Holiday houses in Rye

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Top-rated holiday rentals in Rye

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

Guest favourite

Apartment in Greenwood Lake

4.94 out of 5 average rating, 79 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

Superhost

Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 182 reviews

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

Guest favourite

Home in Monroe

4.96 out of 5 average rating, 23 reviews

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

Guest favourite

Home in Greenwood Lake

4.96 out of 5 average rating, 53 reviews

Water's Edge Lakefront Home

As much as we will miss all the charm and beauty of summer at Greenwood Lake, fall is an incredible time to be surrounded by these colorful mountains. Come check out this beautiful season in the Hudson Valley and see all the area has to offer for a wonderful weekend or longer getaway. Activities include orchids for apple and pumpkin picking, cider donuts, farm markets, breathtaking, fall foliage, Renaissance Fair, hiking, breweries, wineries, golf courses, etc Come enjoy! STR Permit # 21 7853

Guest favourite

Home in Levittown

4.83 out of 5 average rating, 24 reviews

Romance Vacation Sweet Home

Brand New Renovation by the Arquitech John Stumpf from Long Island ,that took my design to an amazing level of luxury tranquility and the most trendy space That you can only dream off. Have 3 bedrooms and 2 bathrooms Exquisite kitchen, stunning first floor and second floor, loft work area for people that need to work remotely and amazing large backyard for whoever wants to feel the fresh air the warmth of beautiful fireplace with nice hot cocoa or great glass of wine Free parking,Grill ,

Guest favourite

Home in Greenwood lake

4.95 out of 5 average rating, 38 reviews

Secluded Cottage on the Lake with Hot Tub

Enjoy the fresh air and surrounding nature over Greenwood Lake in our 2-bedroom cottage located on the 28-acre private property of Timber Hill Estates. This property is secluded and peaceful. Enjoy the brand new hot tub overlooking the lake. There is indoor gas fireplace, outdoor grill and an outdoor fireplace. In the summer, this unique property also includes lake access and a private boat launch and slip. This amenity is an additional charge and is available upon request May-September.

Guest favourite

Home in Northport

4.94 out of 5 average rating, 114 reviews

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.

Guest favourite

Home in Ocean Beach

5 out of 5 average rating, 43 reviews

Sunny Spacious Pet Friendly Steps from the Beach

This ideally located four-bedroom home is the perfect spot for your family's vacation. The home features a spacious deck, central air conditioning, WiFi, 4 Smart TV's, a Sonos sound system and YouTube TV. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. There are 2 full bathrooms as well as an outdoor shower. Fully equipped including beach chairs, towels, 5 bikes, 2 wagons and beach toys for the kids. Sleeps 10.

Guest favourite

Cottage in Greenwood Lake

4.98 out of 5 average rating, 331 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 #32370

Guest favourite

Home in Milford

5 out of 5 average rating, 5 reviews

Seaside Paradise

Welcome to our beach house in Milford! This getaway is just a short walk from the beach, making it the perfect vacation spot for families or groups of friends. Whether you're looking to soak up the sun on the sandy shores, explore the charming town of Milford, or simply relax in a comfortable beach house, our rental is the perfect choice. We can't wait to host you and make your beach vacation unforgettable. Book now and start counting down the days until your beachside getaway!

Guest favourite

Home in Greenwood Lake

5 out of 5 average rating, 29 reviews

Greenwood Lake’s Iconic Lakefront “Icehouse”

Need a respite from the hustle and bustle of everyday life? This 4 Bedroom, 4 Bath home is located directly on the lake. Two floors of open living space with magnificent views of the lake and mountains. Families and couples can enjoy games indoors and out - with an expansive property and a chimenea fire pit and BBQ. A quick walk to Cove Castle Restaurant. 30 min drive to Legoland 20 min drive to wineries and breweries 15-20 min drive to NY Renaissance Faire PERMIT # 32043

Popular amenities for Rye holiday rentals

Stay near Rye's top sights

Playland Park29 locals recommend
The Capitol Theatre22 locals recommend
AMC Port Chester 1411 locals recommend
Marshlands Conservancy10 locals recommend
Little Thai Kitchen7 locals recommend
Costco Wholesale6 locals recommend

Destinations to explore

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