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Holiday houses in Monroe

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Top-rated holiday rentals in Monroe

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Top Guest favourite
An open concept living area features vaulted wooden ceilings and large windows offering natural light and forest views. A cozy sofa is positioned in front of a modern coffee table. An adjacent dining area and fully equipped kitchen complete the layout, promoting a spacious atmosphere.
Cabin in Greenwood Lake
4.99 out of 5 average rating, 129 reviews

Modern Nordic Designed Cabin

Newly designed Modern Nordic Cabin. Escape to the tranquility of the mountains and lakes. The Nordic cabin is modern with high-end finishes throughout. The open concept living area features a fireplace, waterfall shower, vaulted ceilings, and large windows that offer stunning views of the surrounding forest and lake. Getting to and from NYC is easy. There is a bus stop down the street and a train station 15 minutes away. Perfect for a convenient getaway from the city Warwick town Permit 34469

Top Guest favourite
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
5 out of 5 average rating, 138 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 favourite
Place to stay in Warwick
4.96 out of 5 average rating, 373 reviews

Luxe Penthouse Studio MainSt Warwick, SteamShower!

Relax & Indulge in our Luxe Penthouse Studio with Elevator & Parking! Beautifully furnished on Main St. in Warwick- Walk to Everything! Panoramic windows with amazing views over Warwick. Spa steam shower with bluetooth speakers, luxury bath toiletries, Heavenly King bed with Egyptian cotton linens, 65 in. HD Smart TV, reclining leather theater seats, velvet loungers convert into sleepers, fully stocked designer kitchen with all appliances, Nespresso & Keurig, coffee, tea, bottled water included.

Top Guest favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
4.99 out of 5 average rating, 126 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Top Guest favourite
A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.
Home in Greenwood Lake
5 out of 5 average rating, 216 reviews

Panoramic Lakeviews & Garden Oasis

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features hundreds of plants and a seasonal waterfall cascading into a lily pond with fish and frogs. A shaded patio offers panoramic views and a gas grill. Guests get access to a private community beach. In winter, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy living room, with exposed wooden ceilings, fireplace, smart TV, record player and board games.

Top Guest favourite
A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.
Cottage in Monroe
4.98 out of 5 average rating, 195 reviews

Cozy Lake Cottage

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets in any temps from inside or out, or coffee in the tree hut! Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕

Top Guest favourite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 130 reviews

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Top Guest favourite
A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.
Cabin in Greenwood Lake
4.96 out of 5 average rating, 482 reviews

Cabinessence -on Greenwood Lake, NY #34370

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Guest favourite
A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.
Guest suite in Chester
4.95 out of 5 average rating, 383 reviews

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–6 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.98 out of 5 average rating, 384 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic 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. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Top Guest favourite
A six-person Jacuzzi hot tub is positioned on a patio, overlooking a serene lake surrounded by trees. The bubbling water reflects the greenery, creating a peaceful atmosphere for relaxation.
Home in Greenwood Lake
4.96 out of 5 average rating, 315 reviews

Stylish Lakeside Cottage with Hot Tub

Welcome to Greenwood Lakeside Cottage, an all-season waterfront retreat on beautiful Greenwood Lake (just over an hour from NYC) surrounded by the Sterling Forest and the Appalachian Trail Corridor. No car? No problem! Conveniently located just steps away from an express bus stop with regular service to/from Port Authority. Boating, Hiking, Fishing, Skiing, Breweries, Wineries, Apple Picking, Waterfront Restaurants, Shopping, Historical Sites, Golf - all nearby (or right in the backyard).

Guest favourite
A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.
Apartment in Chester
4.98 out of 5 average rating, 161 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 15 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Popular amenities for Monroe holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Monroe

Guest favourite
Place to stay in Monroe
4.98 out of 5 average rating, 55 reviews

A-Frame Modern House w/ Private Pond

Guest favourite
Home in Greenwood Lake
4.98 out of 5 average rating, 81 reviews

World Cup Base ~ Lakeview House w/ Hot Tub & View

Top Guest favourite
Cabin in West Milford
5 out of 5 average rating, 54 reviews

Luxury Lake AFrame • Hot Tub • Sauna • Game Room

Top Guest favourite
A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.
Home in Accord
4.99 out of 5 average rating, 99 reviews

Accord River House

Guest favourite
A serene outdoor setting features a sparkling swimming pool surrounded by lush greenery. Comfortable seating areas, including deck chairs, are positioned nearby. Hammocks hang between trees, providing a relaxing retreat. Scenic views of the Hudson River and mountains enhance the tranquil atmosphere.
Home in Philipstown
4.95 out of 5 average rating, 40 reviews

Arkadia House Mid-century retreat with pool & view

Top Guest favourite
Apartment in Highland Falls
4.99 out of 5 average rating, 191 reviews

Riverview B&B 2 Miles to West Point

Top Guest favourite
Cottage in Warwick
5 out of 5 average rating, 253 reviews

Waterfall Cottage | Romantic Luxury Escape

Guest favourite
Cabin in Warwick
4.93 out of 5 average rating, 94 reviews

[Rabbit Hill Cabin] Hiking/Private/Forest view

Frequently Asked Questions

  • What are the best places to stay in Monroe?

    Stays near Monroe's downtown let guests explore shops, markets, and restaurants, while those near parks and the Heritage Trail provide quick access to nature. Residential neighborhoods are frequently suggested for a quieter retreat.

  • What are the best things to do in Monroe with kids?

    Monroe has family-friendly parks, playgrounds, and paved walking trails like the Heritage Trail. Seasonal farm activities and interactive local shops are often enjoyed by children.

  • What are some of the best things to do in Monroe?

    Explore the Heritage Trail on foot or bicycle, spend time at local parks, and browse downtown markets for handmade goods. Seasonal festivals and nearby farms also draw visitors throughout the year.

  • How is the weather in Monroe?

    Monroe has chilly winters, with January temperatures around 16–35°F (-9–1°C), and warm, humid summers, reaching 82°F (28°C) in July. Rain is possible throughout the year, so bringing layers and a light rain jacket is often suggested.

  • When is the best time to visit Monroe?

    Late spring and early fall are often recommended for comfortable weather and vibrant local events. Summer brings outdoor festivals and fresh produce, while autumn highlights changing foliage throughout the region.

  • What are the best places to visit in Monroe?

    People often explore the Heritage Trail, visit local parks, and stroll the historic downtown area with its shops and eateries. Public art installations and nearby farms contribute to Monroe’s locally rooted atmosphere.

  • What are some hiking trails in Monroe?

    Monroe has access to trails such as the Heritage Trail, frequently suggested for walking and biking, and wooded paths at local parks. Those seeking more adventurous routes often explore the nearby mountainous preserves.

  • What are some family activities we can do in Monroe?

    Families can explore community parks, visit local farms for hands-on experiences, or spend an afternoon biking along the Heritage Trail. Children often enjoy participating in seasonal events and craft workshops around town.

  • What are some of the best day trip ideas from Monroe?

    You can explore nearby wineries, scenic state parks, or local farms around the region. Charming small towns, historic sites, and outdoor recreation areas are also frequently suggested for day excursions.

  • Are there any pet friendly accommodations available in Monroe?

    Many hosts in Monroe offer pet friendly stays, especially in residential neighborhoods and near parks. Outdoor spaces around town make it easy to enjoy Monroe with your pet.

  • What are some local tips for visiting Monroe?

    Check community boards for seasonal festivals and farmers markets, as Monroe’s schedule is often lively. Locals suggest exploring the town’s trails early in the day and supporting area shops for unique crafts or produce.

  • What is Monroe known for?

    Monroe is known for the Heritage Trail, community-centered parks, and a tradition of local farming. The area has a mix of historic sites, seasonal festivals, and family-friendly activities.

  • What are the best hidden gems to explore in Monroe?

    Explore local farm stands, tranquil parks, and small-town shops that are often suggested for a quieter Monroe experience. Some visitors also discover nearby art studios and lesser-known nature preserves around the area.

  • What are the best foods to try in Monroe?

    Monroe’s dining scene features locally made bagels, classic New York pizza, and fresh produce from area farms. Apple cider and baked treats are popular, especially during the fall harvest season.

  • What should I bring for a trip to Monroe?

    Layered clothing is helpful due to Monroe's changing weather, plus comfortable shoes for walking or hiking. If visiting local farms or trails, packing a reusable water bottle and light rain jacket is frequently recommended.

  • What is the nightlife in Monroe like?

    Monroe's nightlife includes casual dining, locally owned bars, and venues with live music on select nights. Most evening spots have a relaxed, community-focused vibe.

  • What are the most popular events or festivals in Monroe?

    Monroe hosts seasonal farmers markets, outdoor concerts in summer, and fall harvest celebrations around apple season. Community parades or craft fairs also bring the town together during holiday weekends.

  • Are there family friendly vacation rentals in Monroe?

    Monroe has a variety of family friendly vacation rentals, especially in residential neighborhoods near parks and trails. Many homes offer larger living spaces and easy access to outdoor recreation.

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