$0
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Home in Chester, New York

Spacious Retreat w/ Pool, Hot Tub & Great Room

7 bedrooms

12 beds

4 bathrooms

16 guests

1000 sq. ft.

Operated by a Wander partner

Trusted operators, vetted by Wander

About the property

Escape to this spacious 7BR Monroe retreat designed for unforgettable group getaways. Relax in the heated pool, unwind in the year-round hot tub, gather around the fire pit, or enjoy the stunning 20-ft great room with soaring ceilings and a 72” Fire TV. Sleeping 18+ guests, this home is perfect for families, retreats, reunions, and celebrations near hiking, shopping, and Hudson Valley attractions. Hosted by Stayshores.

This large Monroe home gives families and groups the space to gather, relax, and enjoy a peaceful stay in the Hudson Valley. It's a comfortable family home with strong outdoor amenities, not a luxury resort or event venue, so please review the layout, bedroom count, bathroom count, and amenity details carefully before booking to confirm it's the right fit for your group.

🛏️ Sleeping Arrangements

The home sleeps up to 21 guests across 7 bedrooms and 12 beds, with 4 bathrooms shared throughout the home.

Bedroom 1: 2 queen beds — sleeps up to 4
Bedroom 2: 2 queen beds — sleeps up to 4
Bedroom 3: 2 queen beds — sleeps up to 4
Bedroom 4: 2 queen beds — sleeps up to 4
Bedroom 5: 2 twin beds — sleeps up to 2
Bedroom 6: 1 twin bed — sleeps 1
Bedroom 7: 1 queen bed — sleeps up to 2

Total: 9 queen beds + 3 twin beds = 12 beds

For larger groups, we recommend reviewing the bedroom and bathroom configuration before booking to make sure the arrangement works comfortably for everyone.

🛋️ Great Room & Indoor Living

The great room is the main indoor gathering space and one of the standout features of the home. Tall ceilings and natural light create an open setting where everyone can spend time together.

The home also offers:

• Comfortable group seating
• Multiple dining and gathering areas
• WiFi
• Dedicated workspace
• Space to relax between Hudson Valley adventures

🍳 Kitchen & Dining

The full kitchen is equipped for preparing family meals, quick breakfasts, and longer stays.

Amenities include:

• Refrigerator
• Stove and oven
• Microwave
• Cookware
• Dinnerware and utensils
• Food-preparation space
• Indoor and outdoor dining areas

Having a full kitchen can be especially convenient for larger groups who prefer to enjoy some meals together at the house.

🌳 Outdoor Space

The outdoor amenities are one of the highlights of the property, with plenty of ways for families and groups to enjoy time outside.

• Seasonal heated pool
• Seasonal hot tub
• Fire pit
• Gazebo
• Large lawn
• Trampoline
• Swing set
• Outdoor seating and dining areas

Whether you're enjoying a summer afternoon by the pool or gathering outside after a day of exploring, the yard gives the group additional room to spread out.

💦 Heated Pool & Hot Tub

The heated outdoor pool is generally available from Memorial Day through Labor Day, weather and maintenance permitting.

Pool heating is included at no additional charge.

During pool season, guests have 24-hour access to the pool. Please be considerate of neighborhood quiet hours when enjoying outdoor amenities during late-night or early-morning hours.

The hot tub is generally available from March through October, weather and maintenance permitting.

Water temperatures may vary depending on weather and equipment conditions. Routine pool and hot tub service may occasionally take place during a reservation to keep these amenities clean and guest-ready.

👨‍👩‍👧‍👦 Family-Friendly Features

The home is particularly well suited for families and multi-generational groups who want to stay together.

In addition to the multiple bedrooms and spacious indoor gathering areas, families can enjoy the pool, hot tub, large lawn, trampoline, swing set, gazebo, fire pit, and outdoor seating.

Children must be appropriately supervised around the pool, hot tub, trampoline, swing set, fire pit, stairs, and other recreational areas.

💻 Work & Longer Stays

For guests combining vacation with work or planning a longer Hudson Valley stay, the home offers WiFi, a dedicated workspace, a full kitchen, multiple bedrooms, 4 bathrooms, and convenient on-site parking.

📍 Nearby Attractions & Points of Interest

The home is located in Monroe, New York, providing convenient access to shopping, family attractions, outdoor recreation, and Hudson Valley day trips.

Nearby destinations include:

• LEGOLAND New York Resort
• Woodbury Common Premium Outlets
• Harriman State Park
• Bear Mountain State Park
• West Point
• Hudson Valley wineries and breweries
• Hiking, parks, and scenic drives
• Local restaurants and shopping
• Day trips toward New York City

Drive times can vary depending on traffic, weather, and time of day.

Great For

• Family vacations
• Multi-family stays
• Multi-generational trips
• LEGOLAND getaways
• Woodbury Common shopping trips
• West Point visits
• Hudson Valley weekends
• Extended family stays
• Weekend escapes from NYC

The home is intended for peaceful residential stays and is not suitable for parties, events, or disruptive gatherings.

Guest Access

Guests have access to the designated guest areas of the home and property, including:

• 7 bedrooms and 4 bathrooms
• Living areas and great room
• Full kitchen and dining areas
• Workspace
• Seasonal heated pool
• Seasonal hot tub
• Fire pit
• Gazebo and lawn
• Trampoline and swing set
• Outdoor seating and dining areas
• Free on-site parking for up to 6 vehicles

Please park only in designated areas.

Some owner closets, supply areas, storage spaces, utility rooms, or maintenance areas may remain locked and are not available for guest use.

Guests have access to the home and outdoor amenities included with the reservation.

This includes:

7 bedrooms
4 bathrooms
Living areas
20-foot great room
Kitchen
Dining areas
Workspace
Seasonal pool
Hot tub
Fire pit
Gazebo
Lawn
Trampoline
Swing set
Outdoor seating
Parking area

Some owner closets, supply areas, storage rooms, utility spaces, or maintenance areas may be locked and are not available for guest use.

Guest Interaction

We give guests privacy during their stay, but we are available through Airbnb messages whenever needed.

This is a self-managed stay experience with check-in details provided before arrival. If you have questions before or during your stay, we are happy to help with the home, amenities, local recommendations, or anything else related to your reservation.

Scheduled service providers such as pool care, hot tub service, landscaping, pest control, trash service, or maintenance may access outdoor areas during the stay when needed to keep the property clean, safe, and guest-ready.

Location

The home is located in Monroe, New York, a convenient Hudson Valley area with access to family attractions, shopping, parks, outdoor activities, and day trips toward NYC.

Nearby highlights include:

Woodbury Common Premium Outlets
LEGOLAND New York
Harriman State Park
Bear Mountain State Park
West Point
Hudson Valley wineries and breweries
Local restaurants and shopping
Hiking, parks, and scenic drives
Convenient routes toward NYC and surrounding areas

Drive times may vary depending on traffic, weather, and time of day.

Perfect For

This home is a great fit for:

Family trips
Multi-family stays
Hudson Valley getaways
LEGOLAND visits
Woodbury Common shopping trips
West Point visits
Weekend escapes from NYC
Extended family stays
Respectful groups needing multiple bedrooms
Guests who want a large home with outdoor amenities

This home is not suitable for parties, disruptive gatherings, or unauthorized events.

We give guests privacy during their stay, but we are available through Airbnb messages whenever needed.

This is a self check-in property, and guests will receive check-in details before arrival. If you have any questions before or during your stay, we are happy to help with anything related to the home, amenities, local recommendations, or your reservation.

Our goal is to make your stay smooth, comfortable, and easy from check-in to checkout.

Scheduled service providers such as pool care, hot tub service, landscaping, pest control, trash service, or maintenance may access outdoor areas during the stay when needed to keep the property clean, safe, and guest-ready.

This is a spacious family home with 7 bedrooms, 11 beds, and 4 bathrooms. For larger groups, please review the bedroom and bathroom count carefully to make sure the layout works for your group.

The pool is seasonal and generally available from June through September, weather and maintenance permitting.

The hot tub is available year-round, but availability may be limited during extreme cold, severe weather, service needs, or maintenance.

Outdoor amenities such as the pool, hot tub, trampoline, swing set, fire pit, lawn, and gazebo may be affected by weather and seasonal conditions.

Children must be supervised at all times around the pool, hot tub, trampoline, swing set, fire pit, stairs, and outdoor spaces.

Only registered guests are allowed on the property unless approved in advance.

No parties, events, smoking, vaping, or unauthorized visitors are allowed.

Quiet hours and neighborhood rules must be respected.

House Rules

Please respect the home, neighbors, and property during your stay.

Check-in after 4:00 PM
Checkout before 11:00 AM
Maximum occupancy must match the reservation
No parties or events
No unauthorized guests or visitors
No smoking or vaping inside the home
No pets unless specifically approved in writing
Quiet hours must be respected
No amplified outdoor music
Children must be supervised around the pool, hot tub, trampoline, swing set, fire pit, stairs, and outdoor areas
Pool and hot tub use is at guests’ own risk
No glass near the pool or hot tub
Fire pit must be used safely and fully extinguished after use
Trampoline and swing set must be used responsibly and at guests’ own risk
Please do not move indoor furniture outside
Please keep doors and windows closed when not in use
Please report damage or maintenance issues right away
Parking is limited to approved areas only

Where you’ll sleep

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

BEDROOM

1 bed

Amenities

Common Amenities

  • Outdoor pool
  • Fire pit
  • Fire place
  • Patio
  • Garden view
  • High chair
  • Bed linens
  • Body soap
  • Carbon monoxide detector
  • Coffee maker
  • Conditioner
  • Cooking basics
  • Dishes
  • Dishwasher
  • Extra pillows
  • Fire extinguisher
  • First aid kit
  • Freezer
  • Garden
  • Hair dryer
  • Heating
  • Hot water
  • Iron
  • Kitchen
  • Microwave
  • Oven
  • Fridge
  • Shampoo
  • Smoke detector
  • Stove
  • Toaster
  • TV
  • Washer
  • Wifi
  • Air conditioning
  • Outdoor dining area
  • BBQ Utensils
  • Cleaning supplies
  • Coffee
  • Dining table
  • Free parking
  • Hangers
  • Kitchenette
  • Dedicated workspace
  • Long term stays allowed
  • Outdoor seating
  • Playground nearby
  • Wine glasses
  • Jacuzzi

4.3 · 19 reviews

A

Abraham S.

August 2026

I highly recommend this place for anyone looking for a private venue for large family gatherings. Indoors, there is a large room with plenty of dining tables, chairs, and couches to accommodate many guests. The air conditioning works perfectly throughout the property. Outdoors, there are numerous seating areas and beach chairs located under the sun, on the covered porch, around the fire pit, near the trampoline, and next to the pool. The property offers great activities, including a clean pool, a hot tub, a fire pit, a large ground area for games, and an exceptional number of grills. The cleanliness and hygiene are five-star and above any expectation, and the host is extremely friendly and accommodating. Close to shopping and food,
T

Trisha B.

March 2026

Shannon was such a great host! She was super responsive and accommodating before and throughout our entire stay. Our group of 10 adults and 4 littles had more than enough space to sleep and hangout especially in the huge retreat like living room. There were even tiny beds, high chairs, and a little table with chairs for our little ones. Everyone enjoyed their time. Thanks again Shannon!
J

Jennifer D.

1 week ago

The size was perfect for our group. The rooms and bathrooms were clean. It would be nicer with minor maintenance and a clean hot tub. The host was very responsive and was able to send a delivery of items we needed.

Where you’ll be

Chester, New York 10950, United States

Chester, New York, United States
41.375665-74.1993969
Timezone: America/New_York

Things to know

Cancellation policy

Free cancellation up to 30 days before check-in. 50% refund up to 7 days before. No refund after that.

Property rules

Pets not allowed

No smoking - fees will apply

Events not allowed

Safety & security

Check-in after 4:00 pm

Check-out before 11:00 am

16 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Oct 25, 2026$400Available
Oct 26, 2026$400Available
Oct 27, 2026$400Available
Oct 28, 2026$400Available
Oct 29, 2026$684Not Available
Oct 30, 2026$909Not Available
Oct 31, 2026$850Available
Nov 1, 2026$500Available
Nov 2, 2026$500Available
Nov 3, 2026$650Available
Nov 4, 2026$650Available
Nov 5, 2026$948Available
Nov 6, 2026$1155Available
Nov 7, 2026$1200Available
Nov 8, 2026$800Available
Nov 9, 2026$800Available
Nov 10, 2026$900Available
Nov 11, 2026$900Available
Nov 12, 2026$700Available
Nov 13, 2026$1112Not Available
Nov 14, 2026$1042Not Available
Nov 15, 2026$564Available
Nov 16, 2026$700Available
Nov 17, 2026$700Available
Nov 18, 2026$700Available
Nov 19, 2026$900Available
Nov 20, 2026$1100Available
Nov 21, 2026$1100Available
Nov 22, 2026$1000Available
Nov 23, 2026$1000Available
Nov 24, 2026$1125Available
Nov 25, 2026$1200Available
Nov 26, 2026$1200Not Available
Nov 27, 2026$1200Not Available
Nov 28, 2026$1200Available
Nov 29, 2026$897Available
Nov 30, 2026$904Available
Dec 1, 2026$832Available
Dec 2, 2026$839Available
Dec 3, 2026$952Available
Dec 4, 2026$1140Available
Dec 5, 2026$1145Available
Dec 6, 2026$850Available
Dec 7, 2026$818Available
Dec 8, 2026$739Available
Dec 9, 2026$712Available
Dec 10, 2026$890Available
Dec 11, 2026$1123Available
Dec 12, 2026$1200Available
Dec 13, 2026$797Available
Dec 14, 2026$783Available
Dec 15, 2026$832Available
Dec 16, 2026$890Available
Dec 17, 2026$1030Available
Dec 18, 2026$1200Available
Dec 19, 2026$1200Available
Dec 20, 2026$1200Available
Dec 21, 2026$1200Available
Dec 22, 2026$1627Available
Dec 23, 2026$1400Available
Dec 24, 2026$1400Available
Dec 25, 2026$1400Available
Dec 26, 2026$1400Available
Dec 27, 2026$1400Available
Dec 28, 2026$1400Available
Dec 29, 2026$1400Available
Dec 30, 2026$1400Not Available
Dec 31, 2026$1400Not Available
Jan 1, 2027$1400Not Available
Jan 2, 2027$1400Available
Jan 3, 2027$1400Available
Jan 4, 2027$1400Available
Jan 5, 2027$1200Available
Jan 6, 2027$1100Available
Jan 7, 2027$1100Available
Jan 8, 2027$1100Available
Jan 9, 2027$1100Available
Jan 10, 2027$1100Available
Jan 11, 2027$927Available
Jan 12, 2027$928Available
Jan 13, 2027$907Available
Jan 14, 2027$934Available
Jan 15, 2027$1100Available
Jan 16, 2027$1100Available
Jan 17, 2027$1100Available
Jan 18, 2027$1028Available
Jan 19, 2027$953Available
Jan 20, 2027$938Available
Jan 21, 2027$985Available
Jan 22, 2027$1100Available
Jan 23, 2027$1100Available