55+ Vacation Rentals Near Oakland Beach |
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  2. New York
  3. White Plains
  4. Oakland Beach

Book the Best Places to Stay in Oakland Beach

Find Curated Vacation Rentals, Boutique Cabins, and Stylish Eco-Friendly Acommodation in Oakland Beach

Quaint duplex with private yard. Walk to beach, dining, & shopping! From US $350
         

10.0 (47 Reviews)
House
Quaint duplex with private yard. Walk to beach, dining, & shopping!
  • Air Conditioner
  • Parking
  • Pet Friendly

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2 Mi to NYC Train: WFH-Friendly Greenwich Apt! From US $300
         

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3.0 (1 Review)
Apartment
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
  • Parking
  • Pet Friendly
  • Balcony/Terrace

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2 Mi to NYC Train: Wfh-friendly Greenwich Apt! From US $440
         

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New
Apartment
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Flex Comfort Apts of Westchester #1 From US $390
         

10.0 (41 Reviews)
Apartment
Flex Comfort Apts of Westchester #1
  • Air Conditioner
  • TV
  • View

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Cozy Riverfront Cottage - Pool, Hot Tub, 35 min NYC From US $556
         

New
House
Cozy Riverfront Cottage - Pool, Hot Tub, 35 min NYC
  • Air Conditioner
  • Parking
  • Pool

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Courtyard by Marriott Rye From US $382
         

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8.6 (1002 Reviews)
Hotel
Courtyard by Marriott Rye
  • Air Conditioner
  • Parking
  • TV

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Cozy Stay Near Capitol Theatre/Downtown — Very Walkable! From US $419
         

10.0 (31 Reviews)
Apartment
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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Hyatt House White Plains From US $236
         

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8.1 (491 Reviews)
Hotel
Hyatt House White Plains
  • Air Conditioner
  • Parking
  • Pet Friendly

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Entire 2 Bed-room Roomy Apartment ~ 1 min to Train for NYC From US $199
         

6.8 (5 Reviews)
Apartment
Entire 2 Bed-room Roomy Apartment ~ 1 min to Train for NYC
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Riverfront Cottage w/Heated Pool, Hot Tub & Fireplace, 35 min to NYC From US $871
         

10.0 (7 Reviews)
Cottage
Riverfront Cottage w/Heated Pool, Hot Tub & Fireplace, 35 min to NYC
  • Air Conditioner
  • Parking
  • Pet Friendly

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Rye Colonial Walk to Town & Bike to Beach From US $760
         

10.0 (5 Reviews)
House
Rye Colonial Walk to Town & Bike to Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tranquil modern upstairs apt. Walk to restaurants & beach! Off-street parking, From US $271
         

10.0 (3 Reviews)
Apartment
Tranquil modern upstairs apt. Walk to restaurants & beach! Off-street parking,
  • Air Conditioner
  • Pet Friendly
  • TV

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Best Location in Rye-5 min walk to Town and Metro North Train From US $923
         

10.0 (1 Review)
House
Best Location in Rye-5 min walk to Town and Metro North Train
  • Air Conditioner
  • Parking
  • TV

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Cozy 2br apartment in Greenwich with driveway. Walk to restaurants & beach! From US $297
         

10.0 (1 Review)
Apartment
Cozy 2br apartment in Greenwich with driveway. Walk to restaurants & beach!
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area

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Charming duplex with private yard. Close to the beach, dining & shopping! From US $296
         

9.8 (40 Reviews)
House
Charming duplex with private yard. Close to the beach, dining & shopping!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Flex Comfort Apts of Greenwich #3 From US $259
         

9.4 (64 Reviews)
Apartment
Flex Comfort Apts of Greenwich #3
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Flex Comfort Apts of Westchester #2 From US $214
         

9.4 (31 Reviews)
Apartment
Flex Comfort Apts of Westchester #2
  • Air Conditioner
  • TV
  • Security/Safety

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Flex Comfort Apts of Greenwich #2 From US $195
         

9.2 (59 Reviews)
Apartment
Flex Comfort Apts of Greenwich #2
  • Air Conditioner
  • TV
  • View

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Spacious 3b/3b Mediterranean in White Plains From US $619
         

9.2 (16 Reviews)
House
Spacious 3b/3b Mediterranean in White Plains
  • Air Conditioner
  • Parking
  • TV

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Flex Comfort Apts of Greenwich #1 From US $163
         

9.0 (27 Reviews)
Apartment
Flex Comfort Apts of Greenwich #1
  • Air Conditioner
  • TV
  • View

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Charming 1-bedroom apartment in perfect Port Chester with AC, WiFi From US $187
         

8.8 (5 Reviews)
Apartment
Charming 1-bedroom apartment in perfect Port Chester with AC, WiFi
  • Air Conditioner
  • TV
  • Security/Safety

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Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich From US $268
         

7.6 (4 Reviews)
Apartment
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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2 Mi to NYC Train: WFH-Friendly Greenwich Apt! From US $264
         

2.0 (1 Review)
Apartment
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Warm & Modern 1-Bedroom Retreat Near NYC, Greenwich & Rye, Sleeps 4 From US $236
         

New
Apartment
Warm & Modern 1-Bedroom Retreat Near NYC, Greenwich & Rye, Sleeps 4
  • Air Conditioner
  • Parking
  • TV

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

Weather in Oakland Beach

View the weather forecast for Oakland Beach before booking your Oakland Beach 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 Oakland Beach, NY

Bettertrips offers a large selection of top attractions around Oakland Beach. Research things to do on your vacation before you visit Oakland Beach.


Rye Beach Capitol Theatre Empire City Casino Westchester County Center New Roc City Purchase College Rye Playland Van Cortlandt Park Westchester Broadway Theatre Tarrytown Music Hall Pelham Bay Park Yonkers Raceway The Westchester Mall Iona College Governor Mario M. Cuomo Bridge Westchester's Ridge Hill Manhattanville College Chelsea Piers Orchard Beach Legoland Discovery Center Westchester

Other Places to Stay Near Oakland Beach, NY


Rye Beach 51 Properties

Oakland Beach Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Oakland Beach?

Currently, the total number of properties listed in 2026 is over 55 in the Oakland Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Oakland Beach.