Vacation rentals in Caldwell

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Top-rated vacation rentals in Caldwell

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Top guest favorite

Home in Greenwood Lake

5 out of 5 average rating, 121 reviews

Summer is calling! 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

A charming studio cottage is nestled among trees, with a covered porch adorned by an American flag. Steps lead up to the entrance, and a wooden railing provides safety. Seasonal foliage in warm colors surrounds the area, complementing the rustic setting.

Cottage in Cortlandt

4.99 out of 5 average rating, 192 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Guest favorite

The living area features a comfortable purple sofa and armchair, arranged around a light coffee table. A flat-screen TV is mounted above a fireplace, providing a cozy focal point. Natural light filters through the windows, enhancing the inviting atmosphere of the shared space.

Townhouse in East Stroudsburg

4.89 out of 5 average rating, 179 reviews

Mountain Air - Jacuzzi, Hiking, Biking & River

Our house is just up the road from the Shawnee Mountain Ski Area. Located between Bushkill Falls and the Delaware National Recreation Area, it offers Skiing, hiking, biking, rivers, streams, and waterfalls. From Spring to Fall, easy access to kayak or canoe rentals. Numerous golf courses just minutes away. The historical town of Delaware Water Gap and Stroudsburg offers a variety of restaurants, music venues, wineries, breweries and boutiques. Best of all, we are only 75 minutes west of NYC.

Guest favorite

A wooden deck is viewed from a cozy condo, featuring a gas grill and overlooking lush green trees. Scenic mountains are visible in the distance, with a clear sky allowing natural light to enhance the tranquil outdoor setting.

Condo in Vernon Township

4.92 out of 5 average rating, 104 reviews

Mtn Creek - Bike, Hike, Golf, Legoland, NYC 1 Hour

Unwind in our freshly updated, family-friendly condo in Great Gorge Village with Mountain Creek Resort outside your door. Whether you're hitting the slopes, hiking scenic trails, biking, or golfing, adventure is right outside. Inside, enjoy a stylish, cozy retreat with brand-new furniture, plush beds, spotless bathroom, and all the comforts of home. Sleeps 6 comfortably—perfect for families or a relaxing getaway. Sip your morning coffee on the deck and soak in the peaceful mountain views.

Superhost

The spacious lakeview deck features comfortable sectional seating arranged to enjoy the serene water view. Lush greenery and trees frame the picturesque surroundings, while the dock is visible across the lake. Sunlight enhances the outdoor space, creating an inviting atmosphere for relaxation.

Home in Lehman township

4.82 out of 5 average rating, 219 reviews

⭐️⭐️ Elegant Lakeside Getaway

Come enjoy this picture-perfect lakefront estate filled with amenities and breath-taking views around every corner. This spacious home is perfect for large groups up to 10 guests with 8 memory foam beds. Relax and unwind in oversized rooms with home comforts all around. Great for entertaining with a massive kitchen & huge furnished lake view deck with BBQ. Just steps away from indoor/outdoor pools, lakeside beach, playground, and basketball courts. Close to all, with fun for every season!

Guest favorite

A fire pit surrounded by stone is illuminated by a warm glow, set within a wooded area as dusk approaches. Tall trees frame the scene, and silhouettes of rustic seating can be seen, with glimpses of the lake visible through the foliage.

Cottage in Vernon Township

4.94 out of 5 average rating, 190 reviews

Rustic Chic Lake view cottage 50 miles from NYC

Cozy lake view cottage 50 miles from NYC. Nestled in nature with swimming, fishing , hiking and biking with beautiful lake views. 5 beaches to choose from. Lovely walking or jogging around the lake, Appalachian trail nearby. Highland Lakes is a very scenic, peaceful area easily accessible. 3 of the best golf courses in the US , Mountain Creek water park and resort minutes away.Apple and pumpkin picking comes fall. Beautiful village of Warwick NY is nearby with restaurants and shopping .

Superhost

A wooden deck extends from the structure, featuring a round hot tub with an inviting wooden railing. Surrounding trees create a natural backdrop, providing privacy and a serene environment that enhances the outdoor experience.

Cabin in East Stroudsburg

4.81 out of 5 average rating, 249 reviews

BLVE Cabin - wood HotTub near Bushkill Falls

True mountain escape! The BLVE Cabin is situated near Bushkill Falls & Shawnee Mountain. The house is suited for eight people with 3 queen BDs and a sleeping couch. Open kitchen plan that connects with the living space highlighted by a beautiful electric fireplace and beautiful nature views. Main level deck with seasonal view with BBQ, outdoor TV & gas firepit. Lower level deck with Wood Burning Hot Tub. Basement with Pellet Stove & Projector. Real Wood Firepit on the side of the Cabin.

Top guest favorite

Home in Bushkill

4.97 out of 5 average rating, 135 reviews

Sweet Home Poconos

Beautiful home with plenty outdoor living area, access to pools, sport courts, lake, our own ski slopes and so much more! Within minutes of our gates there is horseback riding, zip lines, tree adventure programs, go-kart racing, Delaware River National Park, walking trails, Shawnee Ski Area. If you want to go for a drive you’ll get to Camelback, Kalahari Water Park, The Commons Outlet Mall which features over 100 designer stores. Most important, we welcome guests of all walks of life

Guest favorite

Home in Bushkill

4.93 out of 5 average rating, 138 reviews

Lakefront, Hot Tub, Pool, Gameroom, Pickleball

Olibear is your perfect spring retreat—ideal for couples, families, or anyone looking for a lakefront getaway. Tucked by the lake, our cozy home welcomes you with the Pocono scenery waking up around it. Just 5 minutes from Bushkill Falls, come explore the fresh spring scenery or relax by the indoor community pool, open weekends 12-4 PM. Hop in the private hot tub, grab a kayak, stroll the trails, or kick back by the firepit under the spring sky. Come claim your spring escape now!

Superhost

A spacious living area features a large, light-colored sectional sofa adorned with colorful cushions. A wooden coffee table sits at the center, surrounded by woven storage baskets. In the background, an open concept kitchen and dining area can be seen, with a staircase leading to the upper level.

Home in Lehman township

4.86 out of 5 average rating, 166 reviews

Cozy Family Poconos Home: Game Room, Pools,Firepit

Searching for the perfect Poconos vacation rental? Look no further — you've found it! Welcome to Golden Retreat, a family-owned escape tucked inside the gated Saw Creek Estates. This cozy 3BR/2BA home features a fully stocked kitchen, relaxing jacuzzi, and sunlit living room perfect for morning coffee. Enjoy a loft with board games, plus a full game room with billiards, ping pong, air hockey & more. Ideal for family getaways, group trips & weekend escapes to the mountains.

Top guest favorite

A circular seating area is surrounded by red Adirondack chairs arranged around a stone fire pit. Lush greenery and flowering trees are visible in the background, enhancing the outdoor space's natural ambiance.

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.

Top guest favorite

A scenic view of the river, showcasing lush green hills in the background and a collection of boats docked along the shore. A wooden deck is visible in the foreground, framed by a fence and greenery, inviting relaxation by the water.

Cottage in Sea Bright

4.95 out of 5 average rating, 133 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!