Antigua Cottages - Vacation Rentals in Pleasantville

Hudson River Views: Briarcliff Manor Home w/Deck From US $1,361
         

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10.0 (2 Reviews)
House
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  • Pet Friendly
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Luxury NY Home with Free Parking From US $381
         

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8.0 (1 Review)
House
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Neighbor's house - Welcome! From US $198
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Cozy 1BR/2 Queen Beds/Free Parking/Private Stay From US $814
         

10.0 (1 Review)
Apartment
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  • Pet Friendly
Modern 1BR Apt/Free Parking/Near NYC From US $782
         

10.0 (1 Review)
House
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  • Parking
  • Pet Friendly
Lovely house in Tarrytown From US $437
         

10.0 (1 Review)
House
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  • Parking
  • Pet Friendly
Stylish Tarrytown Studio - Walk to Train & Main St From US $345
         

Hudson River Views: Briarcliff Manor Home w/Deck From US $1,493
         

9.8 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Pleasantville

Over 152+ Luxury Places to Stay in or Near Pleasantville
2BDRM COTTAGE IN PLEASANTVILLE From US $3,564
         

New
Cottage
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Spectacular Mansion with pool/spa - close to NYC From US $2,157
         

Luxury NYC Retreat with Free Parking From US $1,604
         

8.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Luxury Urban Retreat + Spacious & Stylish From US $1,436
         

New
Apartment
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  • Pet Friendly
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Top-Rated Vacation Rentals with a Pool in Pleasantville

Over 43+ Top-Rated Vacation Rentals with a Pool in or Near Pleasantville
Castle Retreat w/Pool, BBQ, Game Room & Pets OK! From US $1,324
         

9.2 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Baymont by Wyndham White Plains - Elmsford From US $160
         

8.4 (1692 Reviews)
Hotel
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  • Parking
  • Pool
Sheraton Tarrytown Hotel From US $174
         

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8.4 (1000 Reviews)
Hotel
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  • Parking
  • Pool
Sheraton Tarrytown Hotel From US $159
         

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8.0 (263 Reviews)
Hotel
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  • Parking
  • Pet Friendly
Baymont by Wyndham White Plains - Elmsford From US $159
         

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7.9 (1332 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Tarrytown House Estate From US $140
         

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7.8 (842 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Pleasantville

Over 55+ Pet-Friendly Vacation Rentals in or Near Pleasantville
NYC-Area Escape Near River, Trails & MTA! From US $689
         

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8.7 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • View
3BR Prime Luxury NY - Free Parking From US $1,263
         

6.0 (1 Review)
Apartment
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  • Pet Friendly
  • Security/Safety
NYC-Area Escape Near River, Trails & MTA! From US $659
         

8.2 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW! Cozy Pleasantville Retreat Unit 2 From US $346
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Pleasantville

Over 30+ Large Vacation Homes & Villas in or Near Pleasantville
3 Mi to Downtown: Spacious White Plains Home From US $768
         

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8.0 (4 Reviews)
House
  • Parking
  • View
  • Security/Safety
Luxury NYC Home Game Room Free Parking From US $778
         

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4.0 (1 Review)
Villa
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  • Pet Friendly
3 Mi to Downtown: Spacious White Plains Home From US $655
         

9.2 (15 Reviews)
House
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  • Parking
  • Balcony/Terrace
Stylish 3BR Home Game Room Free Parking Sleeps 16 From US $1,172
         

New
House
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  • Pet Friendly
  • Security/Safety

Wheelchair Accessible Vacation Homes in Pleasantville

Over 36+ Wheelchair Accessible Vacation Homes in or Near Pleasantville
Courtyard by Marriott Tarrytown Westchester County From US $328
         

Courtyard by Marriott Tarrytown Westchester County From US $184
         

Pleasantville Vacation Rentals and Airbnb Places to Stay Under $200

Over 25+ Pleasantville Vacation Rentals and Airbnb Places to Stay Under $200
American Room At Cozy Homeva From US $104
         

Cozy tiny log cabin on 14 acres From US $199
         

9.6 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Amazing Large Private Studio!+ From US $170
         

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

Instantly Bookable Vacation Homes in Pleasantville

Over 43+ Instantly Bookable Vacation Homes in or Near Pleasantville
Polished 1BR w/Accessible Room Features + Sauna From US $515
         

Near NYC! | Stylish Guestroom From US $392
         

Adorable 2-bedroom bed & breakfast in fantastic Ossining location From US $251
         

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Bed & Breakfast
  • Air Conditioner
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  • Bedding/Linens

About Pleasantville Vacation Rentals

With more than 161 Pleasantville vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Antiguacottages 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 Pleasantville.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Antiguacottages Pleasantville, 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 Pleasantville. Places to stay near Pleasantville are 852.24 ft² on average, with prices averaging US $645 a night.

Antiguacottages makes it easy and safe to find and compare vacation rentals in Pleasantville 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 Pleasantville

Type Count
Vacation Homes 68
Hotels 49
Holiday Apartments 32
Cottages 4
Villas 3
B&B 2
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Pleasantville

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

Weather in Pleasantville

View the weather forecast for Pleasantville before booking your Pleasantville 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

Pleasantville Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 161 in the Pleasantville area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pleasantville.