
Cottage holiday rentals in Middletown
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Top-rated cottage rentals in Middletown
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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, 439 reviews
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, 260 reviews
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, 391 reviews
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, 138 reviews
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, 208 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 #P25-0245
4.97 out of 5 average rating, 394 reviews
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
Mid-Century Cottage | Lovely Yard | Fast Wifi
Stylishly designed mid-century retreat surrounded by nature • Livingston Manor & Jeffersonville 12 min •. Bethel Woods Center for the Arts 17 min. • Great for couples or small families • Walnut Mt. hiking 8 min. • Gas grill & fire pit • Rocking chair front porch • 2 queen bedrooms, open living area, 1 bathroom. • Fully-stocked kitchen/beautiful cabinets and open shelves. • Relax inside or explore the backyard's natural beauty. •. Enjoy fast internet Your unique escape awaits!
4.97 out of 5 average rating, 231 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!
4.98 out of 5 average rating, 158 reviews
Shingle Gully Cottage
Shingle Gully Cottage is located on over 40 acres of privately-owned land bordering Sam’s Point Preserve. The cottage is located on the outskirts of Ellenville, situated at the base of the rolling Catskills within the Shawangunk valley. There is a pellet stove that will be lit on chilly nights, upon request. During the summer months, there is air conditioning available making a cool and cozy retreat from the heat of the summer. There are two additional cottages on the property.
4.94 out of 5 average rating, 179 reviews
Modern Upstate Escape with Outdoor Sauna
Recently 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.
4.94 out of 5 average rating, 416 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.
4.92 out of 5 average rating, 386 reviewsPopular amenities for cottage rentals in Middletown
Cottage rentals with a hot tub

Ye Little Wood | Cozy Forest Cottage with Hot Tub
5.0 out of 5 average rating, 253 reviews
Hot Tub, Playground, 3 Acres, and Much More!
4.97 out of 5 average rating, 310 reviews
Secluded Lakeview Escape with Hot Tub
4.98 out of 5 average rating, 155 reviews
Lovely Cottage w/ Jacuzzi+Access to Nearby Lakes!
4.91 out of 5 average rating, 175 reviews
Peaceful Lakeside Retreat-Easy Drive from NYC & NJ
4.99 out of 5 average rating, 194 reviews
Catskills Woodstock Design Retreat w/ hot tub
4.97 out of 5 average rating, 140 reviews
Catskills Cottage w/ Hot Tub & View
4.95 out of 5 average rating, 147 reviews
Catskills Memories · Hot Tub·Sauna·Fire Pit·Vinyl
4.98 out of 5 average rating, 109 reviewsPet-friendly cottage rentals

100 Private Acres in a Mid-century home
4.82 out of 5 average rating, 105 reviews
Hudson Valley Lakefront Cottage | Nature Escape
4.96 out of 5 average rating, 121 reviews
Ridgetop 2 Br Cabin- Views, 130acre forest & falls
4.93 out of 5 average rating, 363 reviews
Catskills Country Cottage
4.96 out of 5 average rating, 173 reviews
Private Lake House 1 Hour to NYC & Near Westpoint
4.96 out of 5 average rating, 252 reviews
The Carriage House
4.98 out of 5 average rating, 140 reviews
Be in Nature at this Gorgeous Riverfront Cabin
4.91 out of 5 average rating, 398 reviews
Peaceful Cottage-in Private 5-acre field
4.99 out of 5 average rating, 131 reviewsPrivate cottage rentals

Old Mill Cottage - Upstate Mountain Views
4.97 out of 5 average rating, 406 reviews
Cozy Cottage | Sauna + Stone Patio w/ Firepit
4.82 out of 5 average rating, 1025 reviews
Lake house
4.88 out of 5 average rating, 384 reviews
Lakefront Getaway : Mountain & Lake views
4.95 out of 5 average rating, 347 reviews
Heron's Hideaway: Stylish Lakefront 5 BR Home
4.96 out of 5 average rating, 123 reviews
Historic cottage near Mohonk & Minnewaska, 2BR/2BA
4.92 out of 5 average rating, 119 reviews
Modern Country Cottage by Bear Mountain
4.97 out of 5 average rating, 229 reviews
The Cottage
4.99 out of 5 average rating, 249 reviewsDestinations to explore
- New York Holiday rentals
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- Mountain Creek Resort
- American Dream
- Yankee Stadium
- MetLife Stadium
- Bushkill Falls
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bethel Woods Center for the Arts
- Delaware Water Gap National Recreation Area
- Nickelodeon Universe
- Resorts World Catskills
- Promised Land State Park
- Storm King Art Center
- Mohonk Preserve
- Mountain Creek Water Park
- Peekamoose Blue Hole
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mount Peter Ski Area
- Shawnee Mountain Ski Area
- SoJo Spa Club
- Wawayanda State Park





