
House holiday rentals in Poughkeepsie
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Top-rated house rentals in Poughkeepsie
Guests agree: These houses are highly rated for location, cleanliness and more.

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, and 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!

Newly Renovated & Comfortable Home-Vassar/Marist
Leave the busy city and the hustle and bustle behind. Relax and rejuvenate yourself in the Hudson Valley. This retreat has all the amenities (fully equipped kitchen, spacious deck/backyard, fire pit, grill, and parking on premises available). Take a walk or bike ride at the Hudson Valley Rail Trail, hike at Mt. Beacon, explore Dutchess Wine Trail c/o Clinton Vineyards, shop at the Poughkeepsie Galleria, or relax at Hand and Stone Massage. There is so much for you, family and friends to do.

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.

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.

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

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

The Atala
The Atala is a two story 3BR/2Bath house, nestled in a quiet neighborhood close to the city's excitement and attractions. Warm up by the fireplace in the living room while watching your favorite shows on a 75” flat screen TV, or brew a cup of coffee in our convenient coffee bar. Enjoy three inviting bedrooms with air conditioning/heating and a fully equipped kitchen. Our backyard with furniture, fire pit, and gas grill, is perfect for relaxing with family and friends.

Hudson Valley Hygge House~ comfort in the country!
Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!

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)
Popular amenities for Poughkeepsie house rentals
House rentals with a pool

midcentury mod * POOL * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

Scenic River View Escape | New Paltz

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Highwoods Haven | saltwater pool and hot tub

Hudson River Sunset Getaway

Design Farmhouse w/ Pool + Firepit | Hudson Valley

Cozy & Spacious Country Home - All Seasons
Weekly house rentals

Summit Sanctuary: EV Ready Mountain Views

3000 sq ft Poughkeepsie home with chef's kitchen

Balmville Mid-Century Gem & Work From Home Retreat

Hudson Escape W/ Hot Tub + Bridge View

Rustic Swedish Barn/Featured in Airbnb Magazine

Hyde Park Luxury A-Frame - Pool/Chef Kitchen

Village Cape Getaway

Charming 3 Bedroom Home - Near Vassar, Marist
Private house rentals

The Hudson Valley Hideaway

Hudson Valley Retreat • CIA • Great Location!

Zen Peaks Retreat

Hollow Road House 4 Bathrooms & Game Room!

Charming Hyde Park Retreat|Minutes from Vanderbilt

Charming Townhouse in Historic District

House Under The Walkway

The Daydream: Hudson River Views, 4 bedrooms & Gym
When is the best time to visit Poughkeepsie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $134 AUD | $188 AUD | $171 AUD | $163 AUD | $196 AUD | $196 AUD | $196 AUD | $198 AUD | $189 AUD | $201 AUD | $144 AUD | $140 AUD |
| 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 holiday rentals
Explore 50 holiday rentals in Poughkeepsie

Nightly prices starting at
Poughkeepsie holiday rentals start at $57 AUD per night before taxes and fees

Verified guest reviews
Over 3,590 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Poughkeepsie holiday rentals include Wi-Fi access

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

4.8 Average rating
Poughkeepsie stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Rentals with a fire pit Poughkeepsie
- Rentals with pools Poughkeepsie
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