill the space. A map-themed artwork decorates one wall.
Flat in Caldwell
5 out of 5 average rating, 118 reviews

Bright and Airy 6- Room Apartment

Spacious and bright, 2 separate bedroom 2nd floor apartment in Caldwell, NJ in a quiet and safe neighborhood with off-street parking for 1 car. Close to NYC transportation, restaurants and shopping. This is perfect for business travelers in need of a short term rental, such as, traveling nurses, those relocating to the area or who are in between homes due to construction, etc., as well as, those who want to go into NYC for a show but don't want to pay NYC hotel prices.

Guest favourite
A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator and oven. Counter space is utilized for meal preparation, with a coffee maker and utensils visible. Natural light floods the room through a nearby window, illuminating the stylish tile flooring.
Home in Montclair
5 out of 5 average rating, 8 reviews

Cozy Home on Dead End St – Steps from the Park

Discover the perfect blend of comfort and tranquility in this charming 1BR/1BA retreat, nestled on a quiet dead-end street next to a beautiful park. Ideal for nature lovers and those seeking relaxation, yet just minutes from dining, shopping, and attractions. Enjoy a fully equipped kitchen, cozy furnishings, outdoor patio with a bbq, and a peaceful atmosphere. This charming space offers privacy, convenience, and tranquility. Book now and experience the perfect getaway!

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.
Guest house in Montclair
4.94 out of 5 average rating, 33 reviews

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.

Superhost
A spacious bedroom features a queen bed with coral-patterned bedding and a decorative pillow. Nightstands with lamps are positioned on either side. A simple seating area with a love seat is visible, and bookshelves are located above the bed, providing additional storage.
Guest suite in Livingston
4.86 out of 5 average rating, 598 reviews

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

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.

Popular amenities for Caldwell holiday rentals

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