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Vacation rentals in Monroe

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Top-rated vacation rentals in Monroe

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

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Top guest favorite
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, 135 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.

Guest favorite
A scenic view from the steps leading down to the backyard, showcasing a heated pool surrounded by a fenced patio and a newly installed hot tub. Lush green lawn and vibrant flowers complement the serene lake visible in the background, providing a tranquil outdoor atmosphere.
Home in Monroe
4.96 out of 5 average rating, 141 reviews

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

Top guest favorite
Home in Greenwood Lake
5.0 out of 5 average rating, 224 reviews

Panoramic Lakeviews & Lush Garden | Beach Access

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.

Guest favorite
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
4.99 out of 5 average rating, 204 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 favorite
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, 496 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 favorite
A comfortable living area is created with two armchairs positioned around a circular glass table. A wood-burning fireplace adds warmth, with flames visible in the hearth. Natural light filters through the window, highlighting a modern kitchen bar with high stools in the background.
Home in Monroe
4.92 out of 5 average rating, 64 reviews

3 BDR Cottage (Hudson Valley Cottage)

The Escape Cottage is a three-bedroom cottage in the Middle Hudson Valley on 3.6 acres of land. This calming getaway is located 45 minutes from NYC. It’s a romantic, cozy cottage engulfed by nature, allowing you to witness the Hudson Valley at its best. We're located 12 mins from Woodbury Commons, 19 mins from Valley Rock Inn, 20 mins from Legoland, 8 mins from Arrow Park, 19 mins from Blooming Hill Farms and less than 35 mins from Mt. Peter Ski Area, Mountain Creek Resort and Ski Campgaw.

Superhost
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
4.94 out of 5 average rating, 400 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 favorite
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
4.97 out of 5 average rating, 391 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 favorite
A classic blue farmhouse with white trim has a symmetrical facade featuring double-hung windows and green shutters. The entrance is marked by a red door, flanked by two matching red containers. A spacious lawn surrounds the structure, accentuating its inviting presence.
Home in Chester
4.98 out of 5 average rating, 163 reviews

The Little Green Farmhouse

Built in the mid 1800s, this 2,400 square foot. 2 story farmhouse is a comfortable country getaway with space for the whole family. Nestled on 2.5 acres, the house is perfectly positioned between the villages of Warwick and Sugar Loaf. There are 4 bedrooms on the 2nd floor with the ability to sleep 8 people. There are also 2 full bathrooms, a dining room, living room, office space, fully equipped kitchen, and a bonus space with a table to play board games, cards or puzzles.

Guest favorite
A sandy beach area leads to a wooden dock extending over calm waters, with a small boat anchored nearby. Two green lounge chairs are positioned on the sand, providing a serene view of the lake surrounded by trees reflecting autumn colors in the background.
Home in Monroe
4.96 out of 5 average rating, 57 reviews

Gorgeous 5BR lakefront home, private beach & dock

You'll have a great time at this tranquil, charming getaway, located only 1hr outside of the city. Come relax with amazing views of the lake, nature and surrounding woods. The property is prefect for large families or two families coming together for a vacation. Enjoy kayaking, paddleboarding and swimming right in the backyard, or bird watching from the dock. This 5BR house is a perfect weekend getaway located only 10 min to Legoland, Harriman State Park and Woodbury Commons.

Guest favorite
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
4.97 out of 5 average rating, 183 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.

Guest favorite
A spacious outdoor area features a large swimming pool surrounded by a paved patio. The villa, with a red-tiled roof, stands in the background amidst lush greenery. Sun loungers are arranged at the pool's edge, inviting relaxation.
Villa in Monroe
4.94 out of 5 average rating, 70 reviews

Mediterranean villa •pool•hot tub•fire place

Discover the Mediterranean Villa, a stunning 5-bedroom, 4-bath luxury retreat nestled in the scenic Hudson Valley. This Monroe, NY escape offers elegant interiors, a cozy wood-burning fireplace, outdoor fire pit ,Smart TVs, a private hot tub, spacious living areas designed for comfort and style. Perfect for families or groups, it’s minutes from Catskills trails, Woodbury Commons shopping, and Legoland. Unwind, explore, and indulge in upscale relaxation year-round.

Popular amenities for Monroe vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Monroe

Top guest favorite
A spacious living area is illuminated by natural light streaming through large windows, showcasing views of the surrounding greenery. A large sectional sofa is positioned in front of a stone fireplace, accompanied by a coffee table and decorative poufs.
Home in Chester
4.97 out of 5 average rating, 70 reviews

Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC

Superhost
An aerial view captures a spacious backyard featuring a fenced-in heated pool and hot tub. Surrounding the area are lounge chairs on a sun deck, a shaded gazebo, and landscaped gardens, creating an inviting outdoor retreat. The home is visible in the background.
Home in Harriman
4.87 out of 5 average rating, 83 reviews

The Hudson Hideaway~Pool, Hot Tub, Sauna~1hr toNYC

Guest favorite
Home in Monroe
4.97 out of 5 average rating, 31 reviews

Hudson Valley Getaway/West Point/Woodbury/Legoland

Guest favorite
A rustic stone house is set within a wooded landscape, featuring a gabled roof and a front porch with large windows. The entrance is marked by a green door, complemented by a white door on the side. Bare trees surround the property, suggesting a tranquil atmosphere.
Home in Chester
4.75 out of 5 average rating, 87 reviews

Stone Sanctuary

Guest favorite
Place to stay in Monroe
4.98 out of 5 average rating, 64 reviews

A-Frame Modern House w/ Private Pond

Top guest favorite
A two-story home with a light-colored exterior and burgundy shutters is set against a clear blue sky. The well-maintained lawn features manicured shrubs and trees, enhancing the inviting curb appeal. The entrance is framed by steps leading to the front door, creating an approachable feel.
Home in Chester
5.0 out of 5 average rating, 56 reviews

4 Bedroom Home with Hot-Tub

Guest favorite
Home in Greenwood Lake
4.98 out of 5 average rating, 86 reviews

Lakeview House ~ Hot Tub, Firepit, Stunning Views

Superhost
A lakefront bungalow is positioned alongside calm waters, reflecting the surrounding greenery. A private dock extends into the lake, with several lounge chairs arranged for relaxation. The property is framed by trees and landscaped gardens, illustrating a serene outdoor space.
Home in Greenwood Lake
5.0 out of 5 average rating, 31 reviews

Starlight on the Lake

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.

Destinations to explore