
Vacation rentals in Poughkeepsie
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Top-rated vacation rentals in Poughkeepsie
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Large, private apartment in scenic Hudson Valley
We are located right in the middle of the Dutchess County so access to all points is convenient. Many attractions are: historical Hyde Park, Walkway Over The Hudson, Culinary Institute, Vassar & Marist colleges, wineries, breweries, the quaint towns of Millbrook & Rhinebeck, Dutchess County Fairgrounds, and The Links At Unionvale golf course and banquet hall. Great for couples, adventurers and business travelers who love activity but appreciate a comfortable quiet place at the end of the day.

Serene Waterfront Mill House, Stroll to Village
Sweet 1840 mill house on the water, nature-filled back deck yet 5 mins walk to antiquing & excellent Millbrook restaurants. Make this your base as you explore the beautiful Hudson Valley. Or relax out back & enjoy the birds & stream. Farmhouse antique shabby chic decor with king tempurepedic bed in large second floor master BR, two BRs with twin trundle beds, 1 bathroom upstairs & 1 down, A/C, ceiling fan, cozy woodstove, wifi with smart tv, eat-in kitchen, coffee/tea, plenty of free parking.

Little Yellow Cottage New Paltz - Kitchen wash/dry
Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Fabulous Lemon Cottage in Rhinebeck, NY
This cozy, clean, and light-filled cottage with its bedroom loft provides a perfect getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from Rhinebeck village, but also close to Red Hook, Bard, Kingston, Woodstock, Hudson, etc. Use our guidebook to explore the area, or choose to stay in at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

Acorn Hill Cottage -A mid century farmhouse gem
No list of chores. Just relax! Now accepting dogs on a case by case basis. Must inquire PRIOR TO BOOKING. Minutes to historic Rhinebeck Village, this quaint abode makes for the perfect romantic or mind clearing get away. Located directly off Route 9 tucked in the trees. Enjoy our completely separate art filled cottage. The open 550sq/ft studio floor plan will cheerfully accommodate couples & close friends. 4 persons MAX. Best suited for adult guests as the space is not child proofed.

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

Lake Side Tiny House
Reconnect with nature at this unforgettable escape. Sitting on the back side of beautiful 5 acre property, tucked in the woods along a beautiful lake. The Hosts home in on the property Come stay and unwind. Plenty to explore and just be. Lake access for swimming or with paddle board, canoe, or kayak. Just ask and can be assisted with. The whole property has been curated to be a magical oasis. Full bathroom inside Brand new Mini Split heat and AC unit. Has most kitchen amenities

3 Bdrm. Near Hudson Valley Colleges & Attractions
Built in 1910, this 3 bedroom apartment is located close to many Hudson Valley attractions - only 0.5 miles from the Poughkeepsie train station. Located within 2 miles of both Marist and Vassar Colleges, as well as a short drive from The Culinary Institute of America. Historic villages of Hyde Park and Rhinebeck are just a short drive along the river. As well as fast access to hiking and biking trails in local Shawangunk mountains, Mohonk Preserve, and Minnewaska State Park.

Suite of Rooms in Historic Home
Wonderfully decorated 3rd floor suite of rooms in the Academy Historic District. Two Newly renovated bedrooms, one with queen bed, the other with 2 twin beds. There is an additional day bed in the living area/ sitting room space , a TV with Netflix & Amazon Prime with wifi connection throughout. The bathroom has modern fixtures and a claw-foot tub/shower. There is a private entrance with additional half bath . A private porch and use of the beautiful backyard.

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

The Harvest Guest House~ Hidden Gem with Pool
Reconnect with yourself & nature. The Georgian style home is set on 6 wooded acres and surrounded by rugged rock ledges, minutes to Marist, The Culinary, Roosevelt & Vanderbilt estates. THE HARVEST GUEST HOUSE offers a genuine Hudson Valley stay. Your suite has its own private entrance, bathroom & fireplace. Enjoy a comfortable place to unwind after exploring nearby trails, river towns, and historic sites. Relaxed, real, and rooted in nature.

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 vacation rentals
Stay near Poughkeepsie's top sights
Other great vacation rentals in Poughkeepsie

Our Place - A Big Little House

Creekside Cottage

This New House Two

The Atala

Fully stocked creekside sauna retreat with privacy

Cottage on the Creek

Charming home near Walkway Over The HUDSON

4BR|2Bath|King Beds|Walk to Marist|CIA|Pet|Parking
When is the best time to visit Poughkeepsie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ349 | ﺩ.ﺇ422 | ﺩ.ﺇ430 | ﺩ.ﺇ422 | ﺩ.ﺇ481 | ﺩ.ﺇ496 | ﺩ.ﺇ485 | ﺩ.ﺇ503 | ﺩ.ﺇ470 | ﺩ.ﺇ514 | ﺩ.ﺇ485 | ﺩ.ﺇ470 |
| 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 |
Frequently Asked Questions
What are the best places to stay in Poughkeepsie?
Explore stays near the historic downtown for walkable cafés, art spaces, and riverfront views, or choose neighborhoods around the college for a lively, academic vibe. The surrounding countryside has peaceful retreats in more rural settings.
What are the best things to do in Poughkeepsie with kids?
Poughkeepsie has interactive museums, playgrounds, and parks where kids can move and learn. Many families enjoy the Walkway Over the Hudson for fresh air, or get curious at local science and nature centers.
What are some of the best things to do in Poughkeepsie?
Explore the Walkway Over the Hudson for sweeping river views, stroll through the Locust Grove Estate, or discover art at independent galleries. The city also has locally owned cafés, public gardens, and nearby hiking paths.
How is the weather in Poughkeepsie?
Poughkeepsie experiences cold winters with temperatures around 16–35°F (-9–1°C) in January and warm, humid summers peaking near 82°F (28°C) in July. Spring and fall bring mild days, changing leaves, and frequent rainfall.
When is the best time to visit Poughkeepsie?
Late spring and early autumn are often recommended, with mild temperatures, blooming gardens, and colorful fall foliage. Summer brings outdoor events, while winter has a quieter charm for those who enjoy crisp air and bundled walks.
What are the best places to visit in Poughkeepsie?
The Walkway Over the Hudson is often recommended for panoramic perspectives, while the Frances Lehman Loeb Art Center highlights diverse visual arts. Locust Grove Estate shares regional history, and local markets provide a taste of community life.
What are some hiking trails in Poughkeepsie?
Explore the Walkway Over the Hudson for an accessible, elevated experience, or follow wooded routes in the nearby Mohonk Preserve. Vassar Farm and Ecological Preserve has gentle trails through fields and wetlands.
What are some family activities we can do in Poughkeepsie?
Families often enjoy the Mid-Hudson Children’s Museum, outdoor fun at local parks, and hands-on experiences at the science center. The riverfront is great for picnics, bike rides, and playground time.
What are some of the best day trip ideas from Poughkeepsie?
Many travelers explore the arts scene in Beacon, sample local foods at surrounding farms, or hike forest preserves around the Hudson Valley. Storm King Art Center has outdoor sculpture exhibits set in open landscapes.
Are there any pet friendly accommodations available in Poughkeepsie?
Many places around Poughkeepsie welcome pets, especially in neighborhoods near parks or green spaces. Several hosts highlight pet-friendly amenities, making it easier to bring your companion along.
What are some local tips for visiting Poughkeepsie?
Layer clothing to adjust to changing temperatures, especially in transitional seasons, and explore early in the day to enjoy quieter parks and scenic walks. Many cafés and shops are locally owned, so take time to ask staff for neighborhood tips.
What is Poughkeepsie known for?
Poughkeepsie is known for its location on the Hudson River, the Walkway Over the Hudson, and its blend of historic estates, academic institutions, and arts communities. The city has roots in early American industry and local food traditions.
What are the best hidden gems to explore in Poughkeepsie?
Explore independent bookshops, wander along quiet riverfront parks, or visit Springside, a historic landscape known for its architecture and natural scenery. Local galleries and seasonal farmers markets often reveal more about Poughkeepsie's creative and agricultural spirit.
What are the best foods to try in Poughkeepsie?
Poughkeepsie has farm-to-table dining, classic diner fare, and regional specialties like apple desserts, locally roasted coffee, and New York-style pizza. Markets and delis often feature cheeses, breads, and pastries from nearby farms.
What should I bring for a trip to Poughkeepsie?
Pack layers for shifting weather, a rain jacket, and comfortable shoes for walking city streets and park trails. Reusable water bottles and a camera are useful for exploring outdoor viewpoints and local markets.
What is the nightlife in Poughkeepsie like?
Nightlife in Poughkeepsie features live music venues, cozy pubs, and cafés that host open mic or poetry nights. Some neighborhoods have casual bars and lounges with local brews and occasional performances.
What are the most popular events or festivals in Poughkeepsie?
Poughkeepsie has seasonal festivals celebrating local food and crafts, outdoor concerts at city parks, and arts fairs that draw a regional crowd. Parades and riverfront celebrations are often suggested in summer and during holidays.
Are there family friendly vacation rentals in Poughkeepsie?
Many vacation rentals in Poughkeepsie are described as family-friendly, with multiple bedrooms, kitchen facilities, and proximity to parks or playgrounds. Hosts often share guidance on nearby family activities.
Quick stats about vacation rentals in Poughkeepsie

Total vacation rentals
Explore 100 vacation rentals in Poughkeepsie

Nightly prices starting at
Poughkeepsie vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 6,970 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Poughkeepsie rentals

4.7 Average rating
Poughkeepsie stays receive an average rating of 4.7 out of 5 from guests
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- Minnewaska State Park Preserve
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- Butternut Ski Area and Tubing Center
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- Bash Bish Falls State Park
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