
House vacation rentals in Poughkeepsie
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Top-rated house rentals in Poughkeepsie
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Slate Cabin - Stylish Country Escape x Rhinebeck
This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.
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.

The Cozy Cape In Historic Hyde Park
Modern amenities meets early 20th century charm in our cozy, totally renovated space situated in the hearth of the historic town of Hyde Park and adjacent to the Hudson River. Built in the 1940s, our Cozy Cape is nestled in a quiet neighborhood off of Route 9 & is central to historic sites, shopping, parks, and dining options. Our home is also minutes by car to the Culinary Institute Of America, Walkway Over The Hudson, wineries, antique shops, Marist and Vassar colleges & Town of Rhinebeck!

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.

Hudson Valley Farmhouse | Winery & Hiking Getaway
Tucked into the Hudson Valley, our restored 1873 farmhouse is made for slow mornings, fresh coffee, and easy weekends between hiking trails and nearby wineries 🌿 This is a private 3BR/2.5 bath first-floor unit within a shared home. Designed for a calm, quiet stay. Only registered guests are permitted on the property. Located in Marlboro near Beacon, New Paltz, Kingston West Point, Vassar, Marist, Warwick & Wallkill with a garden to enjoy and harvest fresh herbs and seasonal vegetables.

Tranquil Tree-House on the beautiful Hudson River
Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door. We have added a separate kitchenette additional crockpot and induction cooktop.

3Br Hilltop Ranch on 130acre farm w/ falls & creek
Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

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!

Nature Retreat with Pond Views and Fire Pit
Nestled among the trees, this bright and serene home is off a quiet road just minutes outside the village of Rhinebeck. The house features lots of light, direct pond view, indoor fireplace, and renovated kitchen. We offer a great value while providing high-end amenities like luxury linens and towels, hybrid memory foam beds, and down pillows and comforters. This home sleeps eight (and up to ten with the two rollaway beds) and is the perfect getaway for a group trip or family stay.

Charming home near Walkway Over The HUDSON
Totally renovated home conviently located near by train station, Marist College, Vassar College, Culinary Institute of America, FDR Library, Walkway over the Hudson. My home is a 2 story home built in 1856; it has one bedroom and full bathroom on each floor. We refinsihed 9 inch pine wood floor trying to keep most of yesterday in the house. kitchen is fully equipped with snacks and coffee, tea! SORRY WE DO NOT PROVIDE BREAKFAST WIFI WITH SMART TV ONLY (NO CABLE) 2 parking spaces

4BR|2Bath|King Beds|Walk to Marist|CIA|Pet|Parking
This home is located in the Mid Hudson Valley -just steps away from Marist U, The entrance to Walkway Over the Hudson, MHR Hospital and a 2mi ride to the CIA! Equipped with a full kitchen, king beds, 2 full baths, Roku TV, private parking & spacious backyard- perfect for grilling or cozying up next to the fire pit. Make this cheerful house your home base as you explore all the wonders of the Hudson Valley! We are a small dog friendly! (15 lbs or less)

Honeybug Snug near Omega Institute!
Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.
Popular amenities for Poughkeepsie house rentals
House rentals with a pool

Entire Home (private pool), Event Friendly

Scenic River View Escape | New Paltz

Highwoods Haven | saltwater pool and hot tub

Hudson River Sunset Getaway

Design Scandi Retreat, Heated Pool, Dogs Welcome

Upstate Modern Scandinavian Barn in the Catskills

New Paltz dog friendly retreat w/ salt water pool

Catskill Retreat: Heated Pool, Hot Tub, Sauna!
Weekly house rentals

The Hudson Valley Hideaway

View House

3000 sq ft Poughkeepsie home with chef's kitchen

Hudson Escape W/ Hot Tub + Bridge View

Modern creekside cabin in the Catskills

Eclectic one-bedroom house

Charming Townhouse in Historic District

Modern House with Mountain View @Getawind
Private house rentals

Architect-Designed Modern Barn Retreat + Hot Tub

Historic Spacious Home 5 bed/2 bath

Summit Sanctuary: EV Ready Mountain Views

Luxe Wooded Modern Getaway, Saltwater Pool + Spa

Zen Peaks Retreat

Hollow Road House 4 Bathrooms & Game Room!

Charming Hyde Park Retreat|Minutes from Vanderbilt

Cardinal Cottage
When is the best time to visit Poughkeepsie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$27,611 GYD | G$30,540 GYD | G$30,121 GYD | G$24,055 GYD | G$29,075 GYD | G$29,075 GYD | G$29,075 GYD | G$29,285 GYD | G$28,030 GYD | G$29,703 GYD | G$21,336 GYD | G$20,708 GYD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Quick stats about house rentals in Poughkeepsie

Total vacation rentals
Explore 40 vacation rentals in Poughkeepsie

Nightly prices starting at
Poughkeepsie vacation rentals start at G$8,367 GYD per night before taxes and fees

Verified guest reviews
Over 3,570 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Poughkeepsie vacation rentals include wi-fi access

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

4.9 Average rating
Poughkeepsie stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Windham Mountain
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Mohawk Mountain Ski Area
- Hunter Mountain Resort
- Taconic State Park
- Mount Peter Ski Area
- Bear Mountain State Park
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Wawayanda State Park
- Storm King Art Center
- Millbrook Vineyards & Winery
- Hudson Chatham Winery





