Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Guest favorite

A cozy living area is displayed with warm wooden walls and a plush sofa adorned with vibrant pillows. A small green side table complements the space. A wood stove is positioned nearby, with a window allowing natural light to illuminate the area.

Cabin in Bovina Center

4.97 out of 5 average rating, 395 reviews

Delightful Cabin with Extras

Come to beautiful Delaware County and settle into serene and comfortable surroundings for a restorative getaway in any season at this lovely Bovina cabin. Enjoy the hot tub, wrap-around deck, firepit, and pristine pond on 8 acres of rolling hillside property. *Notes: While our Air BnB Plus photo shoot was taken in winter, the cabin is a fantastic year-round respite, beautiful in every season. Also - each adult beyond 2 is $25 per night, but we do not charge for children, so do not include kids in your guest # (but let us know). Inside this 2- bdrm Catskills cabin, you'll find an open living/kitchen space with comfy couches and wood stove. Outside, there's a wrap-around deck with grill and hot tub. The cabin sits mountainside on eight beautiful acres of meadows, forest, a fantastic swimming pond and a fire pit. Swimming pond, deck, grill, fire pit, outdoor hot tub, wi-fi, and great local dining and festivals. Nearby farm stands, hiking, skiing, fishing, golf, tennis, and low-key town pool (in Andes). Amazing beef cattle are just down the road, so if you'd like some for the grill, we can put it in the fridge! We live right up the road so are readily available to answer all of your questions and provide whatever we can to make your stay memorable. The cabin is on Bramley Mountain in the beautiful town of Bovina Center. Neighboring farms offer organic veggies, grass-fed meat, cheese, and milk. The town also has top-rated Catskill dining, including Brushland Eating House, Table on Ten, and the Mountain Brook Inn. We're three hours from NYC by car. A beautiful ride! Buses also run regularly from Port Authority to nearby Andes or Delhi, so if you don't have a car, we're happy to pick you up. Fully equipped kitchen, 2 bedrooms (1 queen bed and 1 full bed), blow-up bed, games, books, DVDs and video streaming access.

Top guest favorite

Home in Greenwood Lake

5 out of 5 average rating, 121 reviews

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to 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!

Top guest favorite

Home in Glen Spey

4.99 out of 5 average rating, 135 reviews

Lakehouse Getaway/Winter/Summer/Spring/Fall

Book this lakefront retreat as a romantic getaway, family vacation, or family reunion, with our sister property. Imagine, beautiful scenery, fresh air, breathtaking views, all while relaxing in our lakefront Gazebo, Our spectacular seven person Hot Spring Spa, or optional (extra charge) Bimini Top speedboat. When not spending time on the 2 acres... feels like 20 since it borders open forest, you can visit Bethel Woods, ResortsWorld Casino, Forestburgh Playhouse,Shrewd Fox Brewery Spring 2025!

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

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

4.88 out of 5 average rating, 191 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.

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.

Top guest favorite

Cottage in Livingston Manor

4.99 out of 5 average rating, 146 reviews

Cozy mountain top home - views, 5acres & a gym.

Located 2hrs from NYC, 7mins from Livingston Manor and close to Belleayre and Plattekill ski mountains. Sat atop a mountain, with 5 acres that sweep away from the property revealing stunning long distance views. Beautiful light throughout - front room with fireplace, full renovated kitchen, lounge, dining area, master bedroom, 1 large guest room, office / single bedroom, 2 bathrooms and huge covered back porch + a full home gym complete with Peloton bike, Peloton tread + ping pong table.

Superhost

A wooden dock is positioned by a calm river, surrounded by lush green trees. The vibrant foliage reflects the tranquility of the natural setting, while the water gently ripples in the foreground.

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.

Guest favorite

A quaint cottage is shown nestled among trees, overlooking Greenwood Lake. Colorful autumn foliage frames the scene, with water and distant hills visible in the background. The cottage features a dark exterior and a small path leading to a covered entrance.

Cottage in Greenwood Lake

4.92 out of 5 average rating, 88 reviews

Cottage with Picturesque Views

Quaint 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. 2 BR, 1 Bath private 2 car parking. Fenced in deck allows for scenic dining. Fire pit with Adirondack seating allows for around the fire gatherings. #CozzyCottage_GWL Town of Warwick Short Term Rental Permit # 34234

Top guest favorite

A serene outdoor deck features a centrally placed Solo Stove surrounded by five wooden Adirondack chairs. The scene captures a tranquil sunset with soft pink and orange hues reflecting off distant mountains and lush greenery.

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.

Guest favorite

A serene lakeside dock is depicted, featuring two blue adirondack chairs and a small table. A kayak and another boat are visible alongside the dock, reflecting the calm water. Foliage frames the scene, enhancing the peaceful atmosphere.

Cabin in Shohola

4.95 out of 5 average rating, 19 reviews

Rhodo - charming private lake front cabin

Relax with the whole family at this peaceful place to stay. Enjoy swimming, boating and fishing in the natural lake, barbecuing on the beach, toasting marshmallows around the fire-pit under the stars, walks in the conservatory and exploring downtown Milford's unique shops, brewery, winery and restaurants. Location is great for day trips to popular falls, national recreation areas, hikes on the AT, rafting down the Delaware river and more.