Sherwood Island State Park Adventure Vacations

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Top Adventure vacation packages in Sherwood Island State Park

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
Price was $578, price is now $469 per person
$469
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.2/10 Very Good! (1,017 reviews)
Fabulous location next to great restaurants and shopping. Dramatic lobby, fabulous common spaces and fabulous bar. Half way between Greenwich and Stamford Ct. An architectural gem Close to Long Island Sound

Reviewed on Oct 24, 2025

Delamar Southport

Delamar Southport

4 out of 5
Save 100% on your flight
Price was $1,122, price is now $837 per person
$837
per person
Jan 2 - Jan 7
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
9.4/10 Exceptional! (434 reviews)
It's in the heart of the city and easy walking distance to many of the historic sites

Reviewed on Oct 5, 2025

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Save 100% on your flight
Price was $1,538, price is now $1,202 per person
$1,202
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
9.4/10 Exceptional! (943 reviews)
Front desk staff went above and beyond—helpful, accommodating, and genuinely kind. They assisted with multiple requests, even ones unrelated to the hotel, including calling off-site dry cleaning services to arrange pickup for us. The rooms were beautiful and well maintained, and the location is picturesque—just a short, pleasant walk to town with plenty of dining and sightseeing options. Would definitely stay here again.

Reviewed on Oct 21, 2025

Luxury Apartments by Hyatus at The Asher

Luxury Apartments by Hyatus at The Asher

4.5 out of 5
Downtown Stamford
Save 100% on your flight
Price was $958, price is now $755 per person
$755
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
10/10 Exceptional! (18 reviews)
This place truly felt like a home away from home. Everything was spotless, comfortable, and well cared for. The location made it easy to access everything we needed, whether dining, shopping, or exploring the area. I would definitely return!

Reviewed on Sep 22, 2025

Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Price was $837, price is now $675 per person
$675
per person
Dec 19 - Dec 24
found 17 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
5.8/10 (64 reviews)
My husband has cancer, and we had to cancel our vacation to accommodate his tests. We live an hour+ away from Stamford, so we thought we'd spend the night there so we wouldn't have to get up early to drive to the testing site. And try to make a fun stay in the middle of this difficult time. So I was disappointed that it wasn't in better shape. Plusses: the room was clean and spacious, the wifi and elevator worked. The sofa was hard but comfy enough, and we watched a couple of TV shows. We didn't use the kitchen, but the counters were damaged. Cosmetic, but it added to a negative overall impression. Minuses: The room smelled of the cleaner hotels use to mask the smell of smoke. The whole place did. The bathroom light was very dim. The shower had a handheld shower head and no door, so the water went everywhere. I cleaned it up. The water temperature was impossible to control and I nearly scalded myself. The toilet made scary noises after flushing, but nothing bad happened. The bedroom lights: 2 out of 5 worked: 1 worked after we jiggled the base and tightened the bulb, the two reading lights didn't work at all. One of them lacked a bulb. The bed was very uncomfortable. Mattress too hard, pillows too soft. I'm a mess of aches today. Breakfast was continental, serve yourself. Your choice of carb, plus coffee, tea, and milk.

Reviewed on Sep 25, 2025

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5* Adventure vacations in Sherwood Island State Park

Price found within the past 48 hours. Click for updated prices.
The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection

5 out of 5
Price was $1,268, price is now $1,169 per person
$1,169
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
9.2/10 Wonderful! (515 reviews)
Beautiful hotel. Great location.

Reviewed on Sep 7, 2025

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3 Night Adventure vacations in Sherwood Island State Park

Price found within the past 48 hours. Click for updated prices.
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
Price was $300, price is now $250 per person
$250
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.6/10 Excellent! (1,008 reviews)
Clean, quiet, not many people. Great customer service

Reviewed on Oct 23, 2025

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
Price was $503, price is now $421 per person
$421
per person
Dec 26 - Dec 29
found 15 hours ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
8.2/10 Very Good! (1,017 reviews)
Fabulous location next to great restaurants and shopping. Dramatic lobby, fabulous common spaces and fabulous bar. Half way between Greenwich and Stamford Ct. An architectural gem Close to Long Island Sound

Reviewed on Oct 24, 2025

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
Price was $503, price is now $433 per person
$433
per person
Dec 25 - Dec 28
just found
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
8.8/10 Excellent! (1,363 reviews)
Property/furnishings could use updating. TV's are small and old.

Reviewed on Oct 22, 2025

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4 Night Adventure vacations in Sherwood Island State Park

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains

2 out of 5
Save 100% on your flight
Price was $374, price is now $279 per person
$279
per person
Nov 28 - Dec 2
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
6.8/10 (1,024 reviews)
The property was okay the room was nice and clean

Reviewed on Oct 23, 2025

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Save 100% on your flight
Price was $768, price is now $446 per person
$446
per person
Dec 26 - Dec 30
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,002 reviews)
Nice clean hotel in lower westchester

Reviewed on Oct 19, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $539, price is now $387 per person
$387
per person
Dec 26 - Dec 30
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,021 reviews)
Fantastic property and location. Incredible history and staff was helpful.

Reviewed on Oct 23, 2025

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Find awesome Sherwood Island State Park adventure vacations

How can I book the best Sherwood Island State Park adventure trips?

Choose your own adventure in Sherwood Island State Park, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Sherwood Island State Park family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Sherwood Island State Park. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Sherwood Island State Park adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Sherwood Island State Park adventure vacation for couples?

Book a Sherwood Island State Park couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Sherwood Island State Park?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Sherwood Island State Park with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Sherwood Island State Park adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.