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Cottage vacation rentals in Middletown

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middletown cottage rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

Superhost
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 Bethel
4.96 out of 5 average rating, 256 reviews

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

Top guest favorite
A spacious outdoor deck is seen, featuring pink lounge chairs and a small black table with a decorative item. A shaded area with a red umbrella provides relief from the sun. Lush greenery and the tranquil lake are visible in the background under a clear blue sky.
Cottage in Sterling Forest
4.98 out of 5 average rating, 127 reviews

Romantic Experience Secluded Lake House + Hot Tub

Guest favorite
The lakehouse is nestled among tall trees, with a spacious deck overlooking the water. Colorful flowers enhance the natural landscape, while a rocky shoreline leads to tranquil waters. Sunlight filters through the trees, creating dappled patterns on the house and surroundings.
Cottage in Highland Lake
4.97 out of 5 average rating, 348 reviews

The Mountaintop Lakehouse that Time Forgot.

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, 145 reviews

Driftwood Cottage on Welcome Lake-peaceful retreat

Superhost
The exterior of a charming gray cottage is shown, featuring a welcoming front door and large windows adorned with blinds. Decorative potted plants and a small seating area with pillows add a cozy touch. An American flag is displayed by the entrance.
Cottage in Glen Spey
4.86 out of 5 average rating, 180 reviews

Charming cottage with Hot Tub -PET FRIENDLY

Guest favorite
The open-plan living space features large windows offering expansive views of the rolling farmland. A comfortable gray sofa faces a wooden coffee table, while a modern TV stand holds a flat-screen television. The adjacent kitchen includes barstools at a countertop with navy cabinetry.
Cottage in North Branch
4.94 out of 5 average rating, 141 reviews

Renovated Country Cottage w/ Hot Tub & View

Guest favorite
The entrance of a cottage is framed by lush greenery, showcasing a welcoming wooden porch and a dark door. Potted plants add a touch of charm to the inviting pathway, which leads through a grassy yard.
Cottage in Boiceville
4.98 out of 5 average rating, 118 reviews

Hot Tub & Chic Catskills Woodstock Design Retreat

Superhost
The image captures a vibrant sunset over a tranquil lake, with an array of warm colors reflected in the water. Soft clouds scatter across the sky, framing the peaceful scene. The surrounding landscape features silhouettes of trees along the shore, enhancing the natural beauty.
Cottage in Bethel
4.95 out of 5 average rating, 132 reviews

Lakehouse, Sunset View, Big Deck, Hot Tub, Dogs OK

Pet-friendly cottage rentals

Guest favorite
A cozy bedroom features a spacious bed adorned with decorative pillows. Wood paneling and a macramé wall hanging create a warm ambiance. Soft curtains frame the entrance, while two bedside lamps provide gentle lighting. A comfortable chair sits nearby on wood flooring.
Cottage in Highland Lake
4.94 out of 5 average rating, 198 reviews

Rustic Chic Lake view cottage 50 miles from NYC

Top guest favorite
A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.
Cottage in Kingston
4.93 out of 5 average rating, 392 reviews

Kapitan’s Cottage Private Upstate Catskill Retreat

Guest favorite
A spacious outdoor pool area is surrounded by lush trees. The pool features a smooth blue surface, a diving board, and a water slide. A charming building with large windows and patio seating is visible in the background, providing a welcoming atmosphere for relaxation.
Cottage in Pine Bush
4.89 out of 5 average rating, 282 reviews

Seclusion and Romance - cool off in the pool!

Top guest favorite
A modern cottage exterior is shown, featuring a spacious deck that leads to a grassy area. Adirondack chairs are arranged on the deck, accompanied by a BBQ grill nearby. The cottage has a striking dark facade with a red roof and a welcoming wooden door.
Cottage in Accord
4.99 out of 5 average rating, 107 reviews

Peaceful Cottage-in Private 5-acre field

Guest favorite
The cottage is set on a spacious lawn, surrounded by trees, showcasing a well-maintained exterior with a gray facade and a gravel walkway leading to the entrance. A chimney indicates the presence of a cozy fireplace inside.
Cottage in Ellenville
4.95 out of 5 average rating, 161 reviews

Shingle Gully Cottage

Superhost
A cozy bedroom features a spacious bed adorned with an orange blanket and decorative pillows. Wall shelves display framed artwork, while light enters through a nearby window. An open doorway leads to a dining area, enhancing the inviting layout.
Cottage in Kerhonkson
4.9 out of 5 average rating, 195 reviews

*fall is here!* Pet-friendly private cabin

Guest favorite
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
4.96 out of 5 average rating, 159 reviews

Catskills Country Cottage

Top guest favorite
A charming cottage is set against a backdrop of trees and shrubs, featuring a welcoming yellow door. The front yard is landscaped with manicured grass and flowering bushes, leading to a concrete walkway that guides guests to the entrance.
Cottage in Narrowsburg
4.98 out of 5 average rating, 191 reviews

Cozy Cottage in Popular Narrowsburg

Private cottage rentals

Guest favorite
A charming front porch features two rocking chairs positioned beside a small table. Potted yellow flowers add a touch of color, while a path leading to the entrance is framed by greenery and fallen leaves, evoking a welcoming outdoor space.
Cottage in Livingston Manor
4.97 out of 5 average rating, 208 reviews

Catskills Cozy Retreat:Comfy Beds, Firepit, & More

Superhost
A green contemporary sofa is positioned in a bright living area, complemented by a wood slab coffee table. Local artwork adorns the walls, and a subtle area rug enhances the space. A doorway leads to adjoining rooms, contributing to an open layout.
Cottage in Tillson
4.97 out of 5 average rating, 156 reviews

Cozy cottage with local art

Guest favorite
A private dock extends over calm water, featuring several wooden chairs for relaxation. Lush greenery flanks the lake, with sunlight shimmering on the surface. The serene setting is complemented by a few ducks gently swimming nearby.
Cottage in Mohegan Lake
4.91 out of 5 average rating, 209 reviews

The Pearl of Westchester

Top guest favorite
A quaint cottage is nestled among trees, featuring a covered porch with a railing. Colorful seasonal flowers adorn the entrance, leading to a gravel pathway. The driveway is lined with trees and offers ample parking space, creating a serene atmosphere in a wooded setting.
Cottage in Cortlandt
5 out of 5 average rating, 208 reviews

The Little Cottage in the Woods

Top guest favorite
An open-concept space features wooden beams and large windows, filling the area with natural light. A dining table with six chairs is positioned centrally. A cozy seating area includes a sofa and armchair, while a staircase leads to the loft bedroom above.
Cottage in Rhinebeck
4.99 out of 5 average rating, 164 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

Top guest favorite
Cottage in Hawley
5 out of 5 average rating, 138 reviews

Cottage on House Pond

Top guest favorite
A modern kitchen features cabinetry in natural wood tones, complemented by a tile backsplash. Stainless steel appliances are visible, including a refrigerator, stove, and microwave. A dining table for two is set with wine glasses and simple place settings, while large windows provide ample natural light.
Cottage in Woodstock
4.95 out of 5 average rating, 221 reviews

Stunning Woodstock 1 BR Hideaway

Guest favorite
An open living area features modern furnishings, including a dark blue sofa and a light grey armchair. A neutral rug covers the floor. A kitchen area with a breakfast bar is visible in the background, along with large windows that frame views of the surrounding greenery.
Cottage in Kerhonkson
4.94 out of 5 average rating, 301 reviews

Blue Haven in the Catskills

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