Cheap Vacations in Shelter Island

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3-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $418, price is now $270 per person
$270
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
Price was $617, price is now $381 per person
$381
per person
Jan 28 - Jan 31
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (NYC)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $1,245, price is now $780 per person
$780
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
Price was $627, price is now $405 per person
$405
per person
Jan 28 - Jan 31
found 19 hours ago
Roundtrip flight included
Dallas (DAL) to New York (NYC)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,057, price is now $687 per person
$687
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,499, price is now $982 per person
$982
per person
Jan 8 - Jan 11
found 19 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New York (NYC)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Price was $1,506, price is now $1,001 per person
$1,001
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (NYC)
Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Save 100% on your flight
Price was $1,679, price is now $1,120 per person
$1,120
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
Roxy Hotel New York

Roxy Hotel New York

4.5 out of 5
Save 100% on your flight
Price was $806, price is now $538 per person
$538
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $517, price is now $353 per person
$353
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Save 100% on your flight
Price was $625, price is now $428 per person
$428
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
The Iroquois New York

The Iroquois New York

4.5 out of 5
Save 100% on your flight
Price was $608, price is now $416 per person
$416
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)

4-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

3 out of 5
Price was $380, price is now $280 per person
$280
per person
Jan 10 - Jan 14
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to Islip (ISP)
Oheka Castle Hotel & Estate

Oheka Castle Hotel & Estate

3.5 out of 5
Save 100% on your flight
Price was $1,363, price is now $729 per person
$729
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $1,353, price is now $829 per person
$829
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,469, price is now $1,015 per person
$1,015
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (NYC)
Le Meridien New York, Central Park by Marriott

Le Meridien New York, Central Park by Marriott

4 out of 5
Save 100% on your flight
Price was $849, price is now $588 per person
$588
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Ace Hotel New York

Ace Hotel New York

4 out of 5
Save 100% on your flight
Price was $683, price is now $479 per person
$479
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
The Frederick Hotel

The Frederick Hotel

4 out of 5
Save 100% on your flight
Price was $538, price is now $385 per person
$385
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Save 100% on your flight
Price was $447, price is now $327 per person
$327
per person
Jan 10 - Jan 14
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
The Renwick

The Renwick

4 out of 5
Save 100% on your flight
Price was $835, price is now $612 per person
$612
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (NYC)
Hyatt House Jersey City

Hyatt House Jersey City

3.5 out of 5
Save 100% on your flight
Price was $571, price is now $421 per person
$421
per person
Jan 7 - Jan 11
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $643, price is now $474 per person
$474
per person
Jan 7 - Jan 11
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Z Hotel

Z Hotel

2 out of 5
Price was $449, price is now $333 per person
$333
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

5-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
The Gallivant Times Square

The Gallivant Times Square

3.5 out of 5
Save 100% on your flight
Price was $555, price is now $357 per person
$357
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Price was $1,169, price is now $592 per person
$592
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Price was $3,426, price is now $1,940 per person
$1,940
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,043, price is now $621 per person
$621
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Save 100% on your flight
Price was $787, price is now $474 per person
$474
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $750, price is now $462 per person
$462
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $654, price is now $408 per person
$408
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,629, price is now $1,054 per person
$1,054
per person
Jan 28 - Feb 2
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Outsite Chelsea

Outsite Chelsea

2 out of 5
Save 100% on your flight
Price was $675, price is now $450 per person
$450
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
The Iroquois New York

The Iroquois New York

4.5 out of 5
Save 100% on your flight
Price was $966, price is now $646 per person
$646
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Le Meridien New York, Central Park by Marriott

Le Meridien New York, Central Park by Marriott

4 out of 5
Save 100% on your flight
Price was $1,018, price is now $681 per person
$681
per person
Jan 28 - Feb 2
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Hotel Belleclaire

Hotel Belleclaire

4 out of 5
Save 100% on your flight
Price was $733, price is now $499 per person
$499
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)

6-7 night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $685, price is now $406 per person
$406
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Price was $1,342, price is now $667 per person
$667
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Price was $4,081, price is now $2,311 per person
$2,311
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,207, price is now $710 per person
$710
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Save 100% on your flight
Price was $889, price is now $526 per person
$526
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $2,643, price is now $1,566 per person
$1,566
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $866, price is now $524 per person
$524
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Hotel 57

Hotel 57

4 out of 5
Save 100% on your flight
Price was $737, price is now $457 per person
$457
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Hyatt House Jersey City

Hyatt House Jersey City

3.5 out of 5
Save 100% on your flight
Price was $799, price is now $495 per person
$495
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
Save 100% on your flight
Price was $823, price is now $514 per person
$514
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,921, price is now $1,231 per person
$1,231
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
Gansevoort Meatpacking

Gansevoort Meatpacking

5 out of 5
Save 100% on your flight
Price was $2,024, price is now $1,306 per person
$1,306
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)

Flight deals to Shelter Island

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jan 29 - Sun, Feb 1
MIA
Miami
LGA
New York
$59 Roundtrip, found 2 hours ago
$59
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Jan 29 from Miami to New York, returning Sun, Feb 1, priced at $59 found 2 hours ago
Thu, Jan 22 - Mon, Jan 26
MCO
Orlando
JFK
New York
$59 Roundtrip, found 6 days ago
$59
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Orlando to New York, returning Mon, Jan 26, priced at $59 found 6 days ago
Wed, Jan 21 - Tue, Jan 27
MCO
Orlando
EWR
New York
$62 Roundtrip, found 3 days ago
$62
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Orlando to New York, returning Tue, Jan 27, priced at $62 found 3 days ago

Top rated hotels for your Shelter Island vacation

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
18.43 mi from city center
$472 nightly
The price is $539 total per night
$539 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Located in Montauk, Gurney's Montauk Resort & Seawater Spa is by the ocean, a 3-minute drive from Hither Hills State Park and 7 minutes from Shadmoor State Park.
On private beach
Pool
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
15.48 mi from city center
$79 nightly
The price is $91 total per night
$91 total
Dec 7 - Dec 8
Total with taxes and fees
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Saybrook Country Barn.
Pet friendly
Parking included
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
3.59 mi from city center
$237 nightly
The price is $271 total per night
$271 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
On private beach
Pool
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.