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Holiday houses in Greenwich

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Top-rated holiday rentals in Greenwich

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

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Cottage in Greenwood Lake

4.85 out of 5 average rating, 185 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

Just a little more than an hour away from NYC and a 4-min drive to the lake, this pet-friendly private retreat offers a hot tub, family room, spacious yard with fire pit, and a deck with a grill and comfy seating. The renovated interior has all the comforts of home including a full kitchen & streaming capabilities. Incredible perks include complimentary lake access at nearby beach, family board games, children's books, toys & a mini game table for ping-pong, air hockey, football & billiards!

Guest favourite

Apartment in Greenwood Lake

4.94 out of 5 average rating, 77 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

Guest favourite

Home in Greenwood Lake

5 out of 5 average rating, 112 reviews

Time to escape to the lake!Hot-tub/1 hour from NYC

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 178 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 Greenwood Lake

5 out of 5 average rating, 43 reviews

Explore a Luxurious Lakefront Dream Home

Discover your luxury haven on the serene shores of Greenwood Lake. Boat, swim, kayak, and bask in summer's glory. Fall brings vibrant foliage and fireside coziness. Winter offers skating in the frozen lake and skiing in the nearby mountains while spring blooms with its incredible beauty. Your perfect getaway, where modern comfort meets natural beauty. A quick 45-minute escape from the city with super high-speed internet for your work needs. Book now for an unforgettable escape! Permit N. 23-225

Home in Poughkeepsie

4.76 out of 5 average rating, 123 reviews

Newly Renovated & Comfortable Home-Vassar/Marist

Leave the busy city and the hustle and bustle behind. Relax and rejuvenate yourself in the Hudson Valley. This retreat has all the amenities (fully equipped kitchen, spacious deck/backyard, fire pit, grill, and parking on premises available). Take a walk or bike ride at the Hudson Valley Rail Trail, hike at Mt. Beacon, explore Dutchess Wine Trail c/o Clinton Vineyards, shop at the Poughkeepsie Galleria, or relax at Hand and Stone Massage. There is so much for you, family and friends to do.

Guesthouse in Milford

4.92 out of 5 average rating, 203 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

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.

Holiday home in Elmont

4.83 out of 5 average rating, 77 reviews

Lovely 2-Bedroom Elmont Apartment (Lower Level)

Enjoy this centrally-located lovely full 2-bedroom private lower level apartment. With 2 Queen sized beds, this space can host up to 4 people comfortably. Ideal for travelers or families visiting NY. Located in a quiet neighborhood. In the center of many shops, restaurants, highways. This apartment is located 7 minutes away from the USB Arena, 10-15 minutes away from JFK airport, and in close proximity to Roosevelt Field Mall and Green Acres Mall. The next adventure is never too far away!

Guest favourite

Cottage in Greenwood Lake

4.98 out of 5 average rating, 325 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 New Fairfield

4.92 out of 5 average rating, 109 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Guest favourite

Apartment in Long Beach

4.99 out of 5 average rating, 172 reviews

Incredible Long Beach Private Rental

True 5 star two bedroom rental. Newly renovated and professionally designed. Stunning ocean views from private second floor deck. You have your own barbecue and fully furnished outdoor space so you can enjoy the your stay on your terms. You are just a walk to the bars and restaurants of the West End. No car required! Walk or catch the bus from the train. Only 700 feet from the ocean. Due to allergies in the home we are unable to host any animals.

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Popular amenities for Greenwich holiday rentals

Free parking on premises

Air conditioning

Stay near Greenwich's top sights

Chipotle Mexican Grill111 locals recommend

The Cheesecake Factory60 locals recommend

Whole Foods Market54 locals recommend

Barcelona Wine Bar51 locals recommend

Stamford Town Center34 locals recommend

Playland Park29 locals recommend

Other great holiday rentals in Greenwich

Guest favourite

Apartment in Wallkill

4.94 out of 5 average rating, 140 reviews

Log Cabin Apartment Great for Outdoor Enthusiasts

Cabin in Shirley

4.86 out of 5 average rating, 139 reviews

A-Frame cabin with private beach & epic sunsets

Guest favourite

Home in Bayonne

4.94 out of 5 average rating, 16 reviews

The Rainforest I|Sleeps 12|20m to NYC|Free Parking

Guest favourite

Home in East Patchogue

4.79 out of 5 average rating, 149 reviews

Bay's Edge Vacation Get a Way

Guest favourite

Home in Chester

4.96 out of 5 average rating, 100 reviews

Millionaire Mansion Countryside Stay w/ Lrg Hottub

Guest favourite

Cabin in Rocky Point

4.89 out of 5 average rating, 455 reviews

Great little place just for a couple

Guest favourite

Home in Woodmont

4.98 out of 5 average rating, 42 reviews

Beachfront paradise- come, stay, relax!

Guest favourite

Home in Bayport

4.83 out of 5 average rating, 161 reviews

Exquisite spacious waterfront all modern-sleeps 8

Quick stats about holiday rentals in Greenwich

Total rentals
290 properties
Total number of reviews
10K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
180 properties have a dedicated workspace

Destinations to explore