Holiday rentals in Chatham

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Top-rated holiday rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A serene landscape features a large farmhouse set against a clear blue sky, with lush green grass surrounding a tranquil pond. Reflections of trees and the farmhouse are visible on the water's surface, complemented by a rustic barn in the background.
Home in Far Hills
4.99 out of 5 average rating, 98 reviews

Pickle Farm

Meticulously maintained private quiet gated enclave featuring a restored vintage 1800 historic farmhouse and pastoral land- 1 hour from NYC. Registered movie and film location, featured in movies, commercials, documentaries and photo shoots. Agent handles negotiations, Prices vary. Minutes to train, Hamilton Farm, Pingry , Gill & Willow schools. Willowwood Arboretum, Bamboo Brook, Natirar, Several well known golf courses surrounded by hundreds of acres of preserved open land and state park.

Guest favourite
A charming, two-story barn conversion features a blue exterior with yellow accents on the garage doors. A spacious deck overlooks the surrounding greenery. The property is enclosed by trees, providing a serene environment, while a well-maintained lawn enhances the inviting outdoor space.
Barn in West Orange
4.87 out of 5 average rating, 179 reviews

Quaint Converted Barn

Terrific space with loads of light and openness. Overlooking golf course, hayloft converted into king bed with twin bunks in office nook and 1.5 baths. It's the perfect place to get away from it all. Barn converted into residence. Comfy, quiet and serene. First level has living room, dining room and a half bath with a spiral to the hayloft which is open to below and divided by closets that create the office nook but permit light over them. The barn is open, only the bathrooms have doors.

Top guest favourite
Home in Montclair
4.98 out of 5 average rating, 784 reviews

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.

Superhost
Serviced apartment in Florham Park
4.85 out of 5 average rating, 68 reviews

Commuter's Dream | Resort Amenities

Long-term rentals only. 📍 AVE Florham Park provides optimal positioning near major employers including BASF, Summit Medical Group, and Novartis. Ten minutes to Morristown and Madison, NYC transit, and Short Hills Mall. Each 2 BDR features high-end appliance packages, dedicated workspaces, and walk-in storage. Nearly 65,000 sq ft of amenities including private work suites, executive conference facilities, and high-speed WiFi. Huge fitness center and resort-quality pool. On-site 24/7 team.

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, 113 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

Superhost
A cozy living room features a light-colored sectional sofa adorned with decorative pillows. A circular coffee table is positioned on a soft area rug. Natural light fills the space through the windows, highlighting the hardwood floors and the adjacent dining area with a modern light fixture.
Home in Millburn
4.9 out of 5 average rating, 40 reviews

Turnkey Luxury & Comfort in the heart of Millburn

Our Millburn Cottage has everything you need for a peaceful and comfortable stay. This fully renovated and furnished English colonial boasts 4 bedrooms, 2 full, 2 half baths, & plenty of indoor and outdoor space to enjoy everything Millburn Short Hills has to offer. Steps from downtown Millburn, and a quick walk to the Millburn train station with direct train to NYC. IMPORTANT: No smoking/vaping, no animals, no parties. There is an extra guest charge after 5 guest, max 7 incl kids.

Guest favourite
A well-kept two-story house is presented with a neatly manicured lawn and a pathway leading to the entrance. Large windows with dark shutters adorn the front, and a white garage door is visible on the right side. Decorative statues are placed near the entrance.
Flat in Union
4.98 out of 5 average rating, 57 reviews

3 Bed Apt in Quiet Neighborhood

Beautifully maintained 3 bedroom apartment in peaceful neighborhood. Located 7 miles away from Newark Airport. 15 miles away from Midtown Manhattan NYC with bus 114 walking distance away. Metlife Stadium is located 13 miles away. Close to many restaurants and NJ famous malls like Short Hills/Jersey Gardens. Close to major highways in NJ including the Parkway, Turnpike and RT 78. Free Parking available on the driveway quiet and safe street. Great place to relax after exploring!

Guest favourite
A light-colored sectional sofa is arranged in a cozy living area, accompanied by a round wooden coffee table. A patterned rug lies beneath, while a potted plant and decorative vase with flowers add a touch of greenery. A world map decorates one wall, enhancing the space's ambiance.
Flat in East Orange
4.91 out of 5 average rating, 119 reviews

The space Gemini 1

Gemini 1 is a cozy space located in a quiet and safe neighborhood. It’s a stylish and comfortable apartment designed to make you feel at home. Perfect for up to 4 guests, with a full kitchen, Wi-Fi, keypad entry, and free parking. Just 8 min walk to the train to 🗽 NYC and 2 min to Watsessing Park. Only 15–17 min drive to ✈️ Newark Airport, 🎢 American Dream Mall, 🏟️ MetLife Stadium, ⚽ Red Bull Arena, and 🏒 Prudential Center. 30–35 min to 🏙️ Times Square

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
4.93 out of 5 average rating, 180 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 favourite
The bedroom features a spacious bed dressed in soft linens with accent pillows. Two bedside lamps provide warm lighting beside the bed. A piece of wall art is displayed above the bed, and natural light fills the room through a large window with sheer privacy shades.
Flat in Westfield
4.88 out of 5 average rating, 56 reviews

Steps to Downtown! Private,Spacious Unit! -3

Located just steps from downtown Westfield, and even closer to the train to NYC, this quiet neighborhood and clean 2bed/2bath unit is your perfect alternative to a hotel! NO contact entry, secure building with common area, gym, grilling area, and rooftop sitting area - this unit is waiting for you! Full kitchen, spacious living room, two full baths, and an in-unit laundry room make traveling a snap!

Guest favourite
The exterior of the unit showcases a blend of white and gray siding with large windows framing the entrance. A black door is set between stone accents at the base. Flower pots filled with various plants are arranged along the pathway, enhancing the welcoming appearance.
Guest house in Morristown
4.94 out of 5 average rating, 124 reviews

C&J Signature Stays Historic Renovated Apartment

Stay in your private, beautiful, bright two-bedroom unit with historical 1870s architectural details, including original brick walls, arched living room doorways, and stone kitchen walls. The unit was recently renovated to maintain its old charm while updating and modernizing the kitchen, living room, and two bedrooms. It is an excellent space for vacation or work. Fast Wi-Fi + Roku TV.

Top guest favourite
A well-lit, open layout is displayed, featuring a modern kitchen with stainless steel appliances and sleek cabinetry. Four yellow bar stools are positioned at a kitchen island. A black sectional sofa sits in the living area, with natural light streaming through large windows.
Flat in Livingston
5 out of 5 average rating, 23 reviews

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.

Popular amenities for Chatham holiday rentals

  1. Airbnb
  2. United States
  3. New Jersey
  4. Morris County
  5. Chatham