Vacation rentals in Greenport

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Top-rated vacation rentals in Greenport

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Guest favorite

An aerial view of a large red house set against a backdrop of lush greenery and rolling hills. Expansive fields are visible surrounding the home, providing a sense of spaciousness and natural beauty.

Home in Old Chatham

4.96 out of 5 average rating, 25 reviews

Post and Beam Hilltop Sanctuary

Enjoy the quiet countryside/mountain views from this breathtaking private hilltop getaway. Step into our stunning vaulted Post & Beam home with central fireplace, cozy loft and spacious open floor plan that features a full wall of windows/doors to the back wrap around deck that allows for an incredible indoor/outdoor living experience with friends and family. Take advantage of our fully stocked chefs kitchen, comfy beds complete with fresh linens/towels and each bedroom has its own full bath.

Guest favorite

A wooden chair is positioned on a spacious deck, offering a view of the serene lake and surrounding greenery. A kayak is visible on the grass nearby, with the calm water reflecting the lush landscape.

Home in Athens

4.92 out of 5 average rating, 118 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite

A spacious wooden deck features a seating area with cozy chairs, a dining table, and an umbrella for shade. Potted plants adorn the space, and a grill is positioned nearby, creating an inviting area for outdoor gatherings.

Home in Woodstock

4.92 out of 5 average rating, 470 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

Superhost

Home in Roxbury

5 out of 5 average rating, 10 reviews

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

Guest favorite

Chalet in Goshen

4.89 out of 5 average rating, 141 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

Guest favorite

An icy waterfall cascades down a rocky cliff surrounded by snow-covered trees. The white and blue hues of the ice contrast with the dark rocks, while the icy terrain reflects the frosty environment. Clouds pass overhead, contributing to a serene winter landscape.

Condo in Windham

4.89 out of 5 average rating, 192 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Guest favorite

A scenic outdoor patio is highlighted, offering views of rolling hills and mountains under a clear blue sky. Sunlight bathes the green lawn, while several covered grills are positioned nearby. A glass table and chairs provide a comfortable area for relaxation amidst nature.

Townhouse in Hunter

4.91 out of 5 average rating, 79 reviews

Mountain View Catskill Escape-2 Mins to Slopes!

Enjoy the BEST LOCATION IN THE CATSKILLS with Scribner's Lodge right next door, Hunter Mountain 1 mile away, Tannersville a town over, Windham mountain 7 miles away, hiking, lakes, restaurants and breweries all around! Amazing 4 bedroom, 3 bathroom townhome with unbeatable views of Hunter Mountain. Stocked with all the essentials, multiple fireplaces, outdoor grill and a new patio! Bring your skis and snowshoes or rent skates for the winter and enjoy the shared outdoor pool in the summer.

Top guest favorite

A spacious living area features large arched windows framing panoramic mountain views. Two armchairs with bright yellow accents are positioned beside a small table, allowing for leisure and relaxation. Natural light enhances the wooden flooring throughout the room.

Home in Windham

4.96 out of 5 average rating, 25 reviews

“Amazing Mtn & Ski Slope Views “

The highest breathtaking Mtn Views in Windham w ski slope and lake views. This amazing resort like atmosphere includes a 8 person hot tub w 5 acres of tranquility ,3 outdoor firepits , walking pathways through beautiful gardens with a ski lift chair and Adirondack chairs at fire pits also a Japanese style garden with serene lake & Mtn views as well as from every room in the home. Two fireplaces and a lg bar w game rm as well as 2 living rooms w tvs. A 4 min drive to town & 6 min to slopes.

Guest favorite

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favorite

A wooden deck features a large outdoor dining table surrounded by black chairs, with an umbrella providing shade. A grill is visible in the background, and lush greenery surrounds the space. The geodome structure is prominently displayed to one side.

Dome in Monticello

4.96 out of 5 average rating, 26 reviews

007 Geodome

Looking for a vacation that will really stand out from the rest? Look no further! With a unique 007-themed interior, this geodome vacation rental with 1 bathroom is sure to make lasting memories. You can even bring your dogs along! Shred the slopes of Holiday Ski and Fun Park, just 9 miles away, or visit Bethel Woods. Kick back in the cozy interior, have an al fresco meal on the grill, or simply enjoy time with your loved ones. Book now! *Please note this is a non-smoking unit.

Superhost

A serene riverfront view showcases a calm waterway framed by lush greenery. A large rock outcrop emerges from the water's edge, while a deck with red umbrellas is visible above, offering a peaceful retreat surrounded by nature.

Home in Middletown

4.9 out of 5 average rating, 130 reviews

Riverfront! Swim, Fish, Hot Tub & Game Barn.

Fish, Tube, Hot tub and Game room! All in one property! This exquisite riverfront home has 3 bedrooms and a sleeping loft. This magical property is 7 acres on the River. Bellayre beach 15 mins and Windham mountain biking 30 mins. Hike, s’mores by the fire, hang out in the 3 season game barn equipped with a pool table and darts, have a drink in the riverside hot tub. 5 mins to retro bowling and restaurants. NO FIRST TIME RENTERS ID VERIFIED/REVIEWED RENTERS ONLY.

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Creekfront I Hot Tub I Sauna I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Looking for a restorative Upstate getaway? This Creekside gem has you covered. - HOT TUB - SAUNA - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach