
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!

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.

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.

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.

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.

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

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.

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!

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!

100 Private Acres in a Mid-century home
Discover serenity in our newly renovated mid-century ranch house nestled on 100+ acres of forever wild land, where modern comfort meets 1950s charm. Whether savoring wine, engaging in board games, or relishing classic vinyl records, every moment is enveloped in tranquility. Wake up to breathtaking views of the Shawangunk and surrounding forest from the expansive back deck. Perfect for morning coffee. Get lost exploring the secluded beauty that surrounds this picturesque retreat.

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.

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.
Popular amenities for cottage rentals in Middletown
Cottage rentals with a hot tub

Catskills Cottage (w/ Hot Tub) on Top of the World

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

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Secluded Lakeview Escape with Hot Tub

Lovely Cottage w/ Jacuzzi+Access to Nearby Lakes!

Peaceful Lakeside Retreat-Easy Drive from NYC & NJ

Catskills Woodstock Design Retreat w/ hot tub

Catskills Cottage w/ Hot Tub & View
Pet-friendly cottage rentals

Cozy Lake Cottage

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

Hudson Valley Lakefront Cottage | Nature Escape

Historic Gem in Culver Lake. (Branchville NJ)

Private Lake House 1 Hour to NYC & Near Westpoint

Beautiful stream side cottage in the woods

Catskills Country Cottage

Cozy Lakeview Catskills Cottage Near Hiking&Skiing
Private cottage rentals

Old Mill Cottage - Upstate Mountain Views

Cozy Cottage | Sauna + Stone Patio w/ Firepit

Lake house

Lakefront Getaway : Mountain & Lake views

Historic cottage near Mohonk & Minnewaska, 2BR/2BA

Stardust Cottage—Rustic retreat in Catskills Hamlet

Bella Cottage w/Pool, BBQ - Catskill Getaway

Cheerful Private 3 Bedroom Cottage in Cold Spring
Destinations to explore
- New York Holiday rentals
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- Mountain Creek Resort
- Yankee Stadium
- American Dream
- 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
- Peekamoose Blue Hole
- Mountain Creek Water Park
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mount Peter Ski Area
- SoJo Spa Club
- Wawayanda State Park
- Shawnee Mountain Ski Area





