Vacation rentals in Caldwell

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.)

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.

Carriage House on historic estate "Best Airbnb NJ"

Relax in a 3-bedroom private carriage house on a historic estate appx 20 miles from New York City. This one-of-a-kind retreat blends vintage rustic charm with modern comfort, offers privacy, space, and a timeless vibe rarely found near NYC. Recognized by Condé Nast Traveler (2025) as one of the “Best Airbnbs in New Jersey,” ideal for families, corporate travelers, traveling medical and tourists attending NYC events, FIFA World Cup—plus walk to it all shops, restaurants, plus. +Free Parking

Private & Spacious 2 Bed Apt - Prime Montclair

⭐️Perfect Upper Montclair location! ⭐️Spacious 2-bed apartment on 1st floor of Victorian house. ⭐️Private entrance. ⭐️Off-street parking for 1-2 cars. ⭐️Fully stocked kitchen with gas stove, dishwasher, microwave, coffee maker fridge-freezer. ⭐️Comfortable king-size beds. ⭐️Strong WiFi and TV with Netflix. ⭐️In unit washer and dryer. ⭐️Close to trains and bus to NYC, parks, grocery stores, cafes, restaurants, American Dream Mall, MetLife stadium. ⭐️Super friendly hosts who live on-sit

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

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!

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.

* Fragrance Free - Quiet, Safe Area - NYC 30 min

*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 often, early, late) ***BEFORE REQUESTING TO BOOK*** please read the following rules and info. In your message, when you request to book, please confirm that you have read the rules and agree to honor them. I keep a fragrance free home and require that guests be fragrance free too.

Your Happy place Away from Home

Kick back and relax in this just renovated, calm and stylish apartment on the second floor of a small apartment building. Conveniently located 35 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.

Montclair Nest

Cozy 1 bedroom apartment. Third floor walk-up with full kitchen and private bathroom. Three blocks from trains and buses to New York City, Hoboken and Newark. Ten minute walk to downtown Montclair with restaurants, shopping, library, theater and more.

Private Short Hills Retreat

Private entry guest apartment in beautiful Short Hills, NJ. 45 minutes by train to NYC (10 minute walk to train), approximately 30 minutes by car. Updated and comfortable 1 bedroom, 1.5 bath, living room, kitchen, washer & dryer.

Cozy Studio Apartment

Live comfortably in this cozy studio apartment . This home is Central to so many cool areas. Less than a mile from Downtown Montclair and only a short walk to the Glen Ridge Train station for a 30 min train ride into NYC.