Vacation rentals in Surprise

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Top-rated vacation rentals in Surprise

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

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Top guest favorite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties
4.99 out of 5 average rating, 153 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Top guest favorite
The exterior of a blue cottage is shown, set in a wooded area. A gravel driveway leads to the entrance, which features a wooden deck with steps. Lush greenery surrounds the structure, providing a serene atmosphere, while a small porch light and potted plants add subtle charm.
Home in Catskill
4.99 out of 5 average rating, 228 reviews

Athens, NY House - 1 Bedroom "Want to Get Away"?

Athens, NY Entire House - 1 bedroom Quiet Country Setting Now is a great time to escape to beautiful upstate NY. Guests have called it a very cozy cottage in the woods. It is set back off the road and a great place to get away and unwind. 10 minutes from Exit 21 on the NYS Thruway and is an easy drive to several towns on the Hudson River. They are known for their restaurants, local shops and quaint downtowns. The area features outdoor nature activities: hiking trails, boating and kayaking.

Guest favorite
A spacious bedroom features two beds with striped bedding. Natural light streams through large windows, illuminating the hardwood floor. A ceiling fan hangs above, and a dresser can be seen along one wall, providing ample storage space.
Home in Earlton
4.91 out of 5 average rating, 145 reviews

The Earlton - Spacious home w/ fireplace & firepit

Enjoy your time away in a spacious & peaceful new home in the Catskills of upstate New York. Relax & cozy up to the indoor fireplace or have fun with outdoor fire-pit with seating & dining area, great for BBQ & s’mores! Location is central to many historic sites, outdoor activities, tourist attractions & destinations. Nearby attractions include, skiing, hiking & ATV/biking trails, canoeing, boating, local organic farms, antiques & shopping. Forget your worries in this spacious & serene space.

Superhost
A warm living area is featured, showcasing wooden walls and a vaulted ceiling. Comfortable seating is arranged around a coffee table with an assortment of plants. Large windows reveal a snowy landscape, while shelves display books and decorative items.
Cabin in Maplecrest
4.93 out of 5 average rating, 277 reviews

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Top guest favorite
An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.
Cabin in Saugerties
4.97 out of 5 average rating, 167 reviews

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

Guest favorite
A historic two-story stone building is complemented by a smaller adjoining structure. Lush green lawns surround the buildings, and trees provide shade. The background showcases the Hudson River, reflecting a soft evening light with the moon rising above. Outdoor seating areas are visible along the shore.
Loft in Athens
4.93 out of 5 average rating, 162 reviews

1860's Hudson River Carriage House Loft

Carriage house apartment on grounds of historic 1600's Dutch bouwerij (farm), yet with all of the modern amenities. Our Hudson river side apartment features original exposed beams, wood floors, tasteful decor, and a complete country kitchen. On-Hudson river edge setting with beach access allows watching eagles & herons, or kayaking. Walk-in to marshland wildlife refuge. 19th century lighthouse on property. Leaf peeping or apple picking during the fall. Hunter and Windham ski areas nearby.

Top guest favorite
A modern A-frame cabin is illuminated under the evening sky, featuring large glass doors that open to a spacious deck with outdoor seating. The surrounding wooded area is visible, adding to the tranquil setting of the nature retreat.
Cabin in Freehold
4.94 out of 5 average rating, 344 reviews

Tiny Home A-Frame with Hot Tub & Creek

Just a little over 2 hours from NYC, the Cozy A-Frame is a 400 sq foot, eco-friendly, creekside cabin set in the Northern Catskills of New York. Our brand new home has been thoughtfully designed to include many indulging comforts while secluded in nature. Take in the calm of the woods from the hot tub or while roasting s'mores at the fire pit. Or turn up the music on the vintage stereo and watch the snow fall. An ideal getaway for those seeking a romantic escape or a change of pace to WFH.

Guest favorite
The jacuzzi hot tub is set on an outdoor deck, with water gently bubbling. Soft towels are neatly stacked nearby. In the background, a large tree provides shade, while vibrant foliage signals the transition of seasons in the surrounding landscape.
Cottage in Greenville
4.92 out of 5 average rating, 263 reviews

Historic farmhouse escape on 14 scenic acres

Enjoy the tranquility of King Hill Cottage, nestled in the Hudson Valley's rolling farmland just east of the Catskills. A quiet place in the country for nature lovers, friends & family seeking a peaceful sanctuary to gather and unwind. The farmhouse rests under the shade of giant maple trees, overlooking a private valley alive with an array of colorful birds and wildlife. Explore hiking, golfing, skiing, creek swims, apple picking, and strolling local Hudson Valley river towns.

Top guest favorite
A modern bungalow is illuminated at dusk, featuring large glass doors that reveal a warm interior. A spacious deck area is adorned with string lights and includes comfortable seating options, inviting relaxation amid the surrounding trees.
Bungalow in Cairo
4.99 out of 5 average rating, 550 reviews

Modern Riverfront, Swim & Fish, 20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Top guest favorite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.99 out of 5 average rating, 175 reviews

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Top guest favorite
The A-frame exterior features a steeply pitched roof and wooden siding, surrounded by tall trees. A stone pathway leads to the entrance, which is framed by two potted plants. Decorative stained glass adds a unique touch to the central door.
Cabin in Cairo
4.95 out of 5 average rating, 197 reviews

Cozy Catskill A-Frame on 4-Acres

30mins +/- to premier skiing/snowboarding at Hunter and Windham Mountains! Escape to our charming chalet-style A-Frame, nestled between the Catskills and Hudson Valley in the hamlet of Cairo, NY, minutes away from I-87. Perfect for friends, couples, or families, this cozy retreat offers easy access to Catskills hiking, quaint upstate towns, or a perfect staycation. Unwind on the expansive deck, gather around the fire pit, or cozy up inside this unique cabin.

Top guest favorite
A spacious deck extends from the house, featuring seating areas and planters with colorful flowers. A pergola offers shaded seating, while the green lawn and surrounding trees create a serene backdrop. The house's exterior displays a rustic design, complemented by large windows.
Home in Greenville
4.88 out of 5 average rating, 259 reviews

Beautiful Summer cabin, North Catskills/Greenville

The house is located in the Catskills, Greenville, NY, (Green County). I built my home in 2013 at the end of a private road surrounded by 11 acres. The house is fully furnished with all the amenities. It has a beautiful view of the Catskill mountains from a huge front deck where you can sit and relax, unwind and/or have an outdoor cookout. It is complete with a covered outdoor picnic table and lawn chairs for sunbathing or just simply relaxing.

Popular amenities for Surprise vacation rentals