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Holiday houses in Westwood

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Top-rated holiday rentals in Westwood

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!

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, 132 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.

Superhost
The exterior of the house is set among lush greenery and features a large elevated deck that wraps around the structure. Large windows provide natural light, and the building is supported by a prominent boulder, blending harmoniously with the surrounding forest.
Home in Ossining
4.84 out of 5 average rating, 168 reviews

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.

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, 171 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!

Guest favourite
A rustic lakeside cabin is nestled among trees at dusk, featuring stone and wood exteriors. Warm light spills from windows, inviting exploration. A stone pathway leads to the entrance, framed by planted greenery and earth-toned landscaping, contributing to the serene atmosphere of the property.
Home in Airmont
4.97 out of 5 average rating, 79 reviews

Aspen In Airmont

Welcome to "Aspen in Airmont", a unique lakeside cabin experience in Airmont, NY. Offering 9 beds across 4 rooms, including a lavish Master Suite with Tempurpedic mattresses, a Jacuzzi and separate shower. Our home is Highlighted by a 16-seat dining area, cozy indoor fireplace, and outdoor fire pit. Fits Small/Large Groups. Enjoy the year-round hot tub and in-ground trampoline. The perfect getaway with Friends/Family for vacation or Shabbos. (Located within an Eiruv, close to a local Shul)

Top Guest favourite
A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.
Cabin in Greenwood Lake
4.96 out of 5 average rating, 491 reviews

Cabinessence -on Greenwood Lake, NY #34370

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

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, 390 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

Guest favourite
Guest suite in Westwood
4.7 out of 5 average rating, 20 reviews

XL Private Suite | NYC in 55 min | King Bed | WiFi

Enjoy your stay at our XL, bright one-bedroom guest suite with separate entrance! *Close to NYC! 5 minute walk to Hillsdale NJ Transit station, which gets you to Penn Station within 1 hour. *Supermarket, cafes within walking distance (5 minutes). *Own parking. *Fully private suite with washer and dryer, king sized bed, Wi Fi, 2 AC Units, 3 walk in closets. *I live in the same house (separate entry) & happy to help with anything. *Unique location - dead end street, with parks nearby.

Guest favourite
A spacious bedroom features a queen-size bed with a light-colored blanket, complemented by soft, pink pillows. The room is illuminated by natural light from two windows, and cozy seating is arranged nearby. Additional storage is available in built-in closets.
Apartment in Fair Lawn
4.88 out of 5 average rating, 442 reviews

Fair Lawn 1bedrm apt, wi-fi, TV, kitch, parking, ent

Fully furnished 1 bedroom apt. with Qn size bed, European kitchen, bath, private parking, entrance, bedroom/living room, dining. Queen size Aerobed for additional guests. Fastest 5G/400MBps Wi-Fi, cable TV, + Netflix, Showtime. The kitchen/dining room has Tyent ACE-11 water system, refrigerator (water and ice), microwave, large countertop toaster oven, coffee maker, dishwasher, and other appliances. Great for couples, solo adventurers, business travelers, or small families.

Top Guest favourite
Castle in Greenwood Lake
5 out of 5 average rating, 10 reviews

Iconic Greenwood Lake Castle

Built in 1915 during the Golden Age of Greenwood Lake by Rudolph Gudewill, Greenwood Lake's only castle and guest house is filled with local lore and a legendary past. From the Gudewills it was sold to the Tiedemanns, but the property's fame came when NY Yankee Derek Jeter purchased the castle compound in 2003. The torch has passed once again and now for the first time in history the lakefront castle guest house is available for short term rental. STR Permit # P25-0524

Guest favourite
A tree-lined street is depicted, leading towards the Hudson River, visible in the distance. Residential buildings line both sides, with vehicles parked along the curb. Greenery enhances the scene, contributing to a serene atmosphere, while the rolling hills rise beyond the river.
Apartment in Hastings-on-Hudson
4.85 out of 5 average rating, 353 reviews

Entire 2 Bedroom apt, Hastings-On-Hudson near NYC

This brand new two-bedroom apartment is perfect for experiencing the beauty of the Hudson Valley while being a 5-10 min walk away from the Metro North station (45 min ride to Grand Central). It is very close to the heart of downtown that is filled with locally well-known restaurants, coffee shops, and a farmers market. This apartment includes a spacious backyard, perfect to enjoy breakfast with your family or group of friends with a view of the Hudson River.

Guest favourite
Home in Hackensack
5 out of 5 average rating, 5 reviews

Modern 5BR 3 Full Bath, Fits 10 guests near NYC

Welcome to your home away from home! This newly furnished retreat features a brand-new kitchen, beautifully renovated bathrooms, modern furnishings, and bright, inviting spaces throughout. Enjoy the huge outdoor patio and fully equipped outdoor kitchen, perfect for relaxing or entertaining. Conveniently located near New York City and just 20 minutes from MetLife Stadium, it’s the perfect getaway for families, friends, and travelers seeking comfort and style.

Popular amenities for Westwood holiday rentals