Cottage vacation rentals in Monticello

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Top-rated cottage rentals in Monticello

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Guest favorite

A charming cottage exterior is framed by lush greenery, featuring dark wood siding and red shutters. A welcoming entrance is indicated by a small covered porch, with a clear view of the surrounding landscape. Gravel paths and natural stone accents enhance the inviting outdoor space.

Cottage in Lake Harmony

4.88 out of 5 average rating, 192 reviews

Cozy Cottage: Private Lake Access, Fires & Fun!

Discover the perfect lake getaway at Cabernet Cottage, ideal for small groups, families, or couples looking for a Poconos retreat with breathtaking lake views and PRIVATE access. Open-concept kitchen, dining, and living area with cozy gas fireplace to enjoy year-round. Minutes from restaurants, golf courses, ski mountains and endless lake activities nearby. Enjoy elevated views and tranquil moments at our Cottage, your ultimate haven in the heart of the Poconos. Let your adventure begin here!

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, 188 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

Top guest favorite

A peaceful waterfall cascades over rocks, surrounded by lush greenery and trees. In the background, a quaint cottage is visible beside the tranquil pond, enhancing the natural beauty of the setting. Sunlight filters through the leaves, creating a serene atmosphere.

Cottage in Warwick

5 out of 5 average rating, 213 reviews

Cottage at Millpond Falls - Romantic Luxury Escape

Looking for a romantic getaway? Relax in this cozy cottage overlooking a waterfall in a private setting. We offer a 5-star premium experience! Super-clean and luxurious. One hour from NYC. Our most frequent review: "We can't wait to come back!" Nearby wineries, craft breweries. Minutes from Warwick village, restaurants, bars, antiques, shopping, Appalachian Trail, and Greenwood Lake. Apple picking, skiing and water park nearby. Close to LegoLand and Jehovah's Witness Headquarters.

Superhost

A cozy living area features a stone fireplace framed by vintage skis. Natural light streams through two windows, illuminating a plush sofa and an armchair. A glass coffee table rests on a colorful area rug, complemented by greenery in a pot and minimalist artwork on the walls.

Cottage in Gardiner

4.9 out of 5 average rating, 161 reviews

Little Cottage Under the Ridge

Visit the cottage for an upscale retreat in the rock climbing epicenter of New York’s famous Shawangunk ridge. our mountain top paradise sits on a dead end road amongst untouched nature, only minutes to town, with a small chef’s kitchen, breakfast bar, and brand new everything. As the last property before Minnewaska’s protected preserve land, the cottage offers unmatched peace and quiet. Enjoy a private campfire beneath mature maple & oak trees that decorate our secluded five acre property.

Guest favorite

A contemporary open-concept kitchen and living area features large windows that frame scenic views. A central dining table complements the kitchen with dark cabinetry and modern appliances. A comfortable couch with decorative pillows enhances the inviting space, while a vibrant potted plant adds natural greenery.

Cottage in Greenwood Lake

4.98 out of 5 average rating, 336 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 #33593

Guest favorite

A well-maintained cottage is framed by lush green grass and tall trees. A neat path leads to the front door, which is accented by a vibrant red door. The cottage overlooks a serene lake, enhancing its inviting exterior.

Cottage in Walden

4.96 out of 5 average rating, 108 reviews

Cute, Cozy, Lakefront cottage

Cute, cozy lakefront cottage on private lake. Deck with an unobstructed view of the lake. Stunning sunrises, pinewood floors in bedroom/living room/kitchen. Queen size bed in bedroom. Situated on the same lot as owner occupied main house. Quiet, residential area. Near wineries, breweries, hiking. WIFI. No TV. Unfortunately, due to severe pet allergies I am unable to host any kind of animals including emotional support and service dogs and cats of any kind.

Superhost

A serene lakeside view is captured from a wooden dock featuring two chairs, one white and one blue. The calm water reflects the cloudy sky and surrounding greenery, creating a peaceful atmosphere. Trees line the far bank, with hints of nearby residences visible in the distance.

Cottage in Nicholson

4.85 out of 5 average rating, 119 reviews

Lakeside Cottage near skiing/waterparks/wineries

Welcoming cottage located on a private lake near skiing, golfing, waterparks, wineries, and breweries. Recently renovated with a large living/dining area perfect for relaxing and gathering with family & friends. Offers an additional loft with 2 full-size beds, great for kids. A short walking distance from a year-round bar and grill with a rotating seasonal menu and craft beer. Several other casual and fine dining options are located within minutes.

Guest favorite

Cottage in Glen Spey

4.86 out of 5 average rating, 173 reviews

Charming cottage with Hot Tub -PET FRIENDLY

Only 1 1/2 hours from NYC. Recharge with all the beauty the Catskills have to offer. Welcome to our 100 year old cabin with updates. It is 500 square feet of pure cuteness. It exudes charm while providing comforts. 3 bedrooms and a sofa allow for lots of guests. tucked away in nature, yet just a short drive to great local finds. Please note that, although this is a cottage in a lake community, this house does not have access to the lake.

Guest favorite

A snowy pathway leads from the cottage, flanked by trees on either side. Gentle, warm light from hanging bulbs illuminates the covered deck area, while a tranquil creek is visible in the background, with a soft blanket of snow covering the ground.

Cottage in Phoenicia

4.94 out of 5 average rating, 261 reviews

Charming creekside cottage in Phoenicia

Come relax in one of the prettiest places in the Catskills. Enjoy views of the Stony Clove, while sipping coffee on the wrap-around deck. The location is private and quiet, yet convenient to all the region's many attractions - hiking, skiing, antiquing, eating. When you are done exploring, enjoy a dip in one of the largest, deepest swimming holes in the area. Perfect for small families and couples. License Number: 2022-STR-AO-081

Top guest favorite

Two red Adirondack chairs are positioned on a grassy area overlooking the Upper Delaware River. Lush greenery surrounds the scene, with trees lining the riverbank and rolling hills visible in the distance under a clear sky.

Cottage in Narrowsburg

5 out of 5 average rating, 165 reviews

Upper Delaware River cottage

1930's cottage with spectacular views. Fully stocked and situated on a stretch of Upper Delaware river rapids near Narrowsburg, NY. Heat/AC system, fireplace, solo stove, barbecue and porch. There are 7 acres with river views and access . River is a couple hundred yards from cottage, lots of lawn, hammock, kayaking, lawn games, board games, hiking, fire pits, lots to do or just relax.

Superhost

A small outdoor seating area features two metal chairs and a round table, surrounded by lush greenery. The view looks out onto a calm lake, partially obscured by foliage, creating a serene and private atmosphere.

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you.

Top guest favorite

A cozy living area features a decorative brass fireplace with a television mounted above. Natural light streams in through sheer curtains, illuminating a relaxed seating arrangement, including an armchair and a coffee table. A dining area with bar stools is visible in the background.

Cottage in Philipstown

4.99 out of 5 average rating, 201 reviews

Modern Country Cottage by Bear Mountain

Wake up feeling rejuvenated in a lofted bedroom beneath a wood-paneled ceiling with skylight windows. Descend a spiral staircase into a warm kitchenette for a cup of coffee, then have a seat in an airy living room beside a brass-plated decorative fireplace. Enjoy a picnic or grill on the front lawn and explore the 4 acres of most authentic Hudson Valley landscape.

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What guests are saying

Romantic Getaway: Lovingly Restored Esopus Cottage

4.91 out of 5 average rating, 630 reviews2 weeks ago

We loved our long weekend stay at the cottage, especially that you could hear the creek from where we were staying. Very serene and gorgeous area, great location for town hopping, and the hosts Alma and James were extremely communicative and lovely. Highly recommend!

Cottage in Phoenicia

What guests are saying

Cozy home in the Village of Greenwood Lake

4.93 out of 5 average rating, 181 reviews6 days ago

Would highly recommend staying here. Will re-book if we return to Lego-Land or surrounding area. Loved that there was everything you need for a home that you don’t bring/pack (hair dryer, silverware, plates, cleaning supplies, spices etc). Quiet area with nice neighbors and really good food places (1-3 min walk away).

Cottage in Greenwood Lake

What guests are saying

The Little House

4.98 out of 5 average rating, 565 reviews5 days ago

“The little house” is a wonderful place to stay! It’s super spacious and was everything we were looking for. A quiet getaway from all the hustle and bustle. Beautiful decor and I loved the fireplace! The beds were very comfortable. There were 4 of us and we all felt at home in Glenn’s place. Will definitely put it on my favorites list and will return for future trips to the Catskills.

Cottage in Roxbury

What guests are saying

Charming Cottage Getaway

4.99 out of 5 average rating, 127 reviews3 months ago

This was our second time staying at the cottage. We had a wonderful stay over the holidays. The cottage was warm and cozy and Linda had tasteful and festive decor in every nook and cranny. We had the pleasure of meeting Linda. She is a truly wonderful person who loves what she does and it shines through in her beautiful property. So much attention to detail throughout the house. We hope to be back again soon!!

Cottage in New Paltz

What guests are saying

The Hickory Cottage - perfect!

4.76 out of 5 average rating, 623 reviews2 months ago

I had an absolutely fantastic stay at Judy and Eric’s cottage! The space was cozy, spotless, and had everything I needed for a comfortable getaway. But what truly made this experience special was their incredible hospitality. A snowstorm hit during my stay, and Judy and Eric went above and beyond by allowing me to stay extra time to ensure I was safe. Their kindness and generosity truly made a difference, and I couldn’t be more grateful. The cottage itself is peaceful and charming, with a breathtaking view into the woods that made for the perfect escape. Waking up to that scenery was one of the highlights of my stay! I highly recommend this place to anyone looking for a relaxing and welcoming retreat. Thank you, Judy and Eric—I will definitely be back!

Cottage in Accord

What guests are saying

Cozy Newly-Renovated Pocono Cottage

4.94 out of 5 average rating, 221 reviews1 month ago

The place was exactly what we needed! My friends & I had a little group trip for snow tubing and Wioletta’s place had everything we needed for a night away! We were able to get to the mountain safely / in good time and come back to enjoy games + a movie in the living room. Place was beautifully decorated and very clean with comfortable beds. Highly recommend! We will be back!! :)

Cottage in Albrightsville

What guests are saying

The River Road Cottage

4.77 out of 5 average rating, 111 reviews6 months ago

Came up for a weekend away from NYC with my husband and another couple and our two dogs. House was great and in a great location - 10 mins away from downtown New Paltz. Went to Twin Orchards on the weekend which we highly recommend. There is A LOT to do in the surrounding area!

Cottage in New Paltz

What guests are saying

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

4.92 out of 5 average rating, 308 reviews2 weeks ago

We enjoyed our stay in Virginia’s cottage. The location was great - peaceful surroundings with lovely views, 5 minutes by car to Goshen and 10 minutes’ drive to the freeway. It was tastefully decorated and comfortable. Communication with the host was excellent - with advice before our stay and help during our stay. Wouldn’t hesitate to recommend.

Cottage in Goshen

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