Name: The Bentley Hotel Southampton
Price range: $259 total
Rating: 9.6

The Shoals Suites and Slips

61600 Main Rd Southold NY

$267 nightly

$302 total

May 31 - Jun 1

Total with taxes and fees

Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...

9.4/10 Exceptional! (271 reviews)

"Great a accomodation"

Reviewed on May 22, 2026

Vine & Sand

47100 New York 25 Southold NY

$415 nightly

$474 total

May 28 - May 29

Total with taxes and fees

Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux ...

9.8/10 Exceptional! (16 reviews)

"Location was perfect for visiting the wineries… breakfast was to die for!"

Reviewed on Mar 22, 2026

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

$227 nightly

$259 total

May 28 - May 29

Total with taxes and fees

Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...

9.6/10 Exceptional! (505 reviews)

"Enjoyed our stay in the king suite, plenty of space for parents and two kids. 1st floor close to pool, although it rained all day. The staff was helpful when we needed extra pillows and comforters. The king bed was super comfortable. The pull out sofa mattress was a little on the thin side and you ..."

Reviewed on May 26, 2026

See all 4,466 properties in Southold

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.

Surrounded by nature, come stay in this 2 bedroom private, serene location

Southold NY

Stay at this vacation home in Southold. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Croteaux Vineyards and Mattebella ...

10/10 Exceptional! (3 reviews)

"This home away from home provided a clean and comfortable space to rest and recharge, as we explored the area. Tranquil outdoor space, easy parking, yummy snacks, cozy bedding, and fine toiletries all contributed to a wonderful fall short-stay. We hope to return!M & MWestbrook, CT. USA"

Reviewed on Oct 24, 2025

Greenport Walk to beach & vineyard from this brand new home

Southold NY

Stay at this vacation home in Southold. Enjoy free WiFi, laundry facilities, and patios. Popular attractions The Old Field Vineyards and Horton Point Park are ...

10/10 Exceptional! (6 reviews)

"Amazing house, host is so friendly, right in the heart of everything! Awesome!"

Reviewed on Oct 22, 2025

Fabulous Waterfront Property in the Heart of Wine Country

Peconic NY

Stay at this cottage in Southold. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Goldsmith's Inlet Park and Sannino's Bella Vita Vineyard ...

10/10 Exceptional! (185 reviews)

"The cottage was lively with a beautiful view of the water. The house was clean and comfortable on a quiet street. There is a nice deck and yard out back. It’s located in an area with many restaurants and vineyards. I would absolutely recommend this cottage to others"

Reviewed on May 15, 2026

See all properties in Southold

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.

Popular places to visit

Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

The Old Field Vineyards

You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area.

Horton Lane Beach

Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.

Osprey's Dominion

You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Horton Point Park

Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.