Naramata Wineries - Vacation Rentals in Poughkeepsie

Hudson Valley Farmhouse on 4 acres, pets allow From US $238
         

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10.0 (1 Review)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Fire Pit + On-Site Pond: Hudson Valley Home! From US $402
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Private 37 Acre Lake Estate On 164 Acres - 11 Br From US $9,099
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Mountain Lodge Retreat, Near New Paltz & Hikes From US $605
         

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10.0 (1 Review)
Ski Chalet
  • Air Conditioner
  • Parking
  • TV
Rose & Thorne From US $600
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hot Tub-Fire Pit-Deck-BBQ-Spacious-Hiking From US $504
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Poughkeepsie

Over 109+ Luxury Places to Stay in or Near Poughkeepsie
The Red Country Cottage From US $5,000
         

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9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View
The New Paltz Moondance Ridge From US $2,500
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Wildflower Farms, Auberge Collection From US $1,578
         

9.3 (13 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Unique Dome Home With Hot Tub & Piano, on 28 acres From US $1,350
         

9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Inness From US $1,261
         

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8.0 (25 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Poughkeepsie

Over 25+ Top-Rated Vacation Rentals with a Pool in or Near Poughkeepsie
Hampton Inn by Hilton New Paltz, NY From US $230
         

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9.1 (539 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Home2 Suites By Hilton Poughkeepsie From US $144
         

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9.1 (308 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
SpringHill Suites by Marriott Fishkill From US $281
         

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9.0 (266 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Troutbeck From US $305
         

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9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Longview Pond Lodge by AvantStay From US $659
         

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9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Heidi's Inn From US $160
         

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8.9 (582 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Homewood Suites By Hilton Poughkeepsie From US $151
         

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8.8 (294 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Residence Inn by Marriott Fishkill From US $211
         

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8.8 (70 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Poughkeepsie

Over 50+ Pet-Friendly Vacation Rentals in or Near Poughkeepsie
The Hideaway From US $187
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Dog-Friendly Fishkill Tiny House in Wine Country From US $328
         

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9.7 (3 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety
SUNDOWN BB From US $194
         

9.6 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Minnewaska Lodge From US $465
         

9.1 (215 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Brand New House with Huge Patio From US $431
         

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9.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Summit Sanctuary with EV Ready Mountain Views From US $430
         

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9.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Mid-Century DJs Dream near Rhinebeck From US $195
         

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8.9 (44 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Millbrook Country House From US $215
         

8.6 (39 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Poughkeepsie

Over 8+ Large Vacation Homes & Villas in or Near Poughkeepsie
Spacious 4BD Country Gem - Fire Pit & Chill Vibes From US $389
         

Moondance Ridge Suites From US $266
         

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8.6 (68 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
The Yuzu stunning mountain retreat with hot tub From US $664
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Jenny's Country Manor From US $147
         

7.4 (18 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Security/Safety
  • Guest Services
Elixir Spring House-Stone House From US $950
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cragswood Lodge by AvantStay From US $727
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Elixir Apartment From US $173
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Poughkeepsie

Over 26+ Wheelchair Accessible Vacation Homes in or Near Poughkeepsie
Sam’s Cottage on the Greens From US $157
         

New
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
The Heartwood From US $250
         

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9.4 (192 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Inn at Bellefield Residence Inn by Marriott From US $329
         

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9.2 (206 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Mirbeau Inn & Spa, Rhinebeck From US $626
         

Americas Best Value Inn New Paltz From US $183
         

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8.6 (850 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Comfort Suites Fishkill near Interstate 84 From US $198
         

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8.6 (432 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn & Suites Poughkeepsie From US $195
         

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8.6 (231 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday Inn Express Poughkeepsie by IHG From US $201
         

8.5 (463 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Poughkeepsie Vacation Rentals and Airbnb Places to Stay Under $200

Over 32+ Poughkeepsie Vacation Rentals and Airbnb Places to Stay Under $200
Hoppy Hill Farm House From US $169
         

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9.5 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Omega Special, 1860s farm house 7 acres From US $117
         

9.0 (1 Review)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Private setting on country farm near Rhinebeck From US $134
         

7.7 (46 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Debdorkdave Hospitality Services From US $192
         

7.5 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Chic New York Studio with Kitchen From US $155
         

1.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Near Historic Sites: Bright Hyde Park Guest Suite From US $144
         

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New
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities
Pet-Friendly Staatsburg Studio - Near State Park From US $130
         

About Poughkeepsie Vacation Rentals

With more than 118 Poughkeepsie vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Naramatawineries and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Poughkeepsie.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Naramatawineries Poughkeepsie, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Poughkeepsie. Places to stay near Poughkeepsie are 1361.35 ft² on average, with prices averaging US $518 a night.

Naramatawineries makes it easy and safe to find and compare vacation rentals in Poughkeepsie with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Poughkeepsie

Type Count
Hotels 47
Vacation Homes 41
Holiday Apartments 16
B&B 6
Others 4
Ski Chalet Rentals 2
Cabin Rentals 1
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Poughkeepsie

Pro Tip: Naramatawineries makes it easy to compare the best listings on Naramatawineries homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Naramatawineries homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Poughkeepsie.

Weather in Poughkeepsie

View the weather forecast for Poughkeepsie before booking your Poughkeepsie Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Poughkeepsie Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Poughkeepsie?
How many vacation rentals are available in Poughkeepsie?

Currently, the total number of properties listed in 2026 is over 118 in the Poughkeepsie area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Poughkeepsie.