Holiday houses in Caldwell

Chic Family & Pet Friendly Apt by Toseb Design

*MONTHLY STAYS & PETS WELCOMED* 10% OFF Non-refundable stays. Spend time with the family at this peaceful 2BR apt. This peaceful 2nd fl unit is equipped with a designated workspace, fully stocked kitchen & more. Enjoy the hammock, the bonfire or dining/lounge areas in the HUGE yard. Client services are available upon request once booked. Comes with private parking & easy check-in. Just 30 mins to NYC; 5 mins to trendy hot spots. Early/late check-in/out is available for $70/ea. Pet fee $100/pet.

*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.

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.

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.

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.

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!

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.

Pvt. studio close to the city

This private, family-friendly suite features a spacious living room that opens to a secluded patio with a fire pit and outdoor dining area—an ideal retreat for a small family or a couple seeking peace and quiet while staying close to the city. Inside, you'll find a cozy living space with a queen bed, an attached bathroom, a sofa bed, a TV, a writing desk, and a convenient kitchenette equipped with a fridge, microwave, and coffee maker.

Chic & Central-Near Transit, Close to Everything

Welcome to this spacious and well-lit studio located on the 2nd floor of a quiet multi-family home. Just minutes from the train station, you’ll enjoy a quick and easy commute to Manhattan. The studio offers a comfortable layout with ample space to relax, work, or unwind. Perfect for solo travelers or couples looking for convenience, comfort, and location all in one

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.

Montclair Cozy Nook

What a lovely place. Come and enjoy our stylish cozy nook. Enjoy the comforts of peace and quiet, take a stroll through upper Montclair enjoying multiple delicious foods from various restaurants and in the end, tasty desserts from various ice cream shops. Small cozy place for your own personal comfort!

Spacey private studio located on dead end street.

Large comfy basement living room and bedroom studio with separate garage entrance. Your space is totally independant. Its not shared with anyone. Located on a dead end street, safe and very quiet. Parking available on request. I will be on site to assist with any needs.