Poughkeepsie Vacation Homes

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Our top choices for Poughkeepsie holiday homes

A spacious living room with a fireplace, a dining area with a table and chairs, and a large window providing natural light.

1. Charming 2-bdrm house with AC, WiFi in Cherokee Village with amazing river views

Cherokee Village

Robert

HK$1,860 total

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a bed, a nightstand, a lamp, a door, and a wall with framed pictures.

2. Serene 1-bedroom tiny house in charming Strawberry, steps away from the creek

Strawberry

HK$1,378 total

includes taxes & fees

11 Nov - 12 Nov

A wooden swing with blue cushions and a 'relax' pillow, hanging from a window with string lights.

3. Many Moons Townhouse Heated Pool, Rivers, Lakes, and Golf Getaway

Cherokee Village

Anonymous traveller

HK$1,661 total

includes taxes & fees

18 Oct - 19 Oct

A single-story house with a front porch, a staircase leading to the entrance, and a small front yard.

4. Cute 2BR Full Vacation Home near Spring River and Waterfall

Cherokee Village

Keith

HK$1,017 total

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with a built-in stove, a dining area with wooden chairs, and a red curtain.

5. Private Dock! Lakefront Cherokee Village Retreat

Cherokee Village

HK$2,924 total

includes taxes & fees

18 Oct - 19 Oct

A kitchen with wooden cabinets, a built-in island with bar stools, a refrigerator, and a window with curtains.

6. Lake Thunderbird View - Signal Tree Cottage

Cherokee Village

Trisha W.

HK$1,881 total

includes taxes & fees

19 Oct - 20 Oct

A boat with a maroon canopy labeled "Sun Tracker" moving across a lake with houses and trees in the background.

7. Lake and boat life! Lake Rental in a dead-end street.

Cherokee Village

Ben R.

HK$2,144 total

includes taxes & fees

19 Oct - 20 Oct

A window with a view of a brick building and a paved area with red barriers.

8. Historic Carrie Tucker Cottage with view of Spring River in charming Hardy, Ark.

Hardy

Traci P.

HK$1,870 total

includes taxes & fees

26 Oct - 27 Oct

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Top Poughkeepsie Hotel Reviews

NEW LISTING:Spring River:Creek Cabin, Private Footage on South Fork Spring River

10/10 Excellent

"This was the cutest river cabin. It was clean and comfortable."

Vacation Condo #5 2BR with full kitchen, walk to river and shops, pets welcome

8/10 Good

"Overall, it was a good rental. The place itself, clean and roomy. Full kitchen which I didn’t take advantage of. It was quiet and peaceful. There is someone living above but the very occasional floor thumping (not loud or late) was not an issue. Good stuff. - location was perfect for me. If you want to explore downtown, it’s perfect. Casey’s is a minute away by car for coffee and gas. Corer both for breakfast is a 2 minute walk. Nothing special food wise but certainly decent. - it is roomy and when all is said and done… it’s beats the heck out of the two local motels (stayed in both, both are horrible but expensive for what you don’t get) - it’s easy to relax here. It’s comfortable Getting down to the nitty gtitty (didn’t have a significant impact on my stay). - some kind of guide for the TV setup. For me it came down to Netflix or Prime Video. Unable to watch any evening college or NFL football. Couldn’t find local or network news/weather - Bushes/plants out side the door need to be trimmed (way) back. The grass was long but it was mowed a couple days into my stay. I was asked to move my Truck for the mowing, beyond me why? I was there and it wasn’t a big deal but no one came and said I could move my Truck back. - don’t depend on the hand rail for the steps into the rental. It is not solid and moves around if you use it. - maybe a modern flat screen size wise? You can get a 52” for peanuts now. The one in the apt is maybe 36”? Would I stay here again? ‘YES”"

Charming 2-bedroom cabin with AC in cozy Poughkeepsie

10/10 Excellent

"The ONLY problem we ran into had nothing to do with the actual home. It was the drop pin link on the VRBO directions, but the actual address got us here just fine. Everything else was great! Thanks for a wonderful stay...Sorry we forgot to sign the guest book."

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