Vacation rentals in Port Chester

5 out of 5 average rating, 8 reviews

The exterior view showcases a bright, newly constructed home with white siding and a stone accent at the lower level. A spacious porch with seating is visible, along with a well-maintained lawn and a fenced yard, creating a welcoming entrance.

Home in Fairfield

Newly built twin beach house within steps to beach

Keep it simple at this peaceful and centrally-located home. Newly built in 2019! Premier beach living at its finest. Steps to Fairfield’s beaches and less than a mile to downtown restaurants, shops, and bars. Fenced backyard. Central air throughout. Decks off the front and back with a Weber grill. Furnished with luxury furniture, sheets, comforters, and pillows. Smart TVs in every bedroom and living room. Tesla charging station at the house. Identical home next door available for larger bookings

4.85 out of 5 average rating, 143 reviews

A vibrant mural of a natural landscape adorns the walls, featuring mountains, waterfalls, and lush greenery. The bathroom includes a black toilet, a wood vanity with a sink, and a large framed mirror. A colorful rug is positioned on the tile floor.

Home in Ossining

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

4.99 out of 5 average rating, 190 reviews

A charming studio cottage is nestled among trees, with a covered porch adorned by an American flag. Steps lead up to the entrance, and a wooden railing provides safety. Seasonal foliage in warm colors surrounds the area, complementing the rustic setting.

Cottage in Cortlandt

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

4.93 out of 5 average rating, 30 reviews

A woven basket contains a bottle of moisture loving lotion, a green applicator, and two black towels. One towel is labeled 'Makeup,' suggesting its purpose for beauty routines.

Home in Monroe

Rustic Blues Cottage Retreat

Kick back and relax in this calm, stylish space with an escape to the picturesque Hudson Valley for a Retreat like no other! Immerse yourself in the vibrant colors of the season, surrounded by the region's most breathtaking foliage. Our curated getaway combines adventure, relaxation, and festive fun. *PULL OUT COUCH in living room* Nearby: Woodbury Commons Premium Outlets Flagship Cinemas Legoland Renaissance Faire Pure Terror Scream Park Warwick Wineries Pumpkin Picking Apple Picking Hiking

4.94 out of 5 average rating, 114 reviews

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

5 out of 5 average rating, 102 reviews

A cozy cabin nestled among trees is shown at dusk, with warm light streaming from the windows. An outdoor fire pit is visible, adding an inviting glow to the natural surroundings. Tall trees frame the scene, enhancing the tranquil atmosphere.

Cottage in South Salem

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

4.97 out of 5 average rating, 59 reviews

A lakeside retreat is nestled among lush greenery, featuring a spacious deck with blue seating. A gentle slope leads to the water's edge, where a small area is provided for relaxing. A large tree casts shade over the grassy yard, enhancing the natural setting.

Home in Putnam Valley

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

4.87 out of 5 average rating, 150 reviews

A bright bedroom features two spacious beds covered with white linens and soft blankets. Large windows and skylights fill the room with natural light, showcasing views of greenery outside. Blue curtains frame the windows, and a wicker basket with towels is positioned on a side table.

Home in Monroe

Sunlit & Peaceful. Hot Tub. Monroe. 1hr fr NYC.

Welcome to our cozy retreat in Monroe, NY where relaxation awaits you. Our charming Home is bathed in natural sunlight, thanks to numerous windows and skylights, creating a warm and inviting ambiance. Nature lovers can explore the scenic Heritage Trail, perfect for leisurely walks or bike rides. If shopping is on your agenda, the Premium Outlets at Woodbury Commons are just a short drive away. For family fun, Legoland is a nearby attraction, promising excitement, and joy for all ages.

4.88 out of 5 average rating, 26 reviews

An open living area features a spacious sectional sofa with contrasting pillows, a wooden coffee table, and a plush area rug. Arched windows and a high ceiling create a bright atmosphere, complemented by decorative wrought iron railings and a cozy fireplace.

Villa in Monroe

Mediterranean Villa

Whether you’re looking for a relaxing getaway or a family trip filled with adventure, you’ll love staying at the ‘Mediterranean Villa’ in the scenic Hudson Valley. Tucked away in Monroe, NY this Villa offers 5-bedrooms, 4-bathrooms, a wood-burning fireplace & enough space for your family to come together and make new memories. Location provides easy access to local attractions: take a day trip to the Catskills, shop locally at the Woodbury Commons or check out the local wineries.

4.94 out of 5 average rating, 128 reviews

A serene gathering area is nestled among lush greenery, featuring four dark wood chairs arranged around a small fire pit. A gentle stream flows nearby, surrounded by diverse trees and foliage, creating a peaceful atmosphere for relaxation in nature.

Apartment in Suffern

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

4.82 out of 5 average rating, 11 reviews

A bright kitchen area is featured with modern appliances, including a refrigerator and oven. A spacious island with high white stools invites casual dining. Natural light floods the open space, showcasing hardwood floors that complement the cozy living area in the background.

Home in Bridgeport

Modern + Spacious 5BR/2BA Home, Renovated Backyard

✨ Modern Renovated 5BR/2BA Home in Ideal Location ✨ Stay in style and comfort at this newly renovated 5-bedroom, 2-bathroom home, just steps from the best dining, shopping, and attractions. 💡 Why You’ll Love It: • Fully Equipped Kitchen 🍳 – Cook like a chef! • Luxury Bedding 🛏️ – Rest easy with premium linens. • Spacious Living Areas 🛋️ – Perfect spaces to unwind. • Stunning Backyard 🌳 – Relax and entertain in style. Book now for an unforgettable stay!

4.97 out of 5 average rating, 78 reviews

Home in Putnam Valley

Crystal Wave LakeHouse

Make some memories at this renovated, family-friendly Lakefront Oasis! Kayak, Swim, Boat & Fish on your own Peninsula with Lake Frontage on 3 Sides of the Property! Views of the Lake from Almost Every Window! Included is an extra 600 sq ft cottage that has been completely renovated for your enjoyment with a pool table. Utilized as a gaming room & yoga studio! There is a pullout sofa as well for extra guests with a bathroom a few steps away in the main house!

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Stay near Port Chester's top sights

The Capitol Theatre22 locals recommend

AMC Port Chester 1411 locals recommend

Little Thai Kitchen7 locals recommend

Costco Wholesale6 locals recommend

PepsiCo6 locals recommend

Citarella Gourmet Market - Greenwich, CT5 locals recommend

Other great vacation rentals in Port Chester

4.83 out of 5 average rating, 48 reviews

A calm river views the serene water under a clear blue sky, with gentle waves lapping against the rocky shoreline. Rolling hills frame the background, providing a natural landscape that blends with the horizon.

Apartment in Cortlandt

Peaceful Hideaway

4.91 out of 5 average rating, 74 reviews

The top floor of a two-story house is visible, featuring a spacious covered porch adorned with potted plants and outdoor furniture. Sunlight filters through surrounding trees, highlighting the structural details and serene outdoor setting.

Apartment in Peekskill

The Peekskill Treehouse

4.84 out of 5 average rating, 25 reviews

A modern kitchen is equipped with stainless steel appliances, including a large refrigerator and a gas stove. White cabinetry and countertops made of light-colored stone create a clean and bright space. Ample recessed lighting illuminates the room, and a window offers natural light.

Apartment in Newark

15% OFF | NYC | EWR | The Modern Mingle

5 out of 5 average rating, 24 reviews

A large outdoor pool is surrounded by a stone patio, equipped with several lounge chairs. Lush greenery lines the perimeter, providing a natural backdrop. Soft sunlight reflects off the water, enhancing the inviting atmosphere of the spacious area.

Home in Dix Hills

Nice getaway with your family.

4.96 out of 5 average rating, 24 reviews

Home in Yonkers

Sweet & cozy house

5 out of 5 average rating, 26 reviews

The exterior of the house is surrounded by trees, featuring large windows that invite natural light. A stone patio includes outdoor seating and a grill, with an umbrella providing shade. The property is enveloped by greenery, offering a serene atmosphere.

Home in Philipstown

Charming Retreat 3B/3B Garrison, 2 Fireplaces

4.86 out of 5 average rating, 7 reviews

A sandy beach stretches along the shoreline, bordered by calm waters. Two individuals are seated on a blanket near the water's edge, with scattered boats visible in the distance. The sky is overcast, with clouds creating a serene atmosphere.

Home in Glen Head

Cozy 4BR+3BA for entire family/bay of GlenHead NY