Vacation rentals in Orangeburg

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Top-rated vacation rentals in Orangeburg

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

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Guest favorite

Apartment in Greenwood Lake

4.94 out of 5 average rating, 86 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

Guest favorite

Condo in Vernon

4.96 out of 5 average rating, 56 reviews

New Luxury Ski Condo-2 Full Bathrooms

This newly renovated Great Gorge Village condo, the perfect getaway to be active or just relax with the whole family. There is so much to explore during every season. It's heaven for golfers, leaf peepers, skiers, snowboarders, hikers, bikers and water park explorers. For those looking to relax and unwind it's a great area to explore wineries, breweries and top- notch restaurants. Please note: the unit is located on the second floor. Also, the master bedroom loft suite is up a spiral staircase

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!

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.

Top guest favorite

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Top guest favorite

Condo in Vernon Township

4.94 out of 5 average rating, 145 reviews

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Guest favorite

Chalet in Glen Spey

4.9 out of 5 average rating, 132 reviews

Mayflower - Lake access/hot tub/game room/pets

Only 1 1/2 hours from NYC! Come and take in the winter beauty in the Catskills. Welcome! Everything you’d ever want in a lake community chalet! Please bring all your favorite people and enjoy our 3500ft² chalet and an acre of fenced in gorgeously landscaped grounds complete with firepit, fruit trees, fishpond, hot tub, outdoor pizza oven, ultimate game room and best of ALL a 5 minute walk down our private treelined road down to your own private 30 feet of lakefront!

Top guest favorite

Cottage in Sea Bright

4.95 out of 5 average rating, 132 reviews

Pineapple Cottage 1 Block to beach sleeps 6!

RARE Off Street Parking for 4 compact cars or 3 SUVs This 3 bedroom beach cottage is a perfect, cost effective alternative to a hotel stay. Wifi, N64, HBO, Cable & board games for those rainy days. Fully furnished bedrooms, one bedroom has home office desk set up, living area, and kitchen, to our comfortable lounge area, BBQ, and outdoor shower. Perfect way to relax after a fun day at a beach, event, or exploring the beautiful town of SeaBright!

Top guest favorite

Apartment in Long Beach

4.99 out of 5 average rating, 174 reviews

Incredible Long Beach Private Rental

True 5 star two bedroom rental. Newly renovated and professionally designed. Stunning ocean views from private second floor deck. You have your own barbecue and fully furnished outdoor space so you can enjoy the your stay on your terms. You are just a walk to the bars and restaurants of the West End. No car required! Walk or catch the bus from the train. Only 700 feet from the ocean. Due to allergies in the home we are unable to host any animals.

Guest favorite

Home in Hopatcong

4.92 out of 5 average rating, 140 reviews

Lakefront Hopatcong w/dock kayaks fishing near NYC

3800 sqt 4b 2.5b, stunning lakefront house on the largest lake in NJ. Breathtaking lake views from every room. Sunrise coffee at bedroom balcony. Grill in the sunset at the spacious patio, fishing off the private dock. two spacious living rm for multi family, well equipped kitchen, large washer dryer, 3 kayak, fishing rods, grill, everything you need for your group to have a comfortable lake retreat and make some beautiful memories. 1 hr to NYC.

Guest favorite

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.

Guest favorite

Home in Lackawaxen

4.91 out of 5 average rating, 11 reviews

Spacious, modern open concept 3bdrm in Masthope

New to market. Spacious, unique, modern home with wrap around deck, Firepit and Hammock. Amazing outdoor space with picnic table, an outdoor firepit with seating, and your very own outdoor PIZZA OVEN! The interior of the home is open concept living, dining room & kitchen. Plenty of space for a family gathering. The kitchen is fully equipped. The game room is spacious with a pool table, tv and foosball.