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Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.

Photo gallery for Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.

The front door leads to a porch, patio, and small yard.
Living room with electric fireplace, large TV, & retractable ceiling fan.
Dinette with bar stools.
A refrigerator, microwave, and wine rack are included.
Private kitchen

Reviews

9.2 out of 10
Wonderful
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Air-conditioning
  • Outdoor barbecue
  • Deck or patio

Explore the area

View map
Cortlandt Manor, NY
  • Place, Regal UA Cortlandt Town Center
    ‪2 min drive‬
  • Place, Woodbury Common Premium Outlets
    ‪33 min drive‬
  • Place, LEGOLAND® New York
    ‪47 min drive‬
  • Airport, White Plains, NY (HPN-Westchester County)
    ‪42 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Outdoor play area
Garden
Dining area

About this property

Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.

Newly remodeled 2 bed/1 bath backyard guesthouse with a patio, small porch, and yard. It includes a patio table that gets lots of sun (umbrella included), a small play area for young children, and a full-sized picnic table in the yard that sits under some trees.

Two TVs with Prime, HBO max, Disney, and Netflix, as well as games, books, and puzzles for your enjoyment. Close to Peekskill, West Point, Bear Mtn, Harriman, Appalachian Trail, & Hudson & Croton Rivers.

The Cottage is a separate dwelling that sits in our backyard in a residential neighborhood that is in a suburb of the greater NYC area. Living on the property enables us to quickly manage issues that may arise and try to make ourselves available for any questions about the area, etc. To allow our guests as much privacy as possible, a privacy wall was added.

Please be aware that we have a poochon who likes to let guests know that he is there. Although we keep him on a leash or in a gated area, at times he has gotten out. He's very friendly with kids, and kids typically love him.

Also, one of our neighbor's chicks grew into a rooster. We have no control over the animals of our neighbors. To counter the noise he might make while guests are trying to sleep (and to help promote sleep for our guests), each bedroom has a white noise machine or fan that should drown out the majority of any noise. If you are very sensitive to noise, however, please consider bringing earplugs.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Bring a gate for young children.
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit one pet total)
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Remove personal items and remove leftover food and drinks
Don't bother making the beds. The cleaners will strip them anyway.
Please discard any opened/ used milk containers.
Leave the key on the counter and the door unlocked.
Failure to complete these may result in a negative review from the host.
Keep kids off the stair railings. Children <12 must be monitored while playing in the yard, swingset, and near the pond/brook.
TP ONLY in the toilet. All used feminine hygiene products, wet wipes, or baby wipes MUST be thrown into a trash receptacle.
Any lost remote controls will lead to $200 penalty per remote to replace the item and time incurred reprogramming the corresponding device(s).

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a first aid kit and a deadlock

About the area

Cortlandt

Cortlandt is home to this holiday home. Bear Mountain State Park and Franklin D. Roosevelt State Park reflect the area's natural beauty and area attractions include Hudson Valley Center for Contemporary Art and Paramount Hudson Valley Theater. Travelling with kids? Consider Lincoln Depot Museum, or check out an event or a game at Christl Arena. Take in the nearby slopes with cross-country skiing and skiing, or try out other outdoor activities such as ice skating and sledging.
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Map
Cortlandt Manor, NY

What's nearby

  • Regal UA Cortlandt Town Center - 2 min drive - 1.5 km
  • Bear Mountain State Park - 16 min drive - 15.5 km
  • United States Military Academy - 18 min drive - 18.1 km
  • Woodbury Common Premium Outlets - 33 min drive - 35.7 km
  • LEGOLAND® New York - 47 min drive - 55.8 km

Getting around

  • Peekskill - 8 min drive
  • Newburgh, NY (SWF-Stewart Intl.) - 42 min drive

Restaurants

  • ‪McDonald's - ‬2 min drive
  • ‪Nonna's Brick Oven Pizzeria & Restaurant - ‬20 min walk
  • ‪Panera Bread - ‬18 min walk
  • ‪Starbucks - ‬12 min walk
  • ‪Jersey Mike's Subs - ‬2 min drive

Frequently asked questions

Is Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails. pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much does it cost to stay at Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.?

As of 1 May 2026, prices found for a 1-night stay for 2 adults at Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails. on 4 October 2026 start from NZ$454, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.?

On-site parking is available at the property.

What time is check-in at Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.?

Check-in begins at 4:00 PM.

What time is check-out at Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.?

Checkout is at 11:00 AM.

Where is Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails. located?

This family-friendly Cortlandt holiday home is within 2 mi (3 km) of New York - Presbyterian / Hudson Valley Hospital, Hudson Valley Center for Contemporary Art and NewYork-Presbyterian Hudson Valley Hospital. Paramount Hudson Valley Theater and Lincoln Depot Museum are also within 3 miles (5 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 22 out of 29 reviews
Rating 8 - Good. 2 out of 29 reviews
Rating 6 - Okay. 4 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 1 out of 29 reviews

9.8/10

Cleanliness

9.0/10

Amenities

10/10

Property conditions & facilities

9.8/10

Check-in

9.4/10

Communication

8.6/10

Location

8.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Patrick M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Friendly host, clean property.
Stayed 5 nights in Feb 2026
Verified

10/10 Excellent

Stephanie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was just as listed, located in a convenient place to visit our cadet at West Point. There were stores & restaurants close by and everything we needed was provided. The beds were comfortable & parking was right outside. A nice stay!
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Ann K.

Liked: Cleanliness, check-in, location, listing accuracy
The interior of the cottage was beautifully finished with great attention to detail taken!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Jim M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and nicely appointed, good neighborhood, close to amenities.
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Carrie K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Would stay here again-perfect!

Clean, organized, wonderful booklet filled with great recommendations on what to do and see in the area. Felt like home away from home!
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

James B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Cottage

Great place to stay. Very accessible to any shopping needs and to West Point. There is limited space for 4 to sit if it’s raining outside. Overall, great spot to stay!
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Olena

Liked: Cleanliness, amenities, property conditions & facilities, communication
A wonderful house, cozy and clean. A quiet and safe place where you can relax from the hustle and bustle of the big city. The house has everything you need for a comfortable stay. We had a wonderful rest!
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Katherine K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing

Stay was absolutely wonderful, property was lovely and super easy to get to and from sleepy hollow. Definitely recommended.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Shaunna

Liked: Cleanliness, amenities, property conditions & facilities
Quiet neighborhood close to local attractions. Plenty of room for our family of four. Very clean. Very nice outdoor space. Everything we needed in the cottage.
Stayed 2 nights in Aug 2024
Verified

8/10 Good

Dan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Short getaway

I thought the property was really nice, upgraded, and we had a great time, only issue i had was the wifi was weak so my apps kept buffering, but not a huge deal, the place has everything you need. A small little yard if you bring your dog and a seating area outside. Overall a really nice stay
Stayed 3 nights in Nov 2024
Verified

10/10 Excellent

Jodie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peekskill cottage

My friend and I had a wonderful stay in the cottage! It had everything we needed and was so cozy. I highly recommend it!
Stayed 4 nights in Jun 2022
Verified

10/10 Excellent

Taryn B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

West Point Graduation

We had a wonderful stay. The property was exactly as advertised and the location was great. Instructions throughout the home were clear and we had no issues with our stay. Thank you for making the weekend smooth and easy!!
Stayed 5 nights in May 2024
Verified

10/10 Excellent

Mike R.

Liked: Cleanliness, check-in, communication, location

Tiny but just enough

We spent 2 nites for graduation weekend at West Point. It turned to be a convenient location. The cottage had everything we needed. 👍
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Donna T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable

Homeowner responded promptly to inquiries. Property was well prepared.
Stayed 3 nights in Nov 2024
Verified

10/10 Excellent

christy m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Army moms and daughters

Loved it!!
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Jessica W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay at the cabin

The property was clean, excellent condition, and up to date. Had everything we needed for our stay. Including shampoo, soap, plates, snack, and so much more. They thought of all the things someone would need if they forgot anything. It was cute little cottage and was perfect for my families stay!
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Stacey D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Westminster Dog Show

We drove in from Michigan for the Westminster dog show . This listings worked great with stores and restaurants close by and easy access to Hwy for traveling . We plan to return and next year.
Stayed 3 nights in Jun 2022
Verified

10/10 Excellent

Rick M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Strategic location

Our stay at the cottage filled the bill for a comfortable and convenient home base for exploring the lower Hudson Valley. The hosts were efficient and responsive. The cottage is compact but well laid out for four people. Little touches like ambient lighting in the main room were nice touches.
Stayed 5 nights in Oct 2022
Verified

10/10 Excellent

Martina H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Worked well for me and my spouse.

All was well. Fast communication response.
Stayed 8 nights in Sep 2023
Verified

8/10 Good

Kathryn S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

West a point visit

The home was very clean and had everything we needed - snacks games and a cute patio. The internet was iffy and never worked to stream on the bedroom tv. They came and checked it , but it didn’t improve. The host was very responsive and offered to ship an item our daughter left. We would rent again.
Stayed 4 nights in Oct 2024
Verified

10/10 Excellent

David H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hudson Valley Nest

We enjoyed staying in this neat cottage with many clever custom features. It convenient to West Point, the spectacular Croton Gorge damn, and many amazing views. A very large supermarket is a short drive away as well as many restaurants. The owners provide many thoughtful small amenities. We thought the neighbor's rooster was very charming and not much louder than a crow or other wild birds. You can't hear it over the air conditioning during the day and it is quiet at night.
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Marianne M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy, clean, and comfy

The cottage was quite new, with a well-appointed kitchen in a compact space. The living area was cozy and comfortable as was the bedroom. We didn’t use the second bedroom upstairs, although we went up there and it was quite roomy. (It would be difficult to bring luggage up the spiral staircase.) The cottage has a cute front porch, and there is a patio seating area just off the porch for sitting or dining. Great location—quiet and also close to shopping, restaurants, Bear Mountain Parkway.
Stayed 4 nights in Jul 2022
Verified

6/10 Okay

Geri W.

Liked: Cleanliness, check-in, communication, listing accuracy

Not the best

The inside lights flicker constantly if water is turned on. Owner was aware. The house is comfortable for 2 people. Amenities have restrictions, just be aware. We had clothes to wash but our 5 day stay did not qualify for us to use it. Many instruction posted throughout the cottage.
Stayed 5 nights in Jul 2024
Verified

6/10 Okay

Sandy S.

Liked: Cleanliness, check-in, communication
Disliked: Location

Short Stay

The property outside of the apartment was an absolute mess. The cottage - needs to be represented that way, was extremely clean inside and well stocked but with 4 adults it was way too small inside. Luckily, we had nice weather so could be outside. It was incredibly expensive and was upset that we were asked to pay $15 PER USE of the grill. I think out of everything that upset me the most. We paid (after fees and taxes) just under $700 for two nights and we didn’t get use of the grill for no extra charge.
Stayed 2 nights in Aug 2022
Verified

6/10 Okay

Alyson S.

Liked: Check-in, communication
Disliked: Cleanliness, location, listing accuracy

2 night trip

The property manager could not have been any nicer, communicated effectively, provided her cell phone number, provided a high chair, and even provided a ride on toy for my son. The only reason this wasn’t a 5-star rating is I felt the listing does not appropriately show what you are renting as far as the location. The listing shows a cottage that seems to not be in close distant to any other property, however, the cottage is in the backyard of another house, there’s an active business on the property, people walking around all day, and miscellaneous broken down items and tools throughout the surrounding property. The cottage itself and absolutely beautiful, however, I would have liked to know fully what we were renting as we were really looking for a quiet somewhat private getaway.
Stayed 2 nights in Aug 2022

About the host

Hosted by Patricia Sayre

Host profile image
My husband and I co-host this property. When we aren't hosting guests, we enjoy taking hikes or canoeing in the area.

Why they chose this property

This property is maintained throughout the year and comes with a well-equipped kitchen. Easy drive to bucolic settings offering hiking trails, rivers, marshes, and local sites such as West Point, The Great Jack O'Lantern Blaze, Boscobel, The Hudson Valley Shakespeare Festival, Van Cortlandville Manor, and The Appalachian Trail. The City of Peekskill is less than 1 mile away, and the Peekskill Riverfront park/train station is approximately 2 miles away.

What makes this property unique

This area has numerous things for you to do throughout the year, such as golfing at one of the local public golf courses, and horseback riding on one of the local trails (see NYS parks guide for a listing of horse-approved trails). Other options include skiing, golfing, seeing a show or game, or taking a tour of West Point.
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