Cottage holiday rentals in Monticello

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Top-rated cottage rentals in Monticello

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Guest favourite
A dining area features a wooden table surrounded by two chairs. Natural light enters through two windows covered with bamboo shades. Wall art and photographs add character to the space, complemented by a vase filled with decorative branches at the table's center.
Cottage in Monticello
4.9 out of 5 average rating, 148 reviews

Cozy Catskill Getaway Upstate NY - 5 min to casino

Kick back and relax in this cozy styled cottage! Centrally located near shopping plazas including Shoprite, Walmart and Marshalls. Also close to eateries, fast food restaurants, and Resorts World Casino. Explore the Catskills and come back to stay in a warm cottage. Although it is centrally located, it's pushed back enough that you still get the country living feeling. Located on 2 acres of land, you're sure to hear the birds chirping! There is a pull out couch available for an additional guest.

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, 117 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 hot tub is surrounded by lush greenery and illuminated by string lights, creating a serene outdoor setting. A stone path leads to the hot tub, with red chairs visible nearby, all nestled within a wooded area.
Cottage in Mongaup Valley
4.96 out of 5 average rating, 283 reviews

Hot Tub, Playground, 3 Acres, and Much More!

Relax with the whole family at this peaceful cottage in the trees 5 minutes from Bethel Woods - check out their upcoming events! Recently renovated cottage with hot tub, an electric fireplace, washer and dryer, dishwasher, and smart TVs. Family-friendly features include a baby gate, potty training seat, high chair, toddler-safe bunk beds, and toys Outdoor features include 2 fire pits, trampoline, jungle gym, basketball hoop, walking path, stream w/ waterfall, and 3 acres of woods to explore

Top guest favourite
The exterior of the cottage is set against a backdrop of lush greenery, with a spacious two-story design featuring a welcoming front porch. The surrounding landscape features a slope of vibrant grass leading towards the cottage, enhancing the serene rural setting.
Cottage in Monticello
4.98 out of 5 average rating, 144 reviews

Dutchhillcottage, gem in the southern Catskills.

Just 85 miles from NYC! Rustic chic design cottage waiting for you and your friends or family to enjoy. Private, comfy & cozy country getaway with amazing views situated on 10 acres of rolling hills in the southern Catskills, perched on a peak at the forests edge with expansive views all the way down to the Never Sink river with beautiful suntset views from our huge deck. Plenty of ameneties. Petdog friendly. Just 2 miles down the road from newly updated Holiday Mountain Ski Resort!

Top guest favourite
The living room features a spacious couch, modern lighting, and a wood-burning fireplace, with a flat-screen TV mounted above a decorative white wall. Large windows invite natural light, while sliding glass doors open to the deck. A minimalist chair adds an additional seating option.
Cottage in Monticello
4.94 out of 5 average rating, 396 reviews

Modern Upstate Escape with Outdoor Sauna

Newly renovated two bedroom, two bath cottage with four person barrel sauna at Swinging Bridge Reservoir, Sullivan County's largest motorboat lake. Updated amenities and mid-century and modern furniture provide a welcome respite from the city just 90 miles away. Take in the local scenery, catch a show at the Forestburgh Playhouse or stop into some of the local vineyards and restaurants. For a low key weekend, hang out by the fireplace playing some records and cooking a meal.

Top guest favourite
The exterior of a blue farmhouse cottage is shown, featuring a metal roof and a welcoming front porch with two white chairs. Lush green grass surrounds the house, complemented by blooming hydrangeas and decorative potted plants. Trees and open land are visible in the background.
Cottage in Grahamsville
5 out of 5 average rating, 105 reviews

“Green Meadow Cottage”, updated 1850’s farmhouse.

Relax with friends or family in this cozy updated 19th century farmhouse cottage set on 5 acres surrounded by pasture and forest. This is truly a rural setting to enjoy the serenity of nature. Centrally located, a leisurely country drive will take you to quaint towns, spectacular hiking, fine dining and more. Visit our many breweries and distilleries or just take a drive and explore. Bring your bikes and ride the gently rolling wooded roads… or not. It’s your vacation.

Guest favourite
A spacious jacuzzi is set on a wooden deck, surrounded by nature. The water's vibrant blue color reflects the sunlight. Nearby, comfortable black wicker seating can be seen, perfect for relaxing while enjoying the views of the trees.
Cottage in Monticello
4.91 out of 5 average rating, 161 reviews

Lovely Cottage w/ Jacuzzi+Woodstove!

Nestled in the hamlet of Smallwood, only 2 hours from NYC, this newly renovated cottage is the perfect getaway from the city and an oasis surrounded by nature. This cottage is perfectly located for access to surrounding lakes and seasonal beaches, hiking trails as well as exploring and discovering the lovely Catskills region. The cottage features a wood stove, spacious deck, a fire pit as well as an all-season jacuzzi to enjoy day or night.

Top guest favourite
A charming 1930's cottage is set against a backdrop of vibrant autumn foliage. The structure is surrounded by a spacious lawn, leading to glimpses of the river nearby. Brightly colored leaves adorn the trees, contributing to the serene and natural atmosphere.
Cottage in Narrowsburg
5 out of 5 average rating, 193 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.

Guest favourite
A bright and airy living area features wooden beams and a light color scheme. A gray sofa is positioned beside a small wooden table, and a chair is nearby. A patterned rug adds warmth to the space. Natural light streams in through a window, complementing the welcoming ambiance.
Cottage in Swan Lake
4.92 out of 5 average rating, 103 reviews

Catskills Tiny Home Near Bethel Woods

Take it easy at this cozy and tranquil getaway. Experience your favorite musician less than 10 minutes at the historic site of Woodstock, the Bethel Woods Performing Arts Center. Enjoy a sunset dinner at Kauneonga lake. Go boating and fishing at White Lake and Lake Superior. Take an exhilarating trip down the Delaware.

Guest favourite
The exterior of a two-story house is shown, featuring a stone foundation and white siding. A front deck with a staircase leads to a seating area with red chairs. Green trees surround the structure, enhancing its natural setting.
Cottage in Ellenville
4.88 out of 5 average rating, 370 reviews

Lake house

This house has a beautiful lake view. With boat access nearby. Nice, quiet, wooded area at the bottom of the Catskills. Near Monticello, Middletown, Kingston, Woodstock and Newpaltz. For security purposes, we can only accept reservation request from a verified profile in Airbnb. Thank you for understanding.

Top guest favourite
A serene view of the lake is presented, with gently rippling water reflecting the sky. A flagpole stands proudly beside the water, surrounded by lush greenery. A cozy seating area with a bench and lanterns is visible, offering a peaceful spot for relaxation.
Cottage in Godeffroy
4.99 out of 5 average rating, 149 reviews

Lakefront House w/Private Dock, Fire Pit & Hot Tub

Cozy and recently renovated 1940s lakefront house right on the water. Enjoy views of the lake all around the house. Private dock, fire pit, and cedar hot tub. Under 2 hours from NYC, and 20 minutes to nearby shopping and restaurants as well as great hiking trails. High speed Internet and TV provided.

Guest favourite
Large windows frame a stunning view of Kauneonga Lake during sunset, with colorful hues reflecting on the water's surface. A pair of chairs is positioned nearby, offering a cozy space to enjoy the serene scenery.
Cottage in Kauneonga Lake
4.89 out of 5 average rating, 114 reviews

Lakeside Cottage on White Lake

This lovely cottage rests on the shore of the beautiful Kauneonga Lake. The newly renovated interior creates a warm and relaxing space to take in the amazing sunset views over the lake. Right next door to Restaurant Row and just a few minutes away from the Historic Bethel Woods Center for the Arts.

Popular amenities for cottage rentals in Monticello

Quick stats about cottage rentals in Monticello

  • Nightly prices starting at

    Monticello holiday rentals start at £81 per night before taxes and fees

  • Verified guest reviews

    Over 270 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Monticello rentals

  • 4.8 Average rating

    Monticello stays are highly rated by guests – averaging 4.8 out of 5!

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