Vacation Rentals in Pleasant Valley, NY: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  New York

  5.  Poughkeepsie
  6.  Pleasant Valley

Refine your search

Price per night

Amenity Filter

Rating

35 Best Vacation Rentals in Pleasant Valley (Starting from $108)

Near Marist/Vassar/Culinary Inst./Historic Sites!
Near Marist/Vassar/Culinary Inst./Historic Sites!
House
Pleasant Valley, NY, USA
3.3k from Pleasant Valley center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms4 Guests
9.5

Superb

2 reviews

$449
Average price / night
Check Availability
 Converted Barn, Estate Setting ,  & Pool in Hudson Valley near Millbrook
Converted Barn, Estate Setting , & Pool in Hudson Valley near Millbrook
House
Pleasant Valley, NY, 12569, United States
1.5k from Pleasant Valley center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$865
Average price / night
Check Availability
Debdorkdave Hospitality Services
Debdorkdave Hospitality Services
House
Poughkeepsie, NY, USA
5.4k from Pleasant Valley center

Cheap, Accommodations, Parking, Homestays, Lodgings, Vacation rentals, Places to stay

3 Bedrooms3 Guests
7.5

Good

10 reviews

$192
Average price / night
Check Availability
Bucolic Federalist Home Near Millbrook New York
Bucolic Federalist Home Near Millbrook New York
House
Pleasant Valley, NY, 12569, United States
1.6k from Pleasant Valley center

Dryer, Fireplace, Internet, Laundry, No Smoking, Pool, Toys, TV, Washer

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$453
Average price / night
Check Availability
Beautiful home with mountain top views with an EV and NEMA connection!
Beautiful home with mountain top views with an EV and NEMA connection!
House
Poughkeepsie, NY, USA
7.2k from Pleasant Valley center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$306
Average price / night
Check Availability
Studio near Millbrook, Poughkeepsie.
Studio near Millbrook, Poughkeepsie.
Apartment
Pleasant Valley, NY, 12569, United States
2.0k from Pleasant Valley center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio

1 Bedroom3 Guests
9.2

Superb

48 reviews

$139
Average price / night
Check Availability
Hudson Valley Horse Farm Retreat in Salt Point
Hudson Valley Horse Farm Retreat in Salt Point
House
Salt Point, NY, USA
7.8k from Pleasant Valley center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$295
Average price / night
Check Availability
Pleasant Valley Pines
Pleasant Valley Pines
House
Pleasant Valley, NY, 12569, United States
3.2k from Pleasant Valley center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
8.0

Good

2 reviews

$649
Average price / night
Check Availability
HV Spacious Retreat sleeps 13 with pool and hot tub
HV Spacious Retreat sleeps 13 with pool and hot tub
House
Poughkeepsie, NY, USA
9.7k from Pleasant Valley center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

4 Bedrooms13 Guests
New to Booking
$935
Average price / night
Check Availability
Private Hudson Valley Home Near Wine Trail / Antiquing / Orchards
Private Hudson Valley Home Near Wine Trail / Antiquing / Orchards
House
Pleasant Valley, NY, 12569, United States
3.3k from Pleasant Valley center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms4 Guests
New to Booking
$141
Average price / night
Check Availability
Wappinger Cottage - Scandinavian retreat on a creek
Wappinger Cottage - Scandinavian retreat on a creek
Cottage
Poughkeepsie, NY, 12603, United States
4.5k from Pleasant Valley center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

30 reviews

$652
Average price / night
Check Availability
Modern Getaway Retreat House on 2 Acres
Modern Getaway Retreat House on 2 Acres
House
Poughkeepsie, NY, 12601, United States
4.8k from Pleasant Valley center

AC, Heater, Internet

3 Bedrooms8 Guests
7.0

Good

2 reviews

$429
Average price / night
Check Availability
Apartment in scenic Hudson Valley New York
Apartment in scenic Hudson Valley New York
Apartment
Verbank, NY, 12585, United States
5.5k from Pleasant Valley center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom3 Guests
10.0

Exceptional

39 reviews

$108
Average price / night
Check Availability
Hidden Charm in Hudson Valley In Dutchess County
Hidden Charm in Hudson Valley In Dutchess County
House
Salt Point, NY, 12578, United States
6.0k from Pleasant Valley center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms11 Guests
10.0

Exceptional

28 reviews

$605
Average price / night
Check Availability
Waterfall Sound & Beach-Inspired Country Wing
Waterfall Sound & Beach-Inspired Country Wing
Cottage
Verbank, NY, 12585, United States
6.2k from Pleasant Valley center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms5 Guests
10.0

Exceptional

7 reviews

$274
Average price / night
Check Availability
ESKape Manor: Great Views, Hot Tub & Fun Amenities
ESKape Manor: Great Views, Hot Tub & Fun Amenities
Cabin
Lagrangeville, NY, 12540, United States
6.5k from Pleasant Valley center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
New to Booking
$640
Average price / night
Check Availability
Summit Sanctuary: EV Ready Mountain Views
Summit Sanctuary: EV Ready Mountain Views
House
Poughkeepsie, NY, 12601, United States
7.2k from Pleasant Valley center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
9.0

Fabulous

14 reviews

$414
Average price / night
Check Availability
Modern Converted Barn with Hot Tub!
Modern Converted Barn with Hot Tub!
House
Hyde Park, NY, 12538, United States
7.3k from Pleasant Valley center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$945
Average price / night
Check Availability
Pet-friendly Cottage at Historic Millbrook Farm Estate
Pet-friendly Cottage at Historic Millbrook Farm Estate
Cottage
Millbrook, NY, 12545, United States
7.3k from Pleasant Valley center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms5 Guests
9.2

Superb

14 reviews

$272
Average price / night
Check Availability
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
House
Poughkeepsie, NY, 12603, United States
7.4k from Pleasant Valley center

AC, Balcony, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$426
Average price / night
Check Availability
Collins Estate East Wing Efficiency 2 bed 2 bath, AC, in Lagrangeville, NY
Collins Estate East Wing Efficiency 2 bed 2 bath, AC, in Lagrangeville, NY
Apartment
Lagrangeville, NY, 12540, United States
7.9k from Pleasant Valley center

AC, Free Parking, Heater, Internet, No Smoking, TV

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$333
Average price / night
Check Availability
Fabulous 2-bedroom Creekside cottage on the historic Collins Estate.
Fabulous 2-bedroom Creekside cottage on the historic Collins Estate.
Cottage
Lagrangeville, NY, 12540, United States
8.0k from Pleasant Valley center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
New to Booking
$278
Average price / night
Check Availability
Timeless Three-Story Treasure w/ Pool, Rolling Hills and Fireplace
Timeless Three-Story Treasure w/ Pool, Rolling Hills and Fireplace
House
Lagrangeville, NY, 12540, United States
8.2k from Pleasant Valley center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$732
Average price / night
Check Availability
Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC
Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC
House
Salt Point, NY, 12578, United States
8.2k from Pleasant Valley center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.6

Exceptional

14 reviews

$914
Average price / night
Check Availability
Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20)
Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20)
Villa
Hyde Park, NY, 12538, United States
8.9k from Pleasant Valley center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

8 Bedrooms20 Guests
9.6

Exceptional

19 reviews

$2067
Average price / night
Check Availability
Enjoy pool time at our spacious home; minutes from the village of Millbrook!
Enjoy pool time at our spacious home; minutes from the village of Millbrook!
House
Millbrook, NY, 12545, United States
9.2k from Pleasant Valley center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

60 reviews

$480
Average price / night
Check Availability
Stunning Light-Filled Contemporary Home on 7 Acres
Stunning Light-Filled Contemporary Home on 7 Acres
House
Salt Point, NY, 12578, United States
9.2k from Pleasant Valley center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms6 Guests
10.0

Exceptional

27 reviews

$690
Average price / night
Check Availability

Other accommodation types in Pleasant Valley:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Pleasant Valley.

Pleasant Valley Vacation Rentals on the Map

Frequently Asked Questions

You can explore 35 verified vacation rentals in Pleasant Valley. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Pleasant Valley vary depending on the season, property size, and location. Rates typically start from around $108 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Pleasant Valley include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Pleasant Valley welcome pets. Currently, 18 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Pleasant Valley often include amenities such as Fireplace/Heating, Bedding/Linens, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.