Holiday houses in Poughkeepsie

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Top-rated holiday rentals in Poughkeepsie

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Guest favourite
A spacious living room features a comfortable sectional sofa, a wooden coffee table, and a cozy armchair. A large wall-mounted television is positioned above a wood-burning fireplace. Natural light filters in through multiple windows, highlighting the room's neutral decor and textured area rug.
Home in Hyde Park
4.91 out of 5 average rating, 136 reviews

The Cozy Cape In Historic Hyde Park

Modern amenities meets early 20th century charm in this 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

Top Guest favourite
Guest suite in Wappingers Falls
4.83 out of 5 average rating, 128 reviews

Private ground floor guest suite in Hudson Valley

Guest favorite/newly renovated/private, ground floor guest suite. Br/full bath/large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen. Car suggested.

Guest favourite
A living area features a comfortable sectional sofa adorned with cushions and a low wooden coffee table. Natural light fills the space through two windows, while a floor lamp provides additional illumination. The interior is accented by warm, earthy tones and wooden flooring.
Apartment in Stone Ridge
4.91 out of 5 average rating, 570 reviews

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

Guest favourite
A charming yellow cottage is set amidst a natural landscape, featuring a welcoming front porch with steps leading to the entrance. Soft lighting from the interior creates an inviting glow, while a decorative white dog figure adds a touch of whimsy to the exterior.
Cottage in Highland
4.89 out of 5 average rating, 680 reviews

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!

Top Guest favourite
A modern living area features a gray sofa adorned with patterned cushions. Two sleek black tables are positioned on a striped rug, with a small plant on one of the tables. Tall, dark curtains frame the window, allowing natural light to enter the space.
Condo in Poughkeepsie
4.97 out of 5 average rating, 353 reviews

Spacious and stylish entire one bedroom apartment.

Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

Guest favourite
Home in Staatsburg
4.99 out of 5 average rating, 116 reviews

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.

Top Guest favourite
A spacious bed with a white striped blanket is centered in the room, accompanied by two patterned pillows. A yellow accent chair and a small side table with a lamp are visible in the background, contributing to a cozy, inviting atmosphere.
Apartment in Poughkeepsie
4.95 out of 5 average rating, 133 reviews

Spacious Studio in Historic home, near Metro North

1st floor studio apartment in a private home. Located in the historic Mt Carmel/Little Italy section of Poughkeepsie. 5 minute walk to Metro North train station and entrance to the Walkway over the Hudson. Many restaurants, coffee/pastry shops within walking distance. There is off street parking and a lovely yard in back. Convenient to Marist College, Vassar College, the CIA, FDR home , Vanderbilt Mansion, Locust Grove, breweries, Rail trails and Wineries. NO third party booking allowed.

Guest favourite
Apartment in Newburgh
4.89 out of 5 average rating, 239 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Guest favourite
Apartment in Poughkeepsie
4.92 out of 5 average rating, 191 reviews

Your Own Pied-a-Terre "WALKWAY OVER THE HUDSON" #1

The studio is apt. w/sleeping alcove, queen bed, full kitchenette, tiled bath & shower. Private 2nd fl. entrance; great light through two sets of French doors w/southern exposure and view of the back yard. VERY CENTRAL LOCATION. Less than 10 minutes to DCC, Marist & Vassar Colleges, Vassar Bros. Medical Center, Walkway Over The Hudson, RR Station & Hudson River Park. FDR Home and CIA are 15 minutes away. We suggest that you have a car. All the calculated distances are by driving!

Guest favourite
A kitchenette area is displayed featuring a small electric kettle, a toaster oven, and a two-burner hot plate on a wooden countertop. White cabinetry with a rustic finish adds character. Natural light enters through a window, providing a glimpse of the greenery outside.
Guest suite in New Paltz
4.89 out of 5 average rating, 172 reviews

Newly built apartment steps from Mohonk preserve.

Nestled amongst the trees below Bonticou Crag this is a great base camp for climbing, hiking and biking. Five minutes from New Paltz; I do recommend having a car to access the area. Shared yard and fire pit right outside. My family and I live in the main part of the house. The outside area and house are still under construction, I’m working on it but its not put together yet. The apartment and inside area are clean and newly built with their own mini split and air circulation.

Superhost
Apartment in Poughkeepsie
4.93 out of 5 average rating, 376 reviews

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.

Top Guest favourite
Home in Poughkeepsie
4.95 out of 5 average rating, 131 reviews

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.

Popular amenities for Poughkeepsie holiday rentals

When is the best time to visit Poughkeepsie?

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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 holiday rentals in Poughkeepsie

  • Total holiday rentals

    Explore 100 holiday rentals in Poughkeepsie

  • Nightly prices starting at

    Poughkeepsie holiday rentals start at $42 AUD per night before taxes and fees

  • Verified guest reviews

    Over 6,970 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Poughkeepsie holiday 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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