
House holiday rentals in Poughkeepsie
Find and book unique houses on Airbnb
Quick stats about house rentals in Poughkeepsie

Total holiday rentals
Explore 40 holiday rentals in Poughkeepsie

Nightly prices starting at
Poughkeepsie holiday rentals start at $52 SGD per night before taxes and fees

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

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Poughkeepsie holiday rentals include wifi 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!
Top-rated house rentals in Poughkeepsie
Guests agree: these houses are highly rated for location, cleanliness and more.

3 Bedrooms close to Rhinebeck NY
Watch the sunset from the patio or just enjoy the evening sitting on the enclosed front porch. With in walking distance to state parks and centrally located between Rhinebeck NY and Hyde Park NY. They are a short 10 minute drive away. Rhinebeck offers multiple shops, restaurants and historic sites. Hyde Park is home to the Culinary Institute and it’s many restaurants as well as FDR estate. You are within walking distance to our local library, park, River & Post restaurant and pickleball court.

This New House
Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

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 house rentals in Poughkeepsie
House rentals with a pool

midcentury mod * POOL * walk out trail R2R /TOWN

Entire Home (private pool), Event Friendly

Scenic River View Escape | New Paltz

Hudson River Sunset Getaway

Upstate Modern Scandinavian Barn in the Catskills

New Paltz dog friendly retreat w/ salt water pool

Luxury Prvt Estate w/Hot Tub+Gameroom nr Rhinebeck

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Weekly house rentals

Mindful Escape: Theater, Trails, Wood Stove

Slate Cabin - Stylish Country Escape x Rhinebeck

Historic 1 BR Family Home Near Buttermilk Falls

Modern creekside cabin in the Catskills

Cook House, Modern Cottage with Hot Tub

Modern House with Mountain View @Getawind

Hyde Parks Hideaway

Newly Renovated & Comfortable Home-Vassar/Marist
Private house rentals

The Hudson Valley Hideaway

View House

Historic Spacious Home 5 bed/2 bath

3000 sq ft Poughkeepsie home with chef's kitchen

Zen Peaks Retreat

Hudson Escape W/ Hot Tub + Bridge View

Charming Townhouse in Historic District

Charming Hyde Park Retreat|Minutes from Vanderbilt
When is the best time to visit Poughkeepsie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $171 SGD | $189 SGD | $186 SGD | $149 SGD | $180 SGD | $180 SGD | $180 SGD | $181 SGD | $173 SGD | $184 SGD | $132 SGD | $128 SGD |
| 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 |
Destinations to explore
- New York City Holiday rentals
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- Rentals with a patio Poughkeepsie
- Family-friendly rentals Poughkeepsie
- Apartment rentals Poughkeepsie
- Rentals with a fireplace Poughkeepsie
- Rentals with outdoor seating Poughkeepsie
- Pet-friendly rentals Poughkeepsie
- Flat rentals Poughkeepsie
- Cabin rentals Poughkeepsie
- Rentals with a washing machine and dryer Poughkeepsie
- Rentals with a firepit Poughkeepsie
- Rentals with pools Poughkeepsie
- House rentals Dutchess County
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- House rentals United States
- Hunter Mountain
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Zoom Flume
- Taconic State Park
- Brotherhood, America's Oldest Winery
- Hunter Mountain Resort
- Mohonk Preserve
- Kent Falls State Park
- Mohawk Mountain Ski Area
- Walkway Over the Hudson State Historic Park
- Mount Peter Ski Area
- Storm King Art Center
- Wawayanda State Park
- Hudson Chatham Winery





