
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.
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.

Mindful Escape: Theater, Trails, Wood Stove
Exhale and recharge in this luxurious space at the foot of the Shawangunk Mountains. This gem features an open-concept kitchen and living room, perfect for connecting with nature. Enjoy the high-end Foster Leather Sofa, cozy movie nights on a 120" projector screen, and a wood-burning stove for chilly evenings. Every detail, from fresh linens to a meaningful library, is thoughtfully curated. Discover hidden messages throughout the house, inviting you to explore and unwind in this serene retreat.

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.

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!

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

Entire lake house to yourself. Great for groups
Spring is here, dock is in, boats are ready for you. Kitchen is set up to make big family meals and have the house entirely to yourself! new grill, new umbrella. New sleeper couch , new coffee maker. basement cleaned and repaint. Relax, enjoy the view from Screened in porch, pergola fire pit, or deck with gas bbq. Family games in Basement Rec room with pooltable, ping pong, darts.stay a while and remote work in style! Close to Kingston, new paltz, Rosendale. Ask about longer stays.

Hudson Valley Boutique Airb&b
Bring the whole family to this great place with lots of room for fun. Located in The Hudson Valley in close proximity to" Walkway over The Hudson" , New Paltz, Lake Minnewaska, Beacon, Poughkeepsie, New Paltz, and Woodstock ! Grill out on the back deck or visit one the wonderful local restaurants! Within 10 minute ride to Marist College, Vassar College, The Culinary Institute of America, And SUNY New Platz College.
Popular amenities for Poughkeepsie house rentals
House rentals with a pool

The Getaway-HOST & Co.

midcentury mod * POOL * walk out trail R2R /TOWN

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

New Paltz dog friendly retreat w/ salt water pool
Weekly house rentals

Honeybug Snug near Omega Institute!

Creekside cottage on 65 acres of land

The Stone House

Architect's Hudson Valley Home in the Woods

Contemporary Hudson Valley home

Mt. Wonder: Big Cozy Cabin with Wow View

Newly Renovated & Comfortable Home-Vassar/Marist

Architectural wonder in the woods
Private house rentals

The Hudson Valley Hideaway

Summit Sanctuary: EV Ready Mountain Views

3000 sq ft Poughkeepsie home with chef's kitchen

Zen Peaks Retreat

Hudson Escape W/ Hot Tub + Bridge View

Hollow Road House 4 Bathrooms & Game Room!

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 | $228 NZD | $252 NZD | $249 NZD | $198 NZD | $240 NZD | $240 NZD | $240 NZD | $242 NZD | $231 NZD | $245 NZD | $176 NZD | $171 NZD |
| 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 40 holiday rentals in Poughkeepsie

Nightly prices starting at
Poughkeepsie holiday rentals start at $69 NZD 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 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
40 of Poughkeepsie holiday 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





