Find 4 Star Hotels in North Main Street Historic District, NY from $231

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Check availability on North Main Street Historic District 4 Star Hotels

Our top choices for North Main Street Historic District 4-star hotels

Indoor pool, seasonal outdoor pool, sun loungers
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.2 out of 10, Very Good, (697)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
$420 nightly
The price is $480
Dec 18 - Dec 19
Total with taxes and fees
Gurney's Montauk Resort & Seawater Spa
Resort view
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$212 nightly
The price is $242
Jan 11 - Jan 12, 2026
Total with taxes and fees
Sound View Greenport
2 restaurants, breakfast served
Montauk Yacht Club

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1000)
"Great hotel. Would like to come stay again in the summer."
United States
Stefania
Montauk Yacht Club
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Canoe Place Inn and Cottages

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (60)
"Amazing property. Really enjoyed our stay."
United States
Dave
$431 nightly
The price is $492
Jan 9 - Jan 10, 2026
Total with taxes and fees
Canoe Place Inn and Cottages
View from room
Hero Beach Club

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
$232 nightly
The price is $265
Dec 28 - Dec 29
Total with taxes and fees
Hero Beach Club
Courtyard Balcony King | Courtyard view
Marram

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (252)
"It was an amazing relaxing weekend. We want to come back next year the same weekend!"
United States
Piera
Marram
View from property
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.0 out of 10, Wonderful, (160)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
$223 nightly
The price is $255
Jan 5 - Jan 6, 2026
Total with taxes and fees
Journey East Hampton
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (141)
"Great get away "
United States
Charles
$203 nightly
The price is $231
Dec 25 - Dec 26
Total with taxes and fees
Silver Sands Motel & Beach Bungalows
Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (91)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
$624 nightly
The price is $713
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Roundtree, Amagansett
2 restaurants, American cuisine
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (161)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
$263 nightly
The price is $343
Dec 14 - Dec 15
Total with taxes and fees
The 1770 House Restaurant & Inn
Outdoor pool
Topping Rose House

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (136)
"Great rooms, staff and food"
United Kingdom
Alexandra
$547 nightly
The price is $629
Dec 12 - Dec 13
Total with taxes and fees
Topping Rose House
Property entrance
The Maidstone

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
$272 nightly
The price is $311
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Maidstone
Terrace/patio
The Pridwin Hotel

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84)
"Overall the places is nice, clean and great views"
United States
Dianne
The Pridwin Hotel
Aerial view
East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
$437 nightly
The price is $499
Dec 15 - Dec 16
Total with taxes and fees
East Hampton Art House Bed & Breakfast
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
Offshore Residences

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
$579 nightly
The price is $662
Dec 14 - Dec 15
Total with taxes and fees
Offshore Residences
Exterior
The Rams Head Inn

The Rams Head Inn

The Rams Head Inn
4.0 star property
Shelter Island Heights
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
United States
Lana
$395 nightly
The price is $451
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Rams Head Inn
Private kitchen
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
$1,798 nightly
The price is $2,055
Dec 21 - Dec 22
Total with taxes and fees
Canoe Place Waterfront Residences
Exterior
Faraway Sag Harbor

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292)
"staff seemed tired and fed up of people staying!"
United Kingdom
andrew
Faraway Sag Harbor
Reception hall
434 on Main

434 on Main

434 on Main
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (36)
"Great hosts"
United States
David
434 on Main
Smart TV, fireplace, table tennis, stereo
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
4.0 star property
Sag Harbor
10.0 out of 10, Exceptional, (11)
"Great house, close to the town, would definitely rent again "
United States
Jared W.
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in North Main Street Historic District.
Mill House Inn

Mill House Inn

31 North Main Street East Hampton NY
$330 nightly
The price is $377 total per night from Dec 14 to Dec 15
$377 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (73 reviews)
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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.

Top North Main Street Historic District Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"EVERYTHING about our stay at Gurneys was wonderful. The staff was outstanding and so accommodating. The room was beautiful looking out at the ocean. We have decided to make a family tradition to go to stay."
Rachel 1-night trip
Posted 4 days ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are the best 4-star hotels in North Main Street Historic District?
The Maidstone and Journey East Hampton are two top-rated retreats located around North Main Street Historic District. Both have a 4-star rating and promise premium comfort alongside an unrivaled traveler experience. Check in to the first and get access to Frette Italian sheets and premium bedding. The second features premium bedding and a swimming pool, among many amenities.
How much does it cost to stay in a 4-star hotel in North Main Street Historic District?
Expedia can help you quickly find the ideal 4-star hotel for your vacation in North Main Street Historic District. Use our handy filter tool to tailor your search by things like price, conveniences and hotel star rating and get access to awesome deals in a few clicks.

  • Search for the lowest price from $377

What's the difference between 5-star and 4-star hotels in North Main Street Historic District?
Offering an inviting traveler experience and upmarket décor, 4-star hotels are a fantastic option for your North Main Street Historic District break. These kinds of accommodations generally feature loads of handy amenities that make it a breeze to kick back and relax — think 24-hour room service, pools and restaurants. Or live in the lap of luxury at a 5-star hotel designed to indulge you in high-end perks and amenities. A personalized service, oversized bathrooms and fine dining are typically featured at these swanky properties.