Holiday rentals in Surprise

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Top-rated holiday rentals in Surprise

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

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Top guest favourite
A spacious living area displays a mix of seating options, including a blue couch and two accent chairs. Natural light filters through large windows, highlighting the wooden beams above. A wooden table sits in the foreground, with a ladder leading to the loft visible in the background.
Flat in Earlton
4.94 out of 5 average rating, 312 reviews

Sweet Farm Stay

For an extra fee we also offer… ** FARM CAMP** Apr-Dec. Perfect for kids & families. 2 hours of farm chores, pony-riding, crafts every morning. Extra fee: $100/day. ** CRAFT RETREATS** All meals included. Wool/wood/kitchen craft. Work on the farm, MAKE stuff, and enjoy the outdoors. Extra fee: $250/person, min 5 people. **WRITING RETREATS** All meals included. A weekend of intensive writing + a break from internet. Extra fee: $250/person, min 5 people. Find us on ig—honeyhollowfarmstay!

Top guest favourite
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, 223 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 favourite
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, 139 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, 272 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 favourite
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, 158 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 favourite
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
4.94 out of 5 average rating, 155 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 favourite
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, 339 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 favourite
A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.
Home in Hunter
4.96 out of 5 average rating, 214 reviews

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Guest favourite
A cozy dining area features a rustic wooden table surrounded by black chairs, set against a backdrop of large windows that bring in natural light. A vintage cabinet and a cream-colored sideboard are positioned nearby, enhancing the inviting atmosphere.
Home in Catskill
4.96 out of 5 average rating, 260 reviews

Curated Design | Hot Tub | Fire Pit | Hudson:15min

Welcome to Salt Hill House — a 1940’s cottage style house that’s been beautifully renovated with modern furnishings. You’ll be able to relax on the outside deck rocking chairs with a cup of coffee and cozy up around the fire pit. The kitchen is fully stocked — from spices, coffee, baking essentials, pots/pans, to any small appliance you may need. The house is located just outside the quaint town of Leeds, 8 min from Catskill, 15 min from Hudson, and ~30 min from Windham/Hunter

Top guest favourite
A cozy seating area features a large, woven hanging chair with a white cushion and a bright green accent pillow. A textured pouf and a small side table complement the space, which is surrounded by large windows offering views of the mountains and natural light.
Flat in Freehold
5 out of 5 average rating, 354 reviews

Mountain View Retreat~Sunny Hill Golf / Skiing

Welcome to Sunny Hill Road ! We are located in a small community of private homes in an open space overlooking the mountains. This one bedroom unit has everything you need to enjoy your stay in the Catskills. Relax on the private deck or inside with amazing views from every window. The kitchen is fully equipped and ready to cook a full meal and then enjoy it in the dining room overlooking the mountains. It is quiet and restful here, amazingly beautiful in all four seasons!

Top guest favourite
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, 542 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.

Superhost
Home in East Jewett
5 out of 5 average rating, 4 reviews

Creekside Couple's Escape w/ Hot Tub Sauna & More!

Nestled beside a charming creek, our newly renovated cabin offers a peaceful escape where nature and comfort come together. Relax with your partner in the hot tub, on the covered deck, unwind in the wood-fired sauna, or sit by the fire in the gazebo. Enjoy the calming sounds of the creek and the outdoor views from every window. Discover nearby trails, quaint towns, lakes and waterfalls. Pet-friendly and ideal for couples looking for a unique getaway any time of year.

Popular amenities for Surprise holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Greene County
  5. Surprise