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Vacation rentals in Poughkeepsie

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Top-rated vacation rentals in Poughkeepsie

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.
Home in Rhinebeck
4.98 out of 5 average rating, 122 reviews

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.

Guest favorite
The exterior of the Little Yellow Cottage features a charming yellow facade with white trim. A round window and a cupola add character to the roof. Surrounding greenery provides a natural setting, while a small white statue of a goat sits in front of the entrance steps.
Cottage in Highland
4.89 out of 5 average rating, 682 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!

Guest favorite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
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 favorite
A bright living area is designed with a gray sectional sofa and a coffee table. A vase of fresh flowers is placed at the center. Decorative oars and a scenic image adorn the walls, while natural light streams in through the front door.
Guesthouse in Rhinebeck
4.99 out of 5 average rating, 135 reviews

Country Suite Near Omega Institute & Rhinebeck

We designed our guesthouse with the comfort seeking guest in mind. Enjoy our comfy plush beds, soft bed linens, luxurious towels, and complimentary bath amenities for your ultimate getaway. Complimentary snack and beverage selections are also provided in our efficient kitchenette (no stove) which can accommodate light meals. Our 2nd floor guesthouse offers ductless HVAC to provide the ultimate comfort AC or heating as needed. Many guests comment on our relentless pursuit of cleanliness.

Guest favorite
A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.
Cottage in New Milford
4.95 out of 5 average rating, 234 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Guest favorite
A bright bedroom features a large window dressed in sheer white curtains, allowing natural light to fill the space. A view of the outdoors is visible, highlighting trees and a wooden deck beyond the window. A spacious bed with crisp white linens is positioned near the window.
Home in Poughkeepsie
4.94 out of 5 average rating, 393 reviews

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

Top guest favorite
A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.
Home in Catskill
4.95 out of 5 average rating, 232 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Voted #3 Most Romantic AirBnB Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Top guest favorite
The exterior of a charming cottage is seen, featuring a front porch with two black chairs and potted plants. Stone steps lead up to the entrance, flanked by shrubs and trees, creating a serene setting within the landscaped grounds.
Cottage in Rhinebeck
4.93 out of 5 average rating, 181 reviews

Intimate Cottage on Private Estate

Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

Superhost
A gentle waterfall cascades over rocky terrain, surrounded by autumn foliage in varying shades. The water flows into a clear pool, with smooth stones lining the edges. Tall trees in the background create a lush, green canopy, while fallen leaves blanket the ground.
Cabin in Rhinebeck
4.88 out of 5 average rating, 426 reviews

Sunset Bungalow-Mt views on 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, and comfortable bedroom- learn more at cascadafarm.com

Top guest favorite
A landscaped backyard is visible, featuring a stone pathway leading to a seating area with a patio table and an umbrella. Vibrant flowers and greenery surround the space, creating a tranquil outdoor environment with diverse foliage and decorative elements.
Guest suite in Poughkeepsie
4.96 out of 5 average rating, 142 reviews

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.

Top guest favorite
Guest suite in Hyde Park
4.98 out of 5 average rating, 242 reviews

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.

Guest favorite
A fully equipped kitchen features modern cabinetry and stainless-steel appliances. A gas stove and built-in microwave are visible, along with a coffee maker. The countertop is complemented by a stylish backsplash in neutral tones. An adjacent dining area provides seating for four.
Home in Hyde Park
4.89 out of 5 average rating, 566 reviews

Cozy ranch near FDR Historical Site

My warm & inviting ranch home has a true homey feeling. It comfortably accommodate 4 people (please unreported guest will be charged extra $15 per person per night just be honest about it); located in heart of Hyde Park. Just mins to Culinary Institute of America and Marist College; perfect for parents attending graduations or orientations , FDR Presidential Library, Vanderbilt Mansion and Walkway over the Hudson all within mins away.

Popular amenities for Poughkeepsie vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Poughkeepsie's top sights

Walkway Over the Hudson State Historic Park

822 locals recommend

Adams Fairacre Farms

387 locals recommend

Mill House Brewing Company

183 locals recommend

Vassar College

82 locals recommend

Mid Hudson Children's Museum

85 locals recommend

Locust Grove Estate

68 locals recommend

Other great vacation rentals in Poughkeepsie

Superhost
The living room features a variety of seating options including a blue accent chair, a brown sofa, and woven armchair. A coffee table rests on a patterned rug, while natural light filters through sheer curtains, illuminating the space. A television is positioned on an antique cabinet.
Apartment in Poughkeepsie
4.93 out of 5 average rating, 376 reviews

3 Bdrm. Near Hudson Valley Colleges & Attractions

Top guest favorite
A charming cottage exterior is showcased, featuring natural wood siding and large windows. Lush greenery surrounds the building, with vibrant flowering shrubs in pink and red blooming nearby. A welcoming porch with a purple door offers a glimpse of the inviting ambiance that awaits inside.
Cottage in Clintondale
4.97 out of 5 average rating, 368 reviews

Old Mill Cottage - Upstate Mountain Views

Top guest favorite
A charming two-story house features warm wooden siding and multiple red window accents. A welcoming front porch is adorned with lights, complemented by a gently sloped pathway leading up to the entrance, surrounded by lush greenery and seasonal foliage.
Home in New Paltz
4.96 out of 5 average rating, 280 reviews

Eclectic one-bedroom house

Top guest favorite
The front of the cabin is showcased with a welcoming door decorated with a wreath. Two blue chairs and one white chair are positioned on either side, complemented by a small table and potted flowers near the entrance. Lush greenery surrounds the cabin.
Tiny home in Newburgh
4.96 out of 5 average rating, 302 reviews

Cabin in the heart of the Hudson Valley, Cabin 3

Top guest favorite
A charming cabin is nestled among vibrant trees displaying autumn foliage. A wooden staircase leads to the entrance, flanked by natural stone walls. Outdoor seating arrangements are visible on the deck, offering a peaceful retreat in a wooded setting.
Cabin in Fishkill
4.96 out of 5 average rating, 126 reviews

Secluded Hilltop Cabin near Beacon & Cold Spring

Top guest favorite
The exterior of the cottage is framed by lush green grass and features two wooden loungers. Colorful flower beds and shrubs add natural beauty, while the rustic wooden facade complements the tranquil surroundings. Large windows invite light into the cozy interior.
Cottage in Woodstock
4.95 out of 5 average rating, 450 reviews

Woodstock Mountain Cottage

Top guest favorite
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, 355 reviews

Spacious and stylish entire one bedroom apartment.

Guest favorite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 427 reviews

The Cove Cabin

When is the best time to visit Poughkeepsie?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$19,864 GYDG$24,046 GYDG$24,464 GYDG$24,046 GYDG$27,392 GYDG$28,228 GYDG$27,601 GYDG$28,646 GYDG$26,764 GYDG$29,273 GYDG$27,601 GYDG$26,764 GYD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°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 G$6,273 GYD 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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