Oakland Beach Tours

Plan a trip to see Oakland Beach

Price found within the past 48 hours. Click for updated prices.
Harpoon House

Harpoon House

3 out of 5
Price was $704, price is now $341 per person
$341
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
8.4/10 Very Good! (147 reviews)
We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended.

Reviewed on Oct 20, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $1,285, price is now $605 per person
$605
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
9.2/10 Wonderful! (1,002 reviews)
I stay here often and the rooms are spacious clean and the hotel staff is very accommodating. I always have a wonderful experience and I highly recommend staying here. They also offer free breakfast and dinner which is a nice perk.

Reviewed on Nov 25, 2025

Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Price was $1,075, price is now $522 per person
$522
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to White Plains (HPN)
2/10 (1 review)

Popular places to visit

Duran Duran plays the Capitol Theatre in Port Chester, NY in support of their Paper Gods album. Here they perform "Rio" to close out the night. #duranlive

Capitol Theatre

Enjoy a show at Capitol Theatre, a theater with a story to tell in Port Chester. Discover the entertainment choices and shops in this family-friendly area.

Capitol Theatre

Rye Playland

Have a fun-filled day with the family at Rye Playland during your visit to Rye. Discover the live music in this family-friendly area, or seek out its hiking trails.

Rye Playland

Marshlands Conservancy

Explore the great outdoors at Marshlands Conservancy, a lovely green space in Rye. You can seek out the hiking trails in this family-friendly area.

Marshlands Conservancy

Jay Heritage Center

You can study the exhibits at Jay Heritage Center, a museum with a story of its own, during your travels to Rye. While in this family-friendly area, you can savor the top-notch restaurants.

Jay Heritage Center

Hawthorne Beach

Why not spend a lazy afternoon at Hawthorne Beach during your trip to Greenwich? Stroll along this romantic area's waterfront, or simply enjoy its restaurants.

Hawthorne Beach

Clay Art Center Gallery

You can study the exhibits at Clay Art Center Gallery, a museum with a story of its own, during your travels to Port Chester. Take in the entertainment choices in this family-friendly area.

Clay Art Center Gallery

Best Lodging Options Near Oakland Beach

Rye Colonial Walk to Town & Bike to Beach

Rye Colonial Walk to Town & Bike to Beach

Rye NY
Rye Colonial Walk to Town & Bike to Beach
Courtyard by Marriott Rye

Courtyard by Marriott Rye

3 out of 5
631 Midland Ave Rye Brook NY
Courtyard by Marriott Rye
Luxury Home with Amazing Water Views - Perfect for an intimate family gathering

Luxury Home with Amazing Water Views - Perfect for an intimate family gathering

Mamaroneck NY
Luxury Home with Amazing Water Views - Perfect for an intimate family gathering
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

Mamaroneck NY
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Port Chester NY
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Charming 1-bedroom apartment in perfect Port Chester with AC, WiFi

Charming 1-bedroom apartment in perfect Port Chester with AC, WiFi

Port Chester NY
Charming 1-bedroom apartment in perfect Port Chester with AC, WiFi
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2 out of 5
Mamaroneck NY
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
P21018 - 2nd St @ Mamaroneck

P21018 - 2nd St @ Mamaroneck

Mamaroneck NY
P21018 - 2nd St @ Mamaroneck
Quaint duplex with private yard. Walk to beach, dining, & shopping!

Quaint duplex with private yard. Walk to beach, dining, & shopping!

GREENWICH CT
Quaint duplex with private yard. Walk to beach, dining, & shopping!
See all 812 properties in Oakland Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.