45+ Vacation Rentals Near Pleasant Square |
  1. USA
  2. New York
  3. White Plains
  4. Pleasant Square

Rent The Cottages - Vacation Rentals in Pleasant Square

Neighbor's house - Welcome! From US $198
         

10.0 (5 Reviews)
House
Neighbor's house - Welcome!
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Hudson River Views Briarcliff Manor Home with Deck From US $1,143
         

|
10.0 (2 Reviews)
House
Hudson River Views Briarcliff Manor Home with Deck
  • Parking
  • Pet Friendly
  • Accessibility

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Foliage at Westchester Manor - Near Sleepy Hollow From US $865
         

New
House
Foliage at Westchester Manor - Near Sleepy Hollow
  • Parking
  • Pool
  • Balcony/Terrace

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Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven From US $270
         

9.8 (16 Reviews)
Cottage
Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Ossining Vacation Rental Near River, Trails and MTA! From US $600
         

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8.7 (3 Reviews)
House
Ossining Vacation Rental Near River, Trails and MTA!
  • Parking
  • Pet Friendly
  • View

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Ossining Vacation Rental Near River, Trails & Mta! From US $711
         

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New
Cottage
Ossining Vacation Rental Near River, Trails & Mta!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hudson River Views: Briarcliff Manor Home w/Deck From US $942
         

9.8 (12 Reviews)
House
Hudson River Views: Briarcliff Manor Home w/Deck
  • Air Conditioner
  • Parking
  • Pet Friendly

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Windrose on Hudson From US $214
         

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7.3 (41 Reviews)
Hotel
Windrose on Hudson
  • Air Conditioner
  • Parking
  • View

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Windrose On Hudson From US $230
         

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8.2 (106 Reviews)
Hotel
Windrose On Hudson
  • Air Conditioner
  • Parking
  • TV

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Ossining Vacation Rental Near River, Trails & MTA! From US $415
         

8.0 (13 Reviews)
House
Ossining Vacation Rental Near River, Trails & MTA!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven" From US $426
         

10.0 (11 Reviews)
House
Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven"
  • Air Conditioner
  • Parking
  • Pool

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Cozy house on the Hudson From US $269
         

9.6 (68 Reviews)
House
Cozy house on the Hudson
  • Air Conditioner
  • Parking
  • TV

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EXTENDED STAY FOR PROFESSIONALS - Private Studio Apartment From US $128
         

New
Apartment
EXTENDED STAY FOR PROFESSIONALS - Private Studio Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

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4 Comfortable Double Rooms | Close to Waterfront Music, Events & Breweries
New
From US $1,186
         

New
Hotel
4 Comfortable Double Rooms | Close to Waterfront Music, Events & Breweries
  • Air Conditioner
  • Parking
  • Pool

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Relax in 4 Double Guestrooms Near Warren Street Shops & Waterfront Parks
New
From US $1,186
         

New
Hotel
Relax in 4 Double Guestrooms Near Warren Street Shops & Waterfront Parks
  • Air Conditioner
  • Parking
  • Pool

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Relax in 4 Double Guestrooms Near Warren Street Shops & Waterfront Parks
New
From US $1,186
         

New
Hotel
Relax in 4 Double Guestrooms Near Warren Street Shops & Waterfront Parks
  • Air Conditioner
  • Parking
  • Pool

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4 Comfortable Double Rooms | Close to Waterfront Music, Events & Breweries
New
From US $1,186
         

New
Hotel
4 Comfortable Double Rooms | Close to Waterfront Music, Events & Breweries
  • Air Conditioner
  • Parking
  • Pool

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Close to Art Studios & Hudson Nightlife | 3 Inviting Double Guestrooms
New
From US $975
         

New
Hotel
Close to Art Studios & Hudson Nightlife | 3 Inviting Double Guestrooms
  • Air Conditioner
  • Parking
  • Pool

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Close to Art Studios & Hudson Nightlife | 3 Inviting Double Guestrooms
New
From US $888
         

New
Hotel
Close to Art Studios & Hudson Nightlife | 3 Inviting Double Guestrooms
  • Air Conditioner
  • Parking
  • Pool

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Close to Historic Sites, Markets & Local Wineries | 3 Comfortable Double Rooms
New
From US $888
         

New
Hotel
Close to Historic Sites, Markets & Local Wineries | 3 Comfortable Double Rooms
  • Air Conditioner
  • Parking
  • Pool

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Close to Historic Sites, Markets & Local Wineries | 3 Comfortable Double Rooms
New
From US $874
         

New
Hotel
Close to Historic Sites, Markets & Local Wineries | 3 Comfortable Double Rooms
  • Air Conditioner
  • Parking
  • Pool

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2 Bright Double Rooms | Near Local Dining and Shopping at Palisades Center
New
From US $654
         

New
Hotel
2 Bright Double Rooms | Near Local Dining and Shopping at Palisades Center
  • Air Conditioner
  • Parking
  • Pool

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2 Comfortable Double Rooms | Near Historic Sites, Markets & Local Wineries
New
From US $591
         

New
Hotel
2 Comfortable Double Rooms | Near Historic Sites, Markets & Local Wineries
  • Air Conditioner
  • Parking
  • Pool

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2 Bright Double Rooms | Near Local Dining and Shopping at Palisades Center
New
From US $591
         

New
Hotel
2 Bright Double Rooms | Near Local Dining and Shopping at Palisades Center
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Rentthecottages makes it easy to compare the best listings on Rentthecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Rentthecottages 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 Pleasant Square.

Weather in Pleasant Square

View the weather forecast for Pleasant Square before booking your Pleasant Square 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

Top Attractions Around Pleasant Square, NY

Rentthecottages offers a large selection of top attractions around Pleasant Square. Research things to do on your vacation before you visit Pleasant Square.


Bear Mountain State Park Palisades Center Westchester County Center Purchase College Westchester Broadway Theatre Tarrytown Music Hall The Westchester Mall Nyack College Harriman State Park Governor Mario M. Cuomo Bridge Manhattanville College Lyndhurst Mansion Galleria at White Plains Pace University Law School Sleepy Hollow Cemetery Rockland Community College Tarrytown Lighthouse Pierson Park Doral Arrowwood Golf Club Van Cortlandt Manor