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Cottage vacation rentals in Middletown

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Top-rated cottage rentals in Middletown

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

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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, 189 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.

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.

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

A wooden playground structure is set on a grassy area, featuring two green slides and swings. The structure showcases an alpine roof and windows, surrounded by open fields and trees under a partly cloudy sky.

Cottage in Goshen

4.92 out of 5 average rating, 309 reviews

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.

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.

Cottage in Glen Spey

4.86 out of 5 average rating, 174 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.

A bedroom features a spacious bed adorned with soft linens, positioned beneath large, angled windows that frame views of the surrounding greenery. A stone wall adds texture, while the ceiling fan promotes air circulation. Soft lighting from bedside lamps enhances the ambiance.

Cottage in Pawling

4.98 out of 5 average rating, 119 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

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, 262 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, 166 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.

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.

Vacation rentals for every style

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Popular amenities for Middletown cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Top guest favorite

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

4.98 out of 5 average rating, 227 reviews

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

A cozy living area is highlighted by a brown sofa and a decorative area rug. A large, vibrant dinosaur costume is seen seated on the couch. A wall-mounted television displays a still image, while geometric mountain shapes are painted on the wooden wall behind.

Cottage in Tobyhanna

4.97 out of 5 average rating, 123 reviews

The Cozy Cottage w/ a private hot tub

A hot tub is nestled in a gravel area, featuring a textured exterior and steps leading up to its entry. The water is gently bubbling, indicating a comfortable temperature for relaxation.

Cottage in Greenwood Lake

4.85 out of 5 average rating, 204 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

Top guest favorite

A hot tub sits on a wooden deck surrounded by lush trees, offering privacy and a natural setting. Nearby, a cozy seating area is arranged with black chairs and a small table, providing a space to relax and enjoy the tranquil environment.

Cottage in Kerhonkson

4.99 out of 5 average rating, 167 reviews

Ye Little Wood | Cozy Forest Cottage with Hot Tub

The spacious deck is softly illuminated by string lights, creating a serene atmosphere. A jacuzzi, elegantly positioned, offers a relaxing retreat, while surrounding trees provide a sense of seclusion as night falls.

Cottage in Monticello

4.91 out of 5 average rating, 116 reviews

Lovely Cottage w/ Jacuzzi+Woodstove!

Top guest favorite

A well-appointed hot tub is situated within a shaded enclosure, featuring a partially open roof that allows natural light. Soft lighting accents the space, and a decorative sign may be seen on the wall. A nearby window has wooden blinds, enhancing privacy.

Cottage in Hawley

4.99 out of 5 average rating, 165 reviews

Hot Tub, Fire Pit, Minutes to Lake Wallenpaupack

Top guest favorite

A hot tub bubbles softly amidst a serene lakeside setting. Two wine glasses rest on the edge, reflecting the lush greenery and calm water beyond. Tall trees frame the view, enhancing the tranquil atmosphere.

Cottage in Beach Lake

4.99 out of 5 average rating, 116 reviews

Driftwood Cottage on Welcome Lake-peaceful retreat

A wooden deck is furnished with comfortable seating and a coffee table, providing a serene view of rolling mountains and a tranquil pond. The sky is filled with fluffy clouds, reflecting warm hues as the sun sets, enhancing the natural beauty of the landscape.

Cottage in Denver

4.96 out of 5 average rating, 134 reviews

Country Cottage w/ HOT TUB & Views

Pet-friendly cottage rentals

A stone pathway leads toward a quaint cottage nestled amid vibrant autumn foliage. The exterior showcases green panels and large windows, providing views of the surrounding nature. A mixture of rocks and smooth stones creates a natural border along the walkway.

Cottage in Willow

4.86 out of 5 average rating, 250 reviews

Peace Cottage

A charming tiny cottage features a front porch with white railings and hanging flower baskets. Windows are framed with black shutters, allowing natural light to shine in. The surrounding lawn is adorned with blooming flowers and greenery, creating a welcoming entrance.

Cottage in Gardiner

4.93 out of 5 average rating, 316 reviews

Tiny cottage on DiR mini farm

A charming blue cottage is set amidst lush greenery, surrounded by trees. A spacious lawn features several white lounge chairs and a stone patio with a circular table and chairs, providing a serene outdoor space for relaxation.

Cottage in Woodstock

4.88 out of 5 average rating, 126 reviews

Herb Cottage: history•art•woodstove•walk to town!

Three unique cottages are surrounded by tall trees in a lush green setting. Vibrant colors highlight the cottages, with red accents on the doors. Adirondack chairs in front provide space for relaxation amidst the natural surroundings.

Cottage in Pocono Pines

4.85 out of 5 average rating, 117 reviews

The Green Cottage at Camp Pocono Pines

A cozy reading nook is featured, with a leather armchair adorned with a soft white fur throw. A vintage-style lamp stands beside the chair, illuminating the space. A colorful area rug lies underneath, adding warmth to the neutral-toned room.

Cottage in Kerhonkson

4.91 out of 5 average rating, 182 reviews

*spring-ready* Pet-friendly private cabin!

A charming cottage is set against a clear blue sky, surrounded by a lush green landscape. The pathway leads to a welcoming entrance with steps, while a wooden fence encloses the yard, creating a sense of privacy and tranquility.

Cottage in Kerhonkson

4.95 out of 5 average rating, 144 reviews

Catskills Country Cottage

Cottage in Shohola

4.83 out of 5 average rating, 153 reviews

Modern Forest Retreat on a Tranquil HilltopSAUNA

Top guest favorite

Cottage in Roscoe

4.98 out of 5 average rating, 103 reviews

Roscoe Cottage Pet Friendly

Private cottage rentals

Cottage in Claryville

4.83 out of 5 average rating, 127 reviews

Cozy off grid cottage Big Pine trees in Catskill

Cottage in Palenville

4.93 out of 5 average rating, 155 reviews

Creekside Cottage

A heated saltwater pool is set within a gated bluestone patio, surrounded by lush greenery. The clear blue water reflects sunlight, creating a serene atmosphere. The pool area is framed by a mature tree line, providing privacy and a peaceful outdoor space.

Cottage in Kingston

4.92 out of 5 average rating, 369 reviews

Kapitan’s Cottage:Private Retreat Upstate Pets ok!

The exterior features a charming cottage with wooden siding and a welcoming entryway framed by large glass doors. The surrounding gravel driveway leads to a garage, flanked by lush greenery and trees that enhance the serene outdoor setting.

Cottage in Ulster Park

4.95 out of 5 average rating, 225 reviews

Hidden Gem Cottage — cozy escape to play or WFH

Top guest favorite

A cottage with a dark exterior is seen amidst lush greenery and trees. The structure features a pitched roof and multiple windows, allowing natural light to enter. Clear blue skies and scattered clouds create a serene backdrop, enhancing the cottage's tranquil setting.

Cottage in New Paltz

4.99 out of 5 average rating, 127 reviews

Charming Cottage Getaway

A warmly decorated living area features a grey sofa and armchair positioned around a black coffee table. A large stone fireplace serves as the focal point, with a television mounted above it. Natural light filters through the patterned curtains, illuminating the wooden floor.

Cottage in Tannersville

4.91 out of 5 average rating, 160 reviews

Mtn Rd Cottage -HOT TUB-Close 2 Camelback/Shopping

A spacious living area features vaulted wooden ceilings and skylights allowing natural light to fill the room. A mix of seating options is present, including a sofa and vintage chairs, complemented by a wooden coffee table. A media shelf housing various movies is positioned next to a television.

Cottage in Lanesville

4.95 out of 5 average rating, 185 reviews

Creekfront Cottage between Phoenicia & Hunter Mtn.

A wooden fence encloses a lush garden, featuring vibrant greenery and flowering plants. A charming cottage is visible in the background, complemented by a decorative arbor. Tall trees rise behind the garden, providing a natural backdrop to the peaceful setting.

Cottage in Great Barrington

4.92 out of 5 average rating, 248 reviews

Cottage on Scenic Road

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