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Cottage holiday rentals in Middletown

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Top-rated cottage rentals in Middletown

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Superhost
A rustic wooden chair overlooks a calm pond, with stones encircling a small fire pit. In the distance, among trees, a cozy cabin is visible, set against a vibrant sunset sky transitioning from warm hues to twilight.
Cottage in Milford

forest cottage 1880s

A historic cabin set in the forest with a private lake. It is only a few mins away from the beautiful town of Milford, PA. You can either pet with my animals , fishing, boating in the private lake , enjoy the serenity of nature or get out and explore. hiking, skiing at Shawnee, white water rafting on the Delaware Rive. horseback riding in the state park, shopping in WoodburyOutlets and various restaurants around. Whatever you choose, this house is a great pick for the nature lover in everyone!

4.86 out of 5 average rating, 436 reviews
Top guest favourite
Cottage in Warwick

Waterfall Paradise | Romantic Cottage | Firepit

<b>Escape to your private waterfall cottage!</b> The Cottage at Millpond Falls is perfect for couples seeking a romantic, five-star retreat just one hour from NYC. ✅ Comfy queen bed & super-clean luxury linens ✅Crackling fire pit by the falls ✅ Minutes to wineries, breweries & trails ✅ Nearby adventures: skiing, lake fun, orchards ❤️ SUPERHOST • Our most frequent review: "The best AirBnb experience we’ve ever had, can't wait to come back!" Book your dates while they’re open.

5.0 out of 5 average rating, 258 reviews
Top guest favourite
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

The Mountaintop Lakehouse that Time Forgot.

Quiet Private lakehouse set down on 2 rare rock bluffs giving you a majestic water view just like it was in 1939. Extra Lg Great room w a huge fireplace. The great kitchen surrounds the chef. Big hot tub, Rowboat with canopy, 8 kayaks, Treehouse, Neverending Lakeside windows, docks, 1 hr from Manhattan w Eagles & vast wildlife like you were in the deep woods. Clean, unspoiled lake full of fish. Never had gas motors. A Mountaintop lake above the ski area. Stargazing! Perfect for get-togethers.

4.97 out of 5 average rating, 390 reviews
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

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #P25-0805 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, 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.

4.99 out of 5 average rating, 135 reviews
Guest favourite
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

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🐕

4.99 out of 5 average rating, 205 reviews
Top guest favourite
Two kayaks, colored yellow and orange, rest on the grassy shore of a serene lake. A small dock extends into the calm water, reflecting the colors of a sunset sky. Trees line the horizon, completing the tranquil lakeside setting.
Cottage in Livingston Manor

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Glass House! Here are a few things I think you’ll especially enjoy about the house. Highlights – You’ll love the: Peaceful waterfront setting – tucked away on the lake, yet just minutes to town Year-round hot tub – the perfect way to unwind after hiking, or exploring Family-perfect layout – two spacious levels with a game/media room and screened porch Kayaks & life vests – easy, safe access to the water for all ages

5.0 out of 5 average rating, 110 reviews
Top guest favourite
The cottage is surrounded by lush green grass and mature trees, offering a serene outdoor setting. A well-maintained pathway leads to the inviting entrance, while the structure features light-colored siding and large windows, creating a seamless connection with nature.
Cottage in Goshen

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

4.92 out of 5 average rating, 346 reviews
Guest favourite
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

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

4.97 out of 5 average rating, 391 reviews
Guest favourite
A modern dining area features a wooden table surrounded by stylish chairs. Five pendant lights hang above the table, providing soft illumination. A plant stands nearby, contributing to the fresh ambiance, while a sliding door offers access to outdoor space.
Cottage in Pine Bush

Modern 3BR BoHo Retreat/Nearby Hiking, Wineries

Our newly modern bohemian cottage (aka Green House!) is perfect for your next weekend getaway or a new WFH locale. Decompress from city stress in this calm, serenely appointed private home. Close to attractions but far enough away to escape, you'll never want to leave. NYC: 79 mi. Hunter Mountain Ski Resort: 60 mi. Pine Bush - groceries/supplies: 7 mi. Middletown - shopping (Walmart, Target, Best Buy, Home Depot): 16 mi. Hiking trails: 7 mi. Horseback riding: 7 mi. Sky diving: 15 mi.

4.93 out of 5 average rating, 133 reviews
Top guest favourite
The cottage is nestled among vibrant autumn trees, with golden and green foliage surrounding it. The exterior features a spacious porch along the front, providing an inviting space for guests to enjoy the natural landscape.
Cottage in Monticello

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!

4.98 out of 5 average rating, 157 reviews
Guest favourite
A cozy living room features a stone fireplace surrounded by plush seating. Wooden beams accent the ceiling, enhancing the rustic charm. Soft light glows from nearby rooms, creating a warm and inviting ambiance. Decor elements reflect nature-inspired design, adding character to the space.
Cottage in Kerhonkson

Cozy Cottage | Sauna + Stone Patio w/ Firepit

Escape to a serene cottage nestled on the Shawangunk Ridge. Unwind by the fireplace, soak in the private infrared sauna (with direct patio access), or relax outside on the natural stone terrace with a firepit and forest views. Crafted with care—from a 100-year-old reclaimed wood dining table to a curated “meaningful library” and hidden messages—this space invites calm, curiosity, and connection. Near trails, lakes, and local adventure. Thoughtful, cozy, and quietly unforgettable.

4.82 out of 5 average rating, 1020 reviews
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

“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.

5.0 out of 5 average rating, 117 reviews

Popular amenities for cottage rentals in Middletown

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

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

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

4.97 out of 5 average rating, 305 reviews
Top guest favourite
The inviting exterior of a cozy cabin is surrounded by lush greenery, with warm lights illuminating the covered porch. A fire pit is featured at the forefront, surrounded by four Adirondack chairs, creating a welcoming space for evening gatherings.
Cottage in Kerhonkson

Ye Little Wood | Cozy Forest Cottage with Hot Tub

5.0 out of 5 average rating, 250 reviews
Top guest favourite
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 Greenwood Lake

Secluded Lakeview Escape with Hot Tub

4.98 out of 5 average rating, 152 reviews
Superhost
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

Lovely Cottage w/ Jacuzzi+Access to Nearby Lakes!

4.91 out of 5 average rating, 174 reviews
Top guest favourite
Cottage in Beach Lake

Peaceful Lakeside Retreat-Easy Drive from NYC & NJ

4.99 out of 5 average rating, 188 reviews
Top guest favourite
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

Catskills Woodstock Design Retreat w/ hot tub

4.97 out of 5 average rating, 138 reviews
Guest favourite
Cottage in North Branch

Catskills Cottage w/ Hot Tub & View

4.95 out of 5 average rating, 147 reviews
Top guest favourite
Cottage in Jeffersonville

Catskills Memories · Hot Tub·Sauna·Fire Pit·Vinyl

4.98 out of 5 average rating, 108 reviews

Pet-friendly cottage rentals

Guest favourite
Cottage in Napanoch

Mid century house on 100+ acres…

4.82 out of 5 average rating, 103 reviews
Guest favourite
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

Shingle Gully Cottage

4.94 out of 5 average rating, 177 reviews
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

Upper Delaware River cottage

5.0 out of 5 average rating, 205 reviews
Guest favourite
Cottage in Kerhonkson

Beautiful stream side cottage in the woods

4.89 out of 5 average rating, 272 reviews
Top guest favourite
Cottage in Kerhonkson

Catskills Country Cottage

4.96 out of 5 average rating, 172 reviews
Guest favourite
A charming historic cottage is surrounded by lush greenery, featuring a combination of dark wood siding and green trim. Stairs lead to the entrance, while an American flag decorates the exterior. The peaceful setting provides a glimpse of nature and a sense of tranquility.
Cottage in Branchville

Historic Gem in Culver Lake. (Branchville NJ)

4.97 out of 5 average rating, 106 reviews
Guest favourite
A light-colored cottage exterior features large glass doors, surrounded by trees displaying vibrant autumn colors. A stone pathway leads to the entrance, with a lantern and potted plants adding a welcoming touch. A picnic area is visible in the yard, set against the beautiful natural backdrop.
Cottage in Philipstown

Modern Country Cottage by Bear Mountain

4.97 out of 5 average rating, 227 reviews
Guest favourite
A wooden deck extends from the cabin, featuring a round table with two transparent chairs. The view includes a forest of bare trees under a setting sun, casting warm light across the space.
Cottage in Rhinebeck

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

4.93 out of 5 average rating, 360 reviews

Private cottage rentals

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

Modern Upstate Escape with Outdoor Sauna

4.94 out of 5 average rating, 413 reviews
Guest favourite
A serene lakeside view is captured, featuring lush greenery and colorful plants in planters. A lounge chair is positioned on the grass, inviting relaxation while looking out over the calm waters of the lake, framed by a backdrop of tree-covered hills.
Cottage in Monroe

Hudson Valley Lakefront Cottage | Nature Escape

4.96 out of 5 average rating, 120 reviews
Top guest favourite
A charming cottage exterior is showcased, featuring natural wood siding and large windows. Lush greenery surrounds the building, with vibrant flowering shrubs in pink and red blooming nearby. A welcoming porch with a purple door offers a glimpse of the inviting ambiance that awaits inside.
Cottage in Clintondale

Old Mill Cottage - Upstate Mountain Views

4.97 out of 5 average rating, 404 reviews
Guest favourite
The cottage is nestled among tall trees, with natural rock formations in the foreground. The structure features a combination of brown siding and large windows, providing a blend of indoor comfort and outdoor scenery. A grassy area extends around the property.
Cottage in Cold Spring

Cheerful Private 3 Bedroom Cottage in Cold Spring

4.93 out of 5 average rating, 190 reviews
Guest favourite
Cottage in Livingston Manor

Mid-Century Cottage | Lovely Yard | Fast Wifi

4.97 out of 5 average rating, 230 reviews
Top guest favourite
A lakeside patio is equipped with a circular table surrounded by four chairs and two loungers. A stone fireplace stands nearby, offering a warm gathering spot. The serene lake reflects the greenery of the surrounding landscape and is accessed by a wooden dock.
Cottage in West Milford

Lakefront Getaway : Mountain & Lake views

4.95 out of 5 average rating, 347 reviews
Guest favourite
A private dock extends over the calm lake, featuring several Adirondack chairs arranged for seating. The cottage, with large windows, showcases an inviting glow from within, surrounded by lush greenery and trees. Soft exterior lighting enhances the tranquil atmosphere.
Cottage in Ferndale

Heron's Hideaway: Stylish Lakefront 5 BR Home

4.96 out of 5 average rating, 120 reviews
Top guest favourite
The exterior of the cottage is surrounded by colorful autumn foliage, featuring a warm-toned facade with white window frames. Adirondack chairs are placed in the foreground, and a stone fire pit is visible. Bright blue skies contribute to a serene atmosphere.
Cottage in New Paltz

Renovated Schoolhouse-120-Acre Farm

4.95 out of 5 average rating, 296 reviews

Destinations to explore