Home Vacation Rentals By Owner In Middletown, NY

Showing 20 Of 31 Vacation Rentals
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Exceptional(2)

$207.46

/ Nightly
Caravan Park/Campsite

Waterlily-Best glamping experience, Middletown ny

Middletown, New York, United States

Beautiful glamping experience. All twin size beds come with a fitted sheet, one pillow and pillowcase. All queen size beds come with a fitted sheet, two pillows with pillowcases. Blankets available for $15.00 each bed. brQuiet private setting in beautiful forest, minutes from Middletown for major shopping areas & dining. Close to numerous attractions including Legoland & local wineries. Gas grill w/ side burner (gas included), firepit, picnic table, Fan w/lights, bluetooth LED alarm, lighting, private outdoor seating w/umbrella & hammocks, multiple usb ports, mini-fridge.brbrADDITIONAL FEE APPLIES FOR RESERVATIONS SPLITTING A WEEKEND.brbrbrThere are shared portable bathrooms approximately 75 feet from your site and there are also shared flushing toilets and showers a short walk away one to two minutes.brbrbrNo dangerous animals to include any dog from the bull family or any animal that displays aggression. All animals must be kept on a leash and supervised at all times. Pet fee is $60 for the first pet, $50 for each additional pet. brbrParking: Your first vehicle is free. Each additional space is $15 per night. brbrSmoking allowed in designated areas only. Each site has a private smoking area.brbrNo candles, heaters or other heat sources or open flames inside or immediately near tent.br*Fire wood is available for $9/bundle (good for small 1.5-2h fire) or $50/bucket (good for 2 day+ stay) – to be used in designated fire pit only. Fire starters available for $4.brNo outside fire wood permitted. Please help us keep our forest safe from outside critters. brbrbrGuests have free access to a shared, open pool.brPool open based on weather. Certain blackout hours or dates may apply.brbr*Access to hot tub and sauna is $39/2 hour block. Please message us to inquire about availability.brbrOur glamping tents are located on the grounds of Ring Homestead Adventure Camp. There are numerous exciting activities you can try while here: zip line, ropes course, paintball, year round snow tubing & many others, for discounted rate.brbrCatch & release fishing available at no charge. Bring your own rod.brbrAt certain times during the day you’ll most likely hear the laugh and loud expressions of excitement from our groups of kids or adults who come for day activities.br
Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps

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$130.66

/ Nightly
Caravan Park/Campsite

Victor-amazing glamping experience-Middletown NY

Middletown, New York, United States

Beautiful glamping experience. All twin size beds come with a fitted sheet, one pillow and pillowcase. All queen size beds come with a fitted sheet, two pillows with pillowcases. Blankets available for $15.00 each bed. brQuiet private setting in beautiful forest, minutes from Middletown for major shopping areas & dining. Close to numerous attractions including Legoland & local wineries. Gas grill w/ side burner (gas included), firepit, picnic table, Fan w/lights, bluetooth LED alarm, lighting, private outdoor seating w/umbrella & hammocks, multiple usb ports, mini-fridge.brbrADDITIONAL FEE APPLIES FOR RESERVATIONS SPLITTING A WEEKEND.brbrbrThere are shared portable bathrooms approximately 75 feet from your site and there are also shared flushing toilets and showers a short walk away one to two minutes.brbrbrNo dangerous animals to include any dog from the bull family or any animal that displays aggression. All animals must be kept on a leash and supervised at all times. Pet fee is $60 for the first pet, $50 for each additional pet. brbrParking: Your first vehicle is free. Each additional space is $15 per night. brbrSmoking allowed in designated areas only. Each site has a private smoking area.brbrNo candles, heaters or other heat sources or open flames inside or immediately near tent.br*Fire wood is available for $9/bundle (good for small 1.5-2h fire) or $50/bucket (good for 2 day+ stay) – to be used in designated fire pit only. Fire starters available for $4.brNo outside fire wood permitted. Please help us keep our forest safe from outside critters. brbrbrGuests have free access to a shared, open pool.brPool open based on weather. Certain blackout hours or dates may apply.brbr*Access to hot tub and sauna is $39/2 hour block. Please message us to inquire about availability.brbrOur glamping tents are located on the grounds of Ring Homestead Adventure Camp. There are numerous exciting activities you can try while here: zip line, ropes course, paintball, year round snow tubing & many others, for discounted rate.brbrCatch & release fishing available at no charge. Bring your own rod.brbrAt certain times during the day you’ll most likely hear the laugh and loud expressions of excitement from our groups of kids or adults who come for day activities.br
Bed 1

Bed

Bath 1

Bath

Sleep 5

Sleeps

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$155.23

/ Nightly
Caravan Park/Campsite

Sunshine- -Best glamping experience, Middletown ny

Middletown, New York, United States

Beautiful glamping experience. All twin size beds come with a fitted sheet, one pillow and pillowcase. All queen size beds come with a fitted sheet, two pillows with pillowcases. Blankets available for $15.00 each bed. brQuiet private setting in beautiful forest, minutes from Middletown for major shopping areas & dining. Close to numerous attractions including Legoland & local wineries. Gas grill w/ side burner (gas included), firepit, picnic table, Fan w/lights, bluetooth LED alarm, lighting, private outdoor seating w/umbrella & hammocks, multiple usb ports, mini-fridge.brbrADDITIONAL FEE APPLIES FOR RESERVATIONS SPLITTING A WEEKEND.brbrbrThere are shared portable bathrooms approximately 75 feet from your site and there are also shared flushing toilets and showers a short walk away one to two minutes.brbrbrNo dangerous animals to include any dog from the bull family or any animal that displays aggression. All animals must be kept on a leash and supervised at all times. Pet fee is $60 for the first pet, $50 for each additional pet. brbrParking: Your first vehicle is free. Each additional space is $15 per night. brbrSmoking allowed in designated areas only. Each site has a private smoking area.brbrNo candles, heaters or other heat sources or open flames inside or immediately near tent.br*Fire wood is available for $9/bundle (good for small 1.5-2h fire) or $50/bucket (good for 2 day+ stay) – to be used in designated fire pit only. Fire starters available for $4.brNo outside fire wood permitted. Please help us keep our forest safe from outside critters. brbrbrGuests have free access to a shared, open pool.brPool open based on weather. Certain blackout hours or dates may apply.brbr*Access to hot tub and sauna is $39/2 hour block. Please message us to inquire about availability.brbrOur glamping tents are located on the grounds of Ring Homestead Adventure Camp. There are numerous exciting activities you can try while here: zip line, ropes course, paintball, year round snow tubing & many others, for discounted rate.brbrCatch & release fishing available at no charge. Bring your own rod.brbrAt certain times during the day you’ll most likely hear the laugh and loud expressions of excitement from our groups of kids or adults who come for day activities.br
Bed 1

Bed

Bath 1

Bath

Sleep 7

Sleeps

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Exceptional(4)

$209.05

/ Nightly
Caravan Park/Campsite

Route 66 - Glamping experience in Middletown NY

Middletown, New York, United States

Beautiful glamping experience. All twin size beds come with a fitted sheet, one pillow and pillowcase. All queen size beds come with a fitted sheet, two pillows with pillowcases. Blankets available for $15.00 each bed. brQuiet private setting in beautiful forest, minutes from Middletown for major shopping areas & dining. Close to numerous attractions including Legoland & local wineries. Gas grill w/ side burner (gas included), firepit, picnic table, Fan w/lights, bluetooth LED alarm, lighting, private outdoor seating w/umbrella & hammocks, multiple usb ports, mini-fridge.brbrADDITIONAL FEE APPLIES FOR RESERVATIONS SPLITTING A WEEKEND.brbrbrThere are shared portable bathrooms approximately 75 feet from your site and there are also shared flushing toilets and showers a short walk away one to two minutes.brbrbrNo dangerous animals to include any dog from the bull family or any animal that displays aggression. All animals must be kept on a leash and supervised at all times. Pet fee is $60 for the first pet, $50 for each additional pet. brbrParking: Your first vehicle is free. Each additional space is $15 per night. brbrSmoking allowed in designated areas only. Each site has a private smoking area.brbrNo candles, heaters or other heat sources or open flames inside or immediately near tent.br*Fire wood is available for $9/bundle (good for small 1.5-2h fire) or $50/bucket (good for 2 day+ stay) – to be used in designated fire pit only. Fire starters available for $4.brNo outside fire wood permitted. Please help us keep our forest safe from outside critters. brbrbrGuests have free access to a shared, open pool.brPool open based on weather. Certain blackout hours or dates may apply.brbr*Access to hot tub and sauna is $39/2 hour block. Please message us to inquire about availability.brbrOur glamping tents are located on the grounds of Ring Homestead Adventure Camp. There are numerous exciting activities you can try while here: zip line, ropes course, paintball, year round snow tubing & many others, for discounted rate.brbrCatch & release fishing available at no charge. Bring your own rod.brbrAt certain times during the day you’ll most likely hear the laugh and loud expressions of excitement from our groups of kids or adults who come for day activities.br
Bed 1

Bed

Bath 1

Bath

Sleep 12

Sleeps

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Exceptional(1)

$198.5

/ Nightly
Private Vacation Home

Woodsie - best glamping experience Middletown ny

Middletown, New York, United States

Beautiful glamping experience. All twin size beds come with a fitted sheet, one pillow and pillowcase. All queen size beds come with a fitted sheet, two pillows with pillowcases. Blankets available for $15.00 each bed. brQuiet private setting in beautiful forest, minutes from Middletown for major shopping areas & dining. Close to numerous attractions including Legoland & local wineries. Gas grill w/ side burner (gas included), firepit, picnic table, Fan w/lights, bluetooth LED alarm, lighting, private outdoor seating w/umbrella & hammocks, multiple usb ports, mini-fridge.brbrADDITIONAL FEE APPLIES FOR RESERVATIONS SPLITTING A WEEKEND.brbrbrThere are shared portable bathrooms approximately 75 feet from your site and there are also shared flushing toilets and showers a short walk away one to two minutes.brbrbrNo dangerous animals to include any dog from the bull family or any animal that displays aggression. All animals must be kept on a leash and supervised at all times. Pet fee is $60 for the first pet, $50 for each additional pet. brbrParking: Your first vehicle is free. Each additional space is $15 per night. brbrSmoking allowed in designated areas only. Each site has a private smoking area.brbrNo candles, heaters or other heat sources or open flames inside or immediately near tent.br*Fire wood is available for $9/bundle (good for small 1.5-2h fire) or $50/bucket (good for 2 day+ stay) – to be used in designated fire pit only. Fire starters available for $4.brNo outside fire wood permitted. Please help us keep our forest safe from outside critters. brbrbrGuests have free access to a shared, open pool.brPool open based on weather. Certain blackout hours or dates may apply.brbr*Access to hot tub and sauna is $39/2 hour block. Please message us to inquire about availability.brbrOur glamping tents are located on the grounds of Ring Homestead Adventure Camp. There are numerous exciting activities you can try while here: zip line, ropes course, paintball, year round snow tubing & many others, for discounted rate.brbrCatch & release fishing available at no charge. Bring your own rod.brbrAt certain times during the day you’ll most likely hear the laugh and loud expressions of excitement from our groups of kids or adults who come for day activities.br
Bed 1

Bed

Bath 1

Bath

Sleep 5

Sleeps

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Exceptional(7)

$174.41

/ Nightly
Caravan Park/Campsite

Orion - Beautiful Middletown Glamping experience

Middletown, New York, United States

Beautiful glamping experience. All twin size beds come with a fitted sheet, one pillow and pillowcase. All queen size beds come with a fitted sheet, two pillows with pillowcases. Blankets available for $15.00 each bed. brQuiet private setting in beautiful forest, minutes from Middletown for major shopping areas & dining. Close to numerous attractions including Legoland & local wineries. Gas grill w/ side burner (gas included), firepit, picnic table, Fan w/lights, bluetooth LED alarm, lighting, private outdoor seating w/umbrella & hammocks, multiple usb ports, mini-fridge.brbrADDITIONAL FEE APPLIES FOR RESERVATIONS SPLITTING A WEEKEND.brbrbrThere are shared portable bathrooms approximately 75 feet from your site and there are also shared flushing toilets and showers a short walk away one to two minutes.brbrbrNo dangerous animals to include any dog from the bull family or any animal that displays aggression. All animals must be kept on a leash and supervised at all times. Pet fee is $60 for the first pet, $50 for each additional pet. brbrParking: Your first vehicle is free. Each additional space is $15 per night. brbrSmoking allowed in designated areas only. Each site has a private smoking area.brbrNo candles, heaters or other heat sources or open flames inside or immediately near tent.br*Fire wood is available for $9/bundle (good for small 1.5-2h fire) or $50/bucket (good for 2 day+ stay) – to be used in designated fire pit only. Fire starters available for $4.brNo outside fire wood permitted. Please help us keep our forest safe from outside critters. brbrbrGuests have free access to a shared, open pool.brPool open based on weather. Certain blackout hours or dates may apply.brbr*Access to hot tub and sauna is $39/2 hour block. Please message us to inquire about availability.brbrOur glamping tents are located on the grounds of Ring Homestead Adventure Camp. There are numerous exciting activities you can try while here: zip line, ropes course, paintball, year round snow tubing & many others, for discounted rate.brbrCatch & release fishing available at no charge. Bring your own rod.brbrAt certain times during the day you’ll most likely hear the laugh and loud expressions of excitement from our groups of kids or adults who come for day activities.br
Bed 1

Bed

Bath 1

Bath

Sleep 12

Sleeps

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Exceptional(32)

$663.75

/ Nightly
Private Vacation Home

Wawayanda House on 62 Acres - Multiple Fireplaces!

Middletown, New York, United States

Escape the hustle and bustle of city life and stay at this secluded Wawayanda vacation rental home! Nestled on 62 private acres, surrounded by lush woods and streams, this property offers plenty of peace and quiet and will serve as a tranquil setting for your next retreat to New York's beautiful Hudson Valley area. The expansive 5-bedroom, 3-bath vacation rental offers easy access to hiking, skiing at Holiday Mountain, numerous vineyards, West Point, and the historic Vanderbilt Mansion!brbr-- THE PROPERTY --brbr3,800 Sq Ft | 2 Charcoal Grills | On-Site Hiking | DeckbrbrSerene forested views, not to mention the old cabins defining the property’s unique character, and a spacious interior filled with the comforts of home, make this sprawling residence a terrific destination for families or a group of friends out for a rejuvenating getaway.brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: 2 Twin BedsbrbrPROPERTY: Outdoor seating, brook, pond, 1,200-foot driveway, walking trailsbrINDOOR LIVING: flat-screen cable TV, 3 fireplaces, exposed beams, cathedral ceilings, hardwood floors, study, pianobrKITCHEN: Fully equipped, double oven, 2-person breakfast bar, dining table, Keurig, drip coffee maker, cooking basics, dishware & flatwarebrGENERAL: Free WiFi, A/C window units, central heating, linens/towels, washer/dryer (available for long stays), cleaning essentialsbrFAQ: Step-free access, exterior security camera (facing out)brPARKING: Open parking (2 vehicles), no quads or 4x4 vehiclesbrbr-- THE LOCATION --brbrOUTDOOR ADVENTURE: Highland Lakes State Park (16.7 miles), Shawangunk Ridge State Forest (28.4 miles), Neversink Gorge Trail (28.6 miles), Mountain Wings (28.7 miles), Ellenville Flight Park (28.7 miles), Bear Hill Preserve (29.8 miles), Minnewaska State Park Preserve (30.7 miles), Ice Caves (30.8 miles), Verkeerderkill Falls (30.8 miles), Peekamoose Blue Hole (51.7 miles)brSKI RESORTS: Holiday Mountain Ski & Fun (26.8 miles), Ski Big Bear at Masthope Mountain (40.5 miles)brVINEYARDS: Christopher Jacobs Winery at Pennings Vineyards (24.4 miles), Baldwin Vineyards (25.8 miles), Whitecliff Vineyard & Winery (34.1 miles), Robibero Winery (35.5 miles)brTHINGS TO SEE & DO: The Castle Fun Center (15.6 miles), Cragsmoor Stone Church (30.1 miles), Pine Ridge Dude Ranch (39.4 miles), Historic Site of the 1969 Woodstock Festival (42.4 miles), Vanderbilt Mansion National Historic Site (53.9 miles)brNEARBY TOWNS: Slate Hill (3.0 miles), Minisink (5.3 miles), Goshen (12.0 miles), Milford, PA (16.7 miles), Warwick (17.4 miles), Monticello (31.2 miles), West Point (37.1 miles)brAIRPORT: Stewart International Airport (27.5 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- Must be at least 25 years old to book br- No huntingbr- No fireworksbr- No guns or firearmsbr- No excessive noise br- Please respect the neighborsbr- Only people on reservation allowed at property unless previously approved by homeownerbr- No events, parties, or large gatheringsbr- Additional fines may be imposed if these policies are violatedbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Your safety matters. This property features an exterior camera. The camera does not look into any interior spaces
Bed 5

Bed

Bath 3

Bath

Sleep 8

Sleeps

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Exceptional(4)

$439.25

/ Nightly
Cabin

Inkwell Gardens: A Modern Cabin in Middletown Close to Legoland, Golf, Hiking+

Middletown, New York, United States

One of the first things you notice when arriving at Inkwell Gardens are the many outdoor spaces available to relax and enjoy the surroundings. We have three decks which can be a great spot to hangout with friends and family or a welcomed retreat for peace and quiet. Walk the front and back lawn to stretch out and maybe spot a woodpecker or two. We have a generous sized fire pit for enjoying s’mores and the sounds of crackling wood. A hammock hangs in the backyard, perfect for an afternoon nap. No matter where you find yourself outside, you’ll be greeted by the many hummingbirds that also make our space their home.brbrWalking in the front door leads you to the open dining and living area. Here you'll find a diverse collection of records to spin or you gather around for dinner and a movie on our Smart TV. Behind the dining area is a fully stocked kitchen with breakfast nook overlooking the garden walkway. The coffee bar is supplied with a drip machine, moka pot and a Fellow Stagg electric gooseneck kettle. Leaving the kitchen, the foyer leads you past the first floor half bathroom and into our creative office space lined with thriving plants and sun drenched afternoons. The back door leads you outside and onto the deck, where you can fire up the grill or sit back and stargaze. Stairs leading up from the living room, bring you to the second floor landing. From here, all three bedrooms and the upstairs bathroom can be accessed.brbrThe bathroom is equipped with a deep soaking tub and dual shower heads, great for relaxing after an eventful day.brbrThe first guest room, the “Blue Room”, has a queen sized bed, closet, and a small chest of drawers. Kick back and enjoy the works on the gallery wall or sit on the comfy chair, grab a book and start a journey through the classics.brbrThe second guest room, the “Red Room”, has a queen sized bed and a closet. A collection of eclectic pieces inspired by nature and books for Children through Young Adult readers can be enjoyed.brbrThe large master bedroom, the “Green Room”, has a king sized bed, a chest of drawers, a vanity, and a closet. Grab a book from the collection, walk out onto the private balcony and enjoy reading while listening to the sounds of nature.brbrbrbrA sneak peek at some amenities:brbrLegoland - 15 minutesbrThree breweries in town all 10 minutes awaybrMultiple hiking trails less than 10 minutes awaybrFarm offerings - 5 minutesbrDrive in movie theater - 5 minutesbrGalleria Mall and Round One arcade - 10 minutesbrWoodbury Common Luxury Outlets - 25 minutesbrbrThere are many more recommendations waiting for you at the cabin, but if you have any questions regarding other amenities or events - feel free to ask!
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(1)

$134.42

/ Nightly
Caravan Park/Campsite

Bliss - beautiful Glamping experience in Middletown, NY

Middletown, New York, United States

Beautiful glamping experience. All twin size beds come with a fitted sheet, one pillow and pillowcase. All queen size beds come with a fitted sheet, two pillows with pillowcases. Blankets available for $15.00 each bed. brQuiet private setting in beautiful forest, minutes from Middletown for major shopping areas & dining. Close to numerous attractions including Legoland & local wineries. Gas grill w/ side burner (gas included), firepit, picnic table, Fan w/lights, bluetooth LED alarm, lighting, private outdoor seating w/umbrella & hammocks, multiple usb ports, mini-fridge.brbrADDITIONAL FEE APPLIES FOR RESERVATIONS SPLITTING A WEEKEND.brbrbrThere are shared portable bathrooms approximately 75 feet from your site and there are also shared flushing toilets and showers a short walk away one to two minutes.brbrbrNo dangerous animals to include any dog from the bull family or any animal that displays aggression. All animals must be kept on a leash and supervised at all times. Pet fee is $60 for the first pet, $50 for each additional pet. brbrParking: Your first vehicle is free. Each additional space is $15 per night. brbrSmoking allowed in designated areas only. Each site has a private smoking area.brbrNo candles, heaters or other heat sources or open flames inside or immediately near tent.br*Fire wood is available for $9/bundle (good for small 1.5-2h fire) or $50/bucket (good for 2 day+ stay) – to be used in designated fire pit only. Fire starters available for $4.brNo outside fire wood permitted. Please help us keep our forest safe from outside critters. brbrbrGuests have free access to a shared, open pool.brPool open based on weather. Certain blackout hours or dates may apply.brbr*Access to hot tub and sauna is $39/2 hour block. Please message us to inquire about availability.brbrOur glamping tents are located on the grounds of Ring Homestead Adventure Camp. There are numerous exciting activities you can try while here: zip line, ropes course, paintball, year round snow tubing & many others, for discounted rate.brbrCatch & release fishing available at no charge. Bring your own rod.brbrAt certain times during the day you’ll most likely hear the laugh and loud expressions of excitement from our groups of kids or adults who come for day activities.br
Bed 1

Bed

Bath 2

Bath

Sleep 5

Sleeps

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Exceptional(2)

$366.05

/ Nightly
Cottage

CHARMING BOHO-STYLE COTTAGE IN MIDDLETOWN NY

Middletown, New York, United States

EXPERIENCE SOMETHING DIFFERENT. GO BACK IN TIME WHILE LIVING IT UP IN THE PRESENT.brbrLocated in bustling Middletown NY, this cozy cottage, sitting on a private property that calls for you to come outside, has been renovated for modern vacationers while keeping intact its natural and bohemian rural allure. The home sits just across the street from the popular Korn’s campgroundbrSet up shop inside this inviting rustic cabin sleeping 8, and enjoy your stay appreciating the mountain air surrounding you. An enclosed sunroom with lots of cushioned seating invites sunlight into your stay, while a gated deck with a patio set surrounds the house to provide you with ample space for life outside.brbr•Home has been renovated (2022) with brand new bathrooms and other areas redone to accommodate city dwellers.brbrA vintage and antique fireplace in great condition connects the different levels of the home for when the weather gets chilly. Powerful AC units have been installed for those hot summer days, and new smart flatscreens are available for your enjoyment when you wish to indulge in the offerings of the modern world.brbr•On the main floor you will find a cozy kitchen stocked with everything you may need during your stay, including a coffee maker, appliances, dishes, utensils and more. Nearby is a dining table for nourishing bodies and relationships. The living space offers a high-ceiling log cabin environment with inviting chairs and lounging.brbr•Outdoors on this property you will find yourself enjoying the best of nature and leisure. An above ground pool along with a newly built deck and nighttime lighting makes every summer day - and night -  a delight. A large wooded area to get in touch with nature is yours to enjoy.brbr•Sleeping arrangements and accommodations:brbr-Main floor offers one inviting bedroom with a queen-size bed, a designated work space, and ample room to hang up clothing.brbr-Upstairs you will find one large bedroom with a king-size bed, an ottoman, a spacious closet and a strong split-unit AC, along with a remodeled bathroom that includes a sitting shower.brbr-The basement offers a bedroom with two full-size beds and memory foam mattresses, as well as a couch that can be opened to serve as another bed. A washer  and dryer are also available downstairs for your convenience.
Bed 4

Bed

Bath 2

Bath

Sleep 9

Sleeps

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