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Vacation rentals in Milton

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Top-rated vacation rentals in Milton

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

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Top guest favorite
The image shows a cozy backyard featuring a colorful hammock draped between trees, providing a relaxing view of a two-story gray house. Large windows and a deck with outdoor seating are visible, surrounded by lush greenery, creating a peaceful and inviting atmosphere.
Home in New Paltz
4.9 out of 5 average rating, 147 reviews

Fully stocked creekside sauna retreat with privacy

Welcome to Bluskyz! (Blue Skies) Perfectly nestled between the charming village of New Paltz and the beauty of the Gunks and it’s surrounding countryside. Quiet culdesac road close to everything, ONE HOUR FROM THREE MOUNTAINS and within walking distance to a couple of real country gems. Top of a hill, this home has amazing privacy, and the quiet of being the last home on a dead end street. With a natural spring pool, pergoladining, sauna in the back yard, your private spa in the Gunks awaits

Guest favorite
A spacious living area features a light-colored couch alongside a round coffee table. Sliding doors provide separation from the sleeping area, which contains a large bed dressed in light linens. Natural light filters through the nearby windows, illuminating the warm wooden floor.
Home in Milton
4.76 out of 5 average rating, 190 reviews

Historic 1 BR Family Home Near Buttermilk Falls

This historic upstate New York family home was lovingly restored by 4th generation owners. Once a 1790 Stagecoach Stop, this 1 BR home is now the perfect stay for guests visiting Buttermilk Falls Resort & Spa, coming for a wedding in the Hudson Valley, or exploring local agritourism. Enjoy our large kitchen and sitting area, 180-degree sunroom, and newly-renovated bathroom. Our home is a duplex that sits on 5 wooded acres, and the other side of the home is also available for rent on AirBnB.

Top guest favorite
A charming cabin is nestled among vibrant trees displaying autumn foliage. A wooden staircase leads to the entrance, flanked by natural stone walls. Outdoor seating arrangements are visible on the deck, offering a peaceful retreat in a wooded setting.
Cabin in Fishkill
4.96 out of 5 average rating, 126 reviews

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Top guest favorite
Home in New Hamburg
4.94 out of 5 average rating, 271 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door. We have added a separate kitchenette additional crockpot and induction cooktop.

Top guest favorite
A serene stream cascades over smooth rocks, surrounded by a wooded area filled with autumn leaves. A wooden bench sits nearby, offering a tranquil spot to enjoy the peaceful atmosphere. The gentle flow of water reflects the greenery of the trees.
Home in Rhinebeck
4.95 out of 5 average rating, 275 reviews

3Br Hilltop Ranch on 130acre farm w/ falls & creek

Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

Top guest favorite
A spacious bedroom features a large queen bed with a contrasting striped blanket. Nightstands are positioned on either side, and a lamp provides soft lighting. Two windows with light-filtering curtains allow natural light to fill the room, complemented by a beige carpet.
Guest suite in Marlboro
4.96 out of 5 average rating, 514 reviews

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

Top guest favorite
The guest house features a contemporary exterior with green paneling and wooden accents. An extensive patio surrounds the structure, furnished with lounge chairs and a dining set. Large glass doors and windows invite natural light, while views of the surrounding landscape are visible.
Home in High Falls
5 out of 5 average rating, 251 reviews

Our Place - A Big Little House

Mahali Petu is a five year old guest house situated well off the road with meadow views. It is built of high quality materials and finishes. The kitchen is fully equipped and offers custom cabinetry & granite countertops. The full bath offers a walk-in European shower with dual shower heads. There is extensive outdoor decking with seating, a gas grill, fire pit, hot tub and an outdoor shower. Peaceful and quiet, yet walking distance to High Falls restaurants and shops.

Top guest favorite
The front of the cabin is showcased with a welcoming door decorated with a wreath. Two blue chairs and one white chair are positioned on either side, complemented by a small table and potted flowers near the entrance. Lush greenery surrounds the cabin.
Tiny home in Newburgh
4.96 out of 5 average rating, 302 reviews

Cabin in the heart of the Hudson Valley, Cabin 3

Our little cabin is perfect for one or two guests for short stays while visiting local family, touring the areas wineries or nature trails, or for a clean, quiet over night stop while traveling long distances. Explore the Shawangunk Wine Trail, hike Minnewaska, sip cider at Angry Orchard, visit The Walkway Over the Hudson, or sample and shop the areas diverse farm stands and breweries. There is so much to see and do in the Hudson Valley and our cabin is close to it all!

Top guest favorite
Guest suite in Hyde Park
4.98 out of 5 average rating, 242 reviews

The Harvest Guest House~ Hidden Gem with Pool

Reconnect with yourself & nature. The Georgian style home is set on 6 wooded acres and surrounded by rugged rock ledges, minutes to Marist, The Culinary, Roosevelt & Vanderbilt estates. THE HARVEST GUEST HOUSE offers a genuine Hudson Valley stay. Your suite has its own private entrance, bathroom & fireplace. Enjoy a comfortable place to unwind after exploring nearby trails, river towns, and historic sites. Relaxed, real, and rooted in nature.

Top guest favorite
An airy room is highlighted by wooden beams and large windows that overlook greenery. A spacious bed with a patterned duvet is positioned beside a cozy bed. A round table and chairs are situated in one corner, complemented by a woven rug and a decorative basket.
Home in Rhinebeck
4.97 out of 5 average rating, 208 reviews

Honeybug Snug near Omega Institute!

Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.

Top guest favorite
A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.
Home in Livingston Manor
4.96 out of 5 average rating, 400 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

Guest favorite
Large triangular windows provide a view of the snowy landscape outside, allowing natural light to fill the space. The wood-paneled walls and ceiling create a warm ambiance, while a minimalist chandelier hangs above, adding a touch of modern design.
Guest suite in Marlboro
4.97 out of 5 average rating, 263 reviews

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.

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