Short-Term Rentals in Oakland Beach, NY: Compare 10+ Sites & Save

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166 Best Short-Term Rentals in Oakland Beach (Starting from $122)

Spacious 3 bedroom house 45mins to NYC great hotel alternative for big group
Spacious 3 bedroom house 45mins to NYC great hotel alternative for big group
House
Port Chester, NY, USA
2.7k from Oakland Beach center

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

3 Bedrooms11 Guests
New to Booking
$466
Average price / night
Check Availability
Flex Comfort Apts of Westchester #2
Flex Comfort Apts of Westchester #2
Apartment
Rye Brook, NY, 10573, United States
2.0k from Oakland Beach center

AC, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

2 Bedrooms4 Guests
9.4

Superb

31 reviews

$145
Average price / night
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Charming Victorian Home in the Heart of White Plains
Charming Victorian Home in the Heart of White Plains
Apartment
White Plains, NY, USA
5.2k from Oakland Beach center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$141
Average price / night
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Flex Comfort Apts of Westchester #1
Flex Comfort Apts of Westchester #1
Apartment
Rye Brook, NY, 10573, United States
2.0k from Oakland Beach center

AC, Balcony, Barbecue, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.8

Exceptional

40 reviews

$213
Average price / night
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Luxury Apartments by Hyatus White Plains
Luxury Apartments by Hyatus White Plains
Apartment
White Plains, NY, USA
5.6k from Oakland Beach center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Serviced apartments, Pet-friendly, Lodgings

10 Bedrooms9 Guests
8.0

Good

1 reviews

$9500
Average price / night
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Charming 1-bedroom apartment in perfect Port Chester with AC, WiFi
Charming 1-bedroom apartment in perfect Port Chester with AC, WiFi
Apartment
Port Chester, NY, 10573, United States
2.6k from Oakland Beach center

AC, Heater, Internet, Kitchen, Laundry, No Smoking, TV, Washer

1 Bedroom2 Guests
8.8

Fabulous

5 reviews

$186
Average price / night
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Best hotel alternative for big group near train to NYC
Best hotel alternative for big group near train to NYC
House
Greenwich, CT, USA
6.3k from Oakland Beach center

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

4 Bedrooms8 Guests
New to Booking
$749
Average price / night
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Brand New 5 min from downtown Rye & Train NYC Vibe Pet Friendly Hot List!!
Brand New 5 min from downtown Rye & Train NYC Vibe Pet Friendly Hot List!!
House
Rye, NY, 10580, United States
2.6k from Oakland Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1503
Average price / night
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Global Luxury Suites Downtown White Plains
Global Luxury Suites Downtown White Plains
Apartment
White Plains, NY, USA
6.4k from Oakland Beach center

Apartments, Accommodations, Pools, Parking, 4-star, Lodgings, Vacation rentals, Places to stay, Family

16 Bedrooms11 Guests
6.9

Good

48 reviews

$268
Average price / night
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Closest VRBO to Capitol Theater in Portchester, NY
Closest VRBO to Capitol Theater in Portchester, NY
Condo
Port Chester, NY, 10573, United States
2.7k from Oakland Beach center

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

2 Bedrooms3 Guests
9.8

Exceptional

25 reviews

$400
Average price / night
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Modern Apt with Kitchen and Gym
Modern Apt with Kitchen and Gym
Apartment
White Plains, NY, USA
6.5k from Oakland Beach center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

2 Bedrooms5 Guests
New to Booking
$231
Average price / night
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3br + game rm abt 45min drive or easy train to NYC
3br + game rm abt 45min drive or easy train to NYC
House
Port Chester, NY, 10573, United States
2.7k from Oakland Beach center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms11 Guests
10.0

Exceptional

2 reviews

$640
Average price / night
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Modern Apt Near Downtown
Modern Apt Near Downtown
Apartment
White Plains, NY, USA
6.5k from Oakland Beach center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom3 Guests
New to Booking
$204
Average price / night
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House in quiet Westchester county neighborhood
House in quiet Westchester county neighborhood
House
Port Chester, NY, 10573, United States
2.7k from Oakland Beach center

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

4 Bedrooms10 Guests
New to Booking
$868
Average price / night
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Cozy Homeva Chatterton WP
Cozy Homeva Chatterton WP
House
White Plains, NY, USA
6.8k from Oakland Beach center

Kitchen, View, Laundry, Internet, Balcony/Terrace, Entertainment, Guest Services

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$138
Average price / night
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The All Seasons Oasis! Entire home. Pool is Open Thru Sept!
The All Seasons Oasis! Entire home. Pool is Open Thru Sept!
House
Port Chester, NY, 10573, United States
2.8k from Oakland Beach center

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

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$2246
Average price / night
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Balcony Room At Cozy Homeva
Balcony Room At Cozy Homeva
House
White Plains, NY, USA
6.8k from Oakland Beach center

Air Conditioner, Entertainment, View, Balcony/Terrace, Kitchen, Fireplace/Heating, Tv

1 Bedroom2 Guests
New to Booking
$122
Average price / night
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Modern & Cozy 1 bdrm Apt near NYC, GREENWICH , RYE / Sleeps 4
Modern & Cozy 1 bdrm Apt near NYC, GREENWICH , RYE / Sleeps 4
Apartment
Port Chester, NY, 10573, United States
3.0k from Oakland Beach center

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

1 Bedroom5 Guests
New to Booking
$237
Average price / night
Check Availability
Double Room At Cozy Homeva
Double Room At Cozy Homeva
House
White Plains, NY, USA
6.8k from Oakland Beach center

Laundry, Fireplace/Heating, Air Conditioner, Entertainment, Kitchen, Balcony/Terrace, Security/Safety

1 Bedroom4 Guests
New to Booking
$156
Average price / night
Check Availability
Warm & Modern 1-Bedroom Retreat Near NYC, Greenwich & Rye, Sleeps 4
Warm & Modern 1-Bedroom Retreat Near NYC, Greenwich & Rye, Sleeps 4
Apartment
Port Chester, NY, 10573, United States
3.1k from Oakland Beach center

AC, Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space, TV

1 Bedroom4 Guests
New to Booking
$265
Average price / night
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Cozy Homeva Battle Hill WP
Cozy Homeva Battle Hill WP
House
White Plains, NY, USA
6.8k from Oakland Beach center

Cheap, Accommodations, Homestays, Lodgings, Places to stay, Self-catering

4 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$171
Average price / night
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Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Apartment
Port Chester, NY, 10573, United States
3.5k from Oakland Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

30 reviews

$412
Average price / night
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Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
Cottage
Greenwich, CT, 06831, United States
3.5k from Oakland Beach center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

2 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$770
Average price / night
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Turnkey Home in Prime Rye
Turnkey Home in Prime Rye
House
Rye, NY, 10580, United States
3.7k from Oakland Beach center

AC, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, No Smoking, TV

4 Bedrooms8 Guests
New to Booking
$486
Average price / night
Check Availability
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Apartment
Greenwich, CT, 06831, United States
3.7k from Oakland Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Microwave, No Smoking, Patio

1 Bedroom3 Guests
2.0

Review score

1 reviews

$370
Average price / night
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Rye Colonial Walk to Town & Bike to Beach
Rye Colonial Walk to Town & Bike to Beach
House
Rye, NY, 10580, United States
3.7k from Oakland Beach center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$984
Average price / night
Check Availability
Modern Apartment 5 min from train/beach Greenwich
Modern Apartment 5 min from train/beach Greenwich
Condo
Greenwich, CT, 06830, United States
3.8k from Oakland Beach center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$690
Average price / night
Check Availability

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 Short-Term Rentals in Oakland Beach.

Where to stay in Oakland Beach? Best neighborhoods & areas

Oakland Beach Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 166 verified short-term rentals in Oakland Beach, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Oakland Beach vary depending on location, property size, and travel dates. Rates typically start from around $122 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Oakland Beach include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Oakland Beach, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Oakland Beach often include amenities such as Fireplace/Heating, Kitchen, and Wellness Facilities, providing a comfortable and convenient stay.

Short-term rentals in Oakland Beach are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.