
House holiday rentals in Middletown
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Top-rated house rentals in Middletown
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Highland Lakes View, Big Home - Family Fun, Vernon
Lakefront VIEWS!— NO lake access at house. Large, family-friendly home in quiet Highland Lakes. Community club access (summer): 5 lakes, beaches, clubhouse & boat launches — $2 pp/day. Walk to club dock only two houses away! ⭐ 75+ five-star reviews ☕ Coffee & breakfast snacks 🎲 Board games & arcade 🗽 1 HR from NYC 5 min Wawayanda State Park 10 min Mountain Creek, App Trail, Great Gorge, Minerals, Vernon 15 min Warwick, wineries, Crystal Springs 25 min Mt Peter 35 min LEGOLAND NY & JH-WF HQ
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Entire Home (private pool), Event Friendly
This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Beaver Lake Escape
Welcome to Beaver Lake Escape! This one bedroom, one bathroom lakeview home has all of the amenities you will need for a relaxing vacation getaway! Come experience a warm & cozy environment with full access to the community beach where you can enjoy kayaking, swimming and fishing (catch & release). You'll also find great hiking in the Spring, Summer and Fall at the Neversink Gorge Unique Area and skiing/snow boarding in the winter at Holiday Mountain! Only a 25 minute drive to Bethel Woods!

TheGoshenGetawayPoolHotTubLegoLandArcade
TheGG is a beautiful spacious home with more amenities than one can ask for! Cooking for 10? We have options! Our double oven is perfect for holiday dinners! Not to mention our customs built outdoor kitchen and grill! Keep your kids entertained by throwing a pizza party using our beautiful stainless pizza oven! Burn those calories off in a private gym or laps in the heated pool MAY1ST Then relax in our 8per hot tub! Bring your clubs! Near by are four 18hole golf course with in a 15min drive!

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Victorian At Orange Square Entire Home
Immediately Feel Welcome As You Walk On To The Pillared Front Porch With Its Cushioned Deck Furniture. Enter The Welcoming Foyer And Feel The Comfort Of Home. Sink Deep In The Stuffed Couches In Front Of The Remote Controlled Gas Fireplace. Enjoy Your Favorite Book Or The Smart TV Entertainment Center. If Inclined Cook A Meal In The Modern Kitchen And Dine In The Elegant Dining Room With A Wood Burning Fireplace. Fire pit in back yard that can be viewed from the 6 person 104 degree Jacuzzi.

Hillside Views in Hudson Valley
Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Peace and quiet. Comfy, private house to relax in
Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

Spectacular Lake Views from Every Room & Garden
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Cozy Rustic Farmhouse With Wood Stove
Make yourself at home in this unique farmhouse just an hour and a half away from NYC! Located right on the Bashakill Wildlife Refuge. this is the perfect getaway near Neversink Unique Area, Minnewaska State Park, Sam's Point, Legoland, and more! Enjoy the flicker of a wood-burning stove, make a BBQ feast on the outdoor deck, or admire the stars on a clear, dark night while sitting around the campfire. Good for couples, friends, or families–just no pets, please!

Cozy farmhouse & stunning views on 135 acres
A gorgeous, spacious and secluded retreat with a fabulous swimming/skating pond and two wood-burning stoves surrounded by 135 acres of meadow and hiking trails, and a short jaunt to miles of untouched wilderness. This 160-year-old farmhouse is super cozy in winter and can easily accommodate large groups but offers plenty of privacy. The place has it all but don't take our word for it - read the reviews and check out the pictures!
Popular amenities for house rentals in Middletown
House rentals with a pool

Entertainers Retreat • Fire Pit + Games • Hot Tub

4Br Mountain Brook House on 130 acres w/ trails

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings

6-Acre Narrowsburg Estate: Private Pool, Hot-Tub

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Spacious Catskills Farmhouse on over 5 acres!
Fenced & Salt Water Pool | Cozy Catskills Cottage

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
Weekly house rentals

The Wooden Igloo Near Legoland NY

The Alexandria - Wurstboro, NY

Fairway Retreat - Montgomery, NY

Hudson Valley Home with Pool & Jacuzzi

Accord River House

Serene Hudson Valley Escape Hottub/Pool/King Suite

Casa Bashakill

Serene Home in the Catskills Woods
Private house rentals

The Hilltop • Fenced 8-Acre Dog-Friendly Retreat

Lake House

Mohonk Abode | dog friendly + near hiking

Cabin96-Shawangunk Mountain View

Luxury Mountain Retreat with Panoramic Vista Views

Lunar Lounge • 6 acres • Fireplace • Pet Friendly

World Cup Base ~ Lakefront House w/ Hot Tub & View

Catskill Mountains Forest Nest for 2
Quick stats about house rentals in Middletown

Total holiday rentals
Explore 10 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at £29 per night before taxes and fees

Verified guest reviews
Over 50 verified reviews to help you choose

Wifi availability
10 of Middletown holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Middletown rentals

4.6 Average rating
Middletown stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Bushkill Falls
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- American Dream
- Delaware Water Gap National Recreation Area
- Resorts World Catskills
- Nickelodeon Universe
- Brotherhood, America's Oldest Winery
- Mount Peter Ski Area
- Promised Land State Park
- Riverside Park
- Bear Mountain State Park
- Campgaw Mountain Ski Area
- Shawnee Mountain Ski Area
- Wawayanda State Park
- SoJo Spa Club
- Storm King Art Center
- Paterson Great Falls National Historical Park
- St. Nicholas Park





