Vacation rentals in Caldwell

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Top-rated vacation rentals in Caldwell

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Superhost

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, 124 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 excursion American Dream, Prudential Center, plus

Guest favorite

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.

Apartment in City of Orange

4.93 out of 5 average rating, 103 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

Top guest favorite

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

4.97 out of 5 average rating, 117 reviews

Fragrance Free-Beautiful Cozy Home Away From Home

**BEFORE REQUESTING TO BOOK, please read my entire listing for important info and policies** As you can see by my ratings, photos and reviews this truly is a lovely place to stay and I am an attentive host, but please first indulge me and read on... *Exceptions to the rules are made depending on the request. *I maintain a fragrance free home and require that guests be fragrance free as well. Please no perfume, cologne, essential oils. More Details Below *Located in a very safe neighborhood.

Top guest favorite

A bright living area is depicted with a white sofa adorned with a red accent pillow. A simple coffee table sits in front, complemented by a decorative plant. Natural light filters through sheer curtains, casting gentle shadows across the soft rug beneath.

Apartment in Montclair

5 out of 5 average rating, 46 reviews

Sunny and cozy apt near Montclair downtown and NYC

Welcome to our home! 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 favorite

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

4.97 out of 5 average rating, 86 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 favorite

A modern living area is presented with a sleek gray sofa and a minimalist coffee table. Natural light fills the space through adjacent windows. A round mirror is mounted on the wall, complementing the contemporary decor, which includes framed artworks and a comfortable accent chair.

Apartment in Montclair

4.94 out of 5 average rating, 65 reviews

Renovated & Spacious 2 BR Entire Apt in Montclair!

A newly renovated & decorated 2 bedroom + office apartment in downtown Montclair! This apartment has tons of natural sunlight and is on a third floor walk-up. Close to amazing restaurants, coffee shops, boutiques, markets, parks, bus/train to NYC etc. Transportation to NYC is less than an hour. 0.5 Miles away from the train station! This space is great for families, working professionals & friend groups. Parking on-street & off-street available.- Very close to Metlife Stadium as well!

Top guest favorite

A well-lit living space features a comfortable sofa and a red sectional, with decorative cushions adding color. A wooden coffee table with a rustic design sits at the center. Natural light enters through two windows framed by flowing curtains, and a ceiling fan provides airflow.

Apartment in Montclair

4.94 out of 5 average rating, 54 reviews

Charming Apt Walkable to Shop, Eat & NYC Transport

-Spacious 3rd Floor Apt in Renovated Victorian Home -Prime Location to NYC-Midtown in 30 minutes. Walk to train/bus. -Walk to Montclair's restaurants/shopping areas. -King Size Bed -TV & WiFi -All linens are sanitized extensively to ensure you an extremely clean experience--you can flop on any bed and be assured that no one else did the same. -You find the place the way I would like to find a place so I want to treat you the way I would like to be treated with kindness & care.

Guest favorite

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

4.75 out of 5 average rating, 51 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 favorite

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.

Apartment in Caldwell

5 out of 5 average rating, 117 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.

Superhost

A spacious loft bedroom features a king-size bed with neutral linens. A mirrored wardrobe reflects light and enhances the sense of openness. A small fridge and microwave are positioned next to a cozy seating area, complemented by warm wooden flooring and natural light from the window.

Home in Montclair

4.8 out of 5 average rating, 30 reviews

Beautiful cozy loft

Forget your worries in this spacious and serene space. This 3rd Floor Loft is Located in an entertainment area with many great restaurants! Situated between two parks as well as two train stations going to NYC. This loft has a small fridge, microwave, and Keurig machine. A quiet, safe place has a style all its own. Close Newark and JFK airports. Prudential Center 4.9 miles MetLife Stadium 7.8 miles American Dream 8 miles Smoking is allowed outside of the property.

Top guest favorite

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, 120 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 favorite

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

4.93 out of 5 average rating, 27 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.