Pine Island Holiday Rentals

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Check prices for these dates

Tonight
12 Dec - 13 Dec
Tomorrow
13 Dec - 14 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Pine Island holiday rentals

Interior
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

Holiday Home in Vernon

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries
2.0 star property
10.0 out of 10, Exceptional, (6)
"Cozy property with privacy and comfort. "
United States
Anonymous traveller
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries
Terrace/patio
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Cabin in Sussex

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
10.0 out of 10, Exceptional, (35)
"Wonderful place and cozy will book again "
United States
Alex P.
The price is HK$1,556
HK$3,209 total
includes taxes & fees
12 Jan - 13 Jan 2026
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Fireplace, books, music library, stereo
Lazy River Cottage on the Delaware River

Cottage in Matamoras

Lazy River Cottage on the Delaware River
10.0 out of 10, Exceptional, (165)
"Amazing stay "
United States
M S.
Lazy River Cottage on the Delaware River
Property grounds
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Condo in Vernon Township

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
2.5 star property
9.4 out of 10, Exceptional, (6)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
United States
Jonathan O.
The price is HK$778
HK$1,918 total
includes taxes & fees
17 Dec - 18 Dec
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Holiday Home in Vernon Township

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.4 out of 10, Exceptional, (44)
"Beautiful area"
United States
Joseph D.
The price is HK$1,113
HK$2,364 total
includes taxes & fees
20 Dec - 21 Dec
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Exterior
Modern penthouse suite in a restored grain tower with private roof deck.

Apartment in Warwick

Modern penthouse suite in a restored grain tower with private roof deck.
10.0 out of 10, Exceptional, (27)
"Wonderful stay!"
United States
Lisi M.
The price is HK$2,626
HK$4,114 total
includes taxes & fees
14 Dec - 15 Dec
Modern penthouse suite in a restored grain tower with private roof deck.
Terrace/patio
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Holiday Home in Greenwood Lake

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.
9.8 out of 10, Exceptional, (8)
"Awesome place. Cozy and great communication with owners. "
United States
Dominick P.
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.
Property grounds
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Condo in Vernon

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
10.0 out of 10, Exceptional, (70)
"We had a great stay."
United States
Laura
The price is HK$1,113
HK$2,260 total
includes taxes & fees
15 Dec - 16 Dec
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Fridge, microwave, stovetop, dishwasher
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Condo in Vernon

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
8.6 out of 10, Excellent, (92)
"Nice unit. I stay here once a year for a golf event."
United States
Kevin M.
The price is HK$1,225
HK$3,284 total
includes taxes & fees
17 Dec - 18 Dec
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
TV, fireplace
Cozy Haven: A Romantic Retreat in our Tiny House!

Cottage in Middletown

Cozy Haven: A Romantic Retreat in our Tiny House!
6.8 out of 10, (11)
"we enjoyed the cozy home it is a nice place to get away"
United States
Yidel
Cozy Haven: A Romantic Retreat in our Tiny House!
Terrace/patio
Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cabin in Wurtsboro

Cozy Loft Cabin high above Bashakill Wildlife Refuge
9.4 out of 10, Exceptional, (27)
"Loved our stay! It was only for a night but place was lovely. Lots of nature surrounding us, amazing coffee and great recommendations from host. My favorite was the winery close by, I would 1000 times come back for this. Thank you for your hospitality "
United States
Kimberly G.
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres

Holiday Home in Goshen

Stylish & Peaceful Getaway on 3 Private Acres
2.0 star property
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
The price is HK$2,241
HK$3,384 total
includes taxes & fees
13 Dec - 14 Dec
Stylish & Peaceful Getaway on 3 Private Acres
Fridge, microwave, oven, stovetop
Mountain Creek/Great Gorge Village 2 Bedroom Condo W/Loft

Condo in Vernon

Mountain Creek/Great Gorge Village 2 Bedroom Condo W/Loft
8.4 out of 10, Very good, (24)
"It was a very short distance to Mtn Creek for the race weekend "
United States
Daniel G.
The price is HK$1,556
HK$2,874 total
includes taxes & fees
24 Dec - 25 Dec
Mountain Creek/Great Gorge Village 2 Bedroom Condo W/Loft
Dining
Serene Rustic Retreat with Lake

Cabin in Cuddebackville

Serene Rustic Retreat with Lake
2.0 star property
10.0 out of 10, Exceptional, (8)
"Amazing stay and beautiful home!"
United States
Koby A.
The price is HK$1,556
HK$3,716 total
includes taxes & fees
14 Dec - 15 Dec
Serene Rustic Retreat with Lake
Interior
Luxury 9BR Retreat w/Pool & Hot Tub

Villa in Chester

Luxury 9BR Retreat w/Pool & Hot Tub
7.0 out of 10, Good, (2)
"Pool was not open or usable but we were not interested in doing that "
United States
John D.
Luxury 9BR Retreat w/Pool & Hot Tub
Outdoor spa tub
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Holiday Home in Greenwood Lake

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
10.0 out of 10, Exceptional, (30)
"We loved the house. It was a perfect and much needed short getaway for my husband and I. We brought our little dog Lenny and he loved it too! "
United States
Chelsea D.
The price is HK$1,296
HK$3,579 total
includes taxes & fees
17 Dec - 18 Dec
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Indoor pool, outdoor pool
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking

Chalet in vernon

Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
9.4 out of 10, Exceptional, (56)
"The house was so comfortable and had everything we needed to catch up over our girl's weekend. The porches and the living room were both excellent gathering spaces and we loved being so close to the spa. You can't beat the location and the house was lovely! The owners were also really responsive to questions we had over our stay. "
United States
Cailyn M.
The price is HK$1,655
HK$3,784 total
includes taxes & fees
14 Dec - 15 Dec
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
Interior
Hike & Fish: Outdoor Retreat Near Trails

Cottage in Westbrookville

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
The price is HK$1,284
HK$2,394 total
includes taxes & fees
12 Jan - 13 Jan 2026
Hike & Fish: Outdoor Retreat Near Trails
Outdoor pool, a heated pool
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Holiday Home in Vernon

Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
9.8 out of 10, Exceptional, (88)
"We loved our stay! This house was perfect for our family (6 adults) 3 teenagers. Everyone had their own space, the backyard was our favorite place to hang. Close to waterpark. Tennis court was a big bonus! We can’t wait to come back during the winter for a snowboard trip! "
United States
Meagan B.
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is HK$1,221
HK$2,218 total
includes taxes & fees
12 Jan - 13 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY
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.
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Top Pine Island Hotel Reviews

Tru by Hilton Middletown

Tru by Hilton Middletown

10/10 Excellent
"Staff both during check in and out were great . Great stay ."
david 1-night trip
Posted 2 days ago
Tru by Hilton Middletown

Find out more about Pine Island

Search for holiday rentals in Pine Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Pine Island using one of the methods below:

  • View our selection of featured holiday rentals in Pine Island
  • Use the map to find apartments and other holiday homes in the Pine Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pine Island while they last

Look no further and take a look at our great range of rental properties in Pine Island!

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Frequently asked questions

Can I find a holiday rental in Pine Island?

Yes, there are holiday rentals close to the most popular sights in Pine Island, or you can select a more secluded option if you're looking for a relaxing stay. Pine Island is known for its golf courses and mountain views. Make sure you have time to check out the riverfront while you're in the area.

What are some of the best holiday rentals that Pine Island has to offer?

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries: This holiday home rental outside of Pine Island offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Pine Island?

While exploring the area, visit family-friendly sights like Mountain Creek Waterpark, or get outside and enjoy nature at Pine Island Town Park. Scenic Farms Golf Course and Warwick Valley Winery and Distillery are a couple of places you'll find in the wider area.

What are holiday rentals like in Pine Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pine Island. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip.