Holiday houses in Eastchester

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Top-rated holiday rentals in Eastchester

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

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Guest favourite

A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.

Home in Rye

4.91 out of 5 average rating, 144 reviews

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

ValueFamilyHospitality

Top Guest favourite

A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.

Cottage in Warwick

4.99 out of 5 average rating, 133 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

FamilyLocationComfort

Guest favourite

A comfortable bed is positioned against a soft gray wall, with crisp white linens and two pillows arranged neatly. Each side is complemented by a small nightstand with a lamp, providing gentle illumination in the room.

Apartment in New Rochelle

4.92 out of 5 average rating, 65 reviews

The Uptown Comfort Suite

Relax with the whole family or just you at this peaceful place to stay. Enjoy comfort services. Comfortable bed and soft sheets, long mirror to complete that dress mode for all occasions. We have a powered office desk for the need to stand or sit. All around great TV services with movie channels plus more. A large kitchen that seats four. This place is an extreme comfort to you’re delight for all ages and occasions. Also enjoy convenient free parking on the premises. Recording studio ☎️✅pricing

FamilyLocationComfort

Guest favourite

A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.

Home in White Plains

4.91 out of 5 average rating, 173 reviews

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

LocationFamilyBathroom

Top Guest favourite

A cozy living room features a large flat-screen TV mounted on the wall, accompanied by a sleek entertainment unit. A comfortable couch is draped with a soft blanket, and an armchair is positioned nearby. Natural light enters through two windows, brightening the neutral decor.

Guesthouse in Mamaroneck

4.97 out of 5 average rating, 115 reviews

Spacious guest suite near water

Welcome to your perfect home away from home! Enjoy a spacious and newly renovated basement suite with windows and separate entrance in a private house, perfect for up to four guests. Ideal for couples, small families, or business travelers. This cozy retreat, combines privacy and comfort in a quiet neighborhood. Whether you’re here for a short trip or an extended stay, this apartment offers everything you need for a comfortable and relaxing experience. Book now and start planning your visit.

FamilyValueQuiet

Guest favourite

An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.

Cottage in Greenwood Lake

4.97 out of 5 average rating, 391 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

LocationValueWalkability

Superhost

The bedroom features a spacious bed with light-colored bedding against a backdrop of warm red and green walls. Natural light filters through multiple windows, adding brightness to the cozy space. A dark wood dresser complements the decor.

Apartment in Eastchester

4.72 out of 5 average rating, 183 reviews

One Bedroom w/ Great Location

Centrally-located spacious one bedroom apartment, clean and cozy. Private entrance to the unit. Walking distance to grocery stores, trending restaurants, pharmacies, CVS, cleaner's, gym, salons and massage. Very safe neighborhood with walking distance to several parks. Public transportation to Grand Central in New York City within 30 minutes on express train and 50 minutes on local train. The apartment is a 4 minute drive to Metro North Railroad Station and the Scarsdale Village.

LocationValuePets

Top Guest favourite

A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.

Apartment in Ossining

4.96 out of 5 average rating, 552 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $19 cleaning with or without pets.

FamilyValueLong stay

Guest favourite

Home in Greenwich

4.93 out of 5 average rating, 71 reviews

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage blends rustic charm with modern luxury. Cozy up by the stone fireplace, cook in the chef's kitchen, or unwind on the river-facing deck. Splash in the heated pool, soak in the year-round hot tub, gather by the gazebo, or spot wildlife along the water. Two fire pits, river views, and pure tranquility — just 5 min to downtown Greenwich and 35 min to NYC. Your riverside escape awaits.

ValueLocationPets

Top Guest favourite

The cottage is tucked amidst vibrant autumn foliage, framed by trees. A large front deck, furnished with two chairs, provides a serene entry, while the three expansive windows invite natural light. The wooden exterior blends harmoniously with the surrounding woodland.

Guesthouse in Bedford Hills

5 out of 5 average rating, 93 reviews

The Perch: Saltwater Pool Woodland Cottage Retreat

*Pool closes for the season on Sept 15 and reopens May 2027* inquire for details The Perch, a design-forward woodland cottage surrounded by nature just one hour from NYC perfect for couples escaping the city for a quiet Hudson Valley weekend. Spend slow mornings overlooking the woods, afternoons by the saltwater pool, and evenings exploring Bedford’s historic village restaurants and trails. "The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa

FamilyLocationView

Top Guest favourite

A detached studio with a charming exterior is surrounded by lush greenery and landscaped gardens. The structure features large windows framed in dark trim, allowing natural light to fill the interior. A stone pathway leads up to the entrance, enhancing the inviting appearance of the property.

Guesthouse in Larchmont

4.99 out of 5 average rating, 72 reviews

Beautiful guesthouse - Larchmont

Newly furnished 2nd floor detached studio with private entrance. One large bedroom with queen-size bed, full bath with spacious shower, kitchenette, and armoire. Lots of light and beautiful views overlooking luscious landscaping and the surrounding quiet Rouken Glen neighborhood. Studio sits over garage. Access to spare washer/dryer in our basement is also available. 4 min drive to Larchmont station (35 min train to Grand Central).

LocationValueWalkability

Superhost

Home in New Rochelle

4.9 out of 5 average rating, 91 reviews

Near NYC ~ Fire pit, Backyard & Parking

Comfortable New Rochelle retreat just minutes from NYC and the train. Fully stocked kitchen, coffee bar, elegant bathroom w/ rainfall shower, cozy fireplace, Spacious backyard w/ seating, fire pit & BBQ 🚆 6 mins to the train, 35 mins to NYC ✈️ Convenient access to airports (JFK, LGA, Newark, Westchester), Long Island, White Plains, Davenport wedding venues, trails & parks Ideal for work or vacation year-round. Book now!

LocationValueAir conditioning