Pine Island Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 4 - Dec 5
Tomorrow
Dec 5 - Dec 6
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Pine Island

Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Vacation Home in Warwick

9.2 out of 10, Wonderful, (7)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
The price is ￥12,841
￥22,949 total
includes taxes & fees
Dec 10 - Dec 11
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Property grounds
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Condo in Vernon Township

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 ￥13,957
￥36,608 total
includes taxes & fees
Dec 10 - Dec 11
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Dining tables
Cozy 2BR condo w/ valley views

Condo in Vernon Township

9.6 out of 10, Exceptional, (18)
"It was a wonderful stay. "
United States
Veena
The price is ￥15,281
￥39,265 total
includes taxes & fees
Dec 7 - Dec 8
Cozy 2BR condo w/ valley views
Private kitchen
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Apartment in Port Jervis

10.0 out of 10, Exceptional, (5)
"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"
United States
Jen C.
The price is ￥15,141
￥48,984 total
includes taxes & fees
Dec 7 - Dec 8
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Fridge, microwave, oven, stovetop
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Apartment in Warwick

10.0 out of 10, Exceptional, (40)
"This was the best place to stay. Host was so nice to us. If we are in the area again we would definitely stay here again. "
United States
Eileen H.
The price is ￥17,059
￥38,595 total
includes taxes & fees
Dec 17 - Dec 18
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Children's area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Cottage in Goshen

9.8 out of 10, Exceptional, (11)
"Overall Great"
United States
Nick H.
The price is ￥23,029
￥45,061 total
includes taxes & fees
Dec 16 - Dec 17
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres

Vacation Home in Goshen

2.0 star property
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
The price is ￥44,663
￥67,925 total
includes taxes & fees
Dec 14 - Dec 15
Stylish & Peaceful Getaway on 3 Private Acres
1 bedroom, desk, iron/ironing board, free WiFi
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Apartment in Montgomery

10.0 out of 10, Exceptional, (2)
"Spacey, clean, best location"
United States
Assaf B.
The price is ￥23,029
￥41,502 total
includes taxes & fees
Dec 7 - Dec 8
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Exterior
Ski-In/Ski-Out, Heated Outdoor Pool, Hot tub, Sauna, Waterpark & Biking fun!

Condo in Vernon Township

10.0 out of 10, Exceptional, (45)
"i love the hotel i will use it whenever i go to vernon "
United States
Michael P.
The price is ￥28,380
￥49,232 total
includes taxes & fees
Dec 14 - Dec 15
Ski-In/Ski-Out, Heated Outdoor Pool, Hot tub, Sauna, Waterpark & Biking fun!
Property grounds
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Cottage in Sparrow Bush

9.4 out of 10, Exceptional, (11)
"This is the most beautiful place... this is our second time staying here and we will come again. If you want peace, nature and simplicity this is worth it. The cottage is well maintained and has just about everything you need. Enjoyed or dtay here very much."
United States
Blanche R.
The price is ￥15,527
￥45,985 total
includes taxes & fees
Dec 14 - Dec 15
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Outdoor spa tub
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Vacation Home in Greenwood Lake

10.0 out of 10, Exceptional, (29)
"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 ￥23,727
￥69,648 total
includes taxes & fees
Dec 10 - Dec 11
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Property grounds
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308

Condo in Vernon Township

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay at the Appalachian Resort hosted by Milagros & Sergio. They were incredibly friendly and gave us clear and helpful explanations from the start. The room was very clean, and it was great having the water park within walking distance. They also offered flexible early check-in depending on the situation, which we really appreciated. Whenever we had questions, they responded very quickly, so we felt completely comfortable during our stay. We would love to come back again!"
United States
Young
The price is ￥19,385
￥41,516 total
includes taxes & fees
Dec 15 - Dec 16
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Vacation Home in Goshen

10.0 out of 10, Exceptional, (58)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
The price is ￥38,553
￥73,622 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Exterior
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.

Apartment in Wurtsboro

9.0 out of 10, Wonderful, (2)
"The host was very welcoming and very responsive. The apartment was very cute and super clean. I came up for a Halloween event put on by a friend the location was very convenient in the downtown area and I could walk to most of the places I needed to get to I very much enjoyed my stay here and would stay again if I’m in the area. "
United States
Sheena C.
The price is ￥20,160
￥42,366 total
includes taxes & fees
Dec 14 - Dec 15
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Aparthotel in Greenwood Lake

10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is ￥24,348
￥43,683 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Villa Verde B&B, bsm, Greenwood Lake NY
Fridge, microwave, oven, stovetop
★Scenic Views & River Access, Cozy River Home ★

Vacation Home in Montague

9.0 out of 10, Wonderful, (11)
"Had a great time. Great location close to good food and sight seeing. We will definitely book again when good weather hits. "
United States
William H.
The price is ￥13,802
￥30,098 total
includes taxes & fees
Dec 16 - Dec 17
★Scenic Views & River Access, Cozy River Home ★
Outdoor spa tub
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,

Vacation Home in Matamoras

2.0 star property
9.2 out of 10, Wonderful, (5)
"An immaculately clean, comfortable and quiet house with spacious rooms and comfortable furnishings. The owners were super friendly and responsive to our needs. We hope to stay here again next year."
United States
Denise
The price is ￥26,519
￥42,618 total
includes taxes & fees
Dec 16 - Dec 17
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
Fridge, microwave, oven, stovetop
Luxury Mountain Retreat.Minutes from ski slopes,Water Park,Resort & scenic hikes

Condo in Vernon Township

9.8 out of 10, Exceptional, (6)
"Great Place"
United States
Lenny
The price is ￥23,417
￥44,440 total
includes taxes & fees
Dec 15 - Dec 16
Luxury Mountain Retreat.Minutes from ski slopes,Water Park,Resort & scenic hikes
Fridge, microwave, stovetop, coffee/tea maker
Charming Milford-Montague Riverway Cottage

Vacation Home in Montague

8.0 out of 10, Very Good, (1)
"This location was great for our purpose of visiting family in Port Jervis and was easy to find - even in the dark. Due to the lack of reviews, I'm guessing that this is a new listing and that there are kinks still being worked out. Without going into too much detail, there was no way the space had recently been cleaned and the description provided on the listing seems to be lifted from one of their other properties as there was no fire pit, no fireplace, no dishwasher and the house is definitely...
United States
Alicia T.
The price is ￥19,160
￥37,137 total
includes taxes & fees
Dec 8 - Dec 9
Charming Milford-Montague Riverway Cottage
Sauna
Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #263

Condo in Vernon

9.8 out of 10, Exceptional, (9)
"Great owner, great place to stay, will definitely go back!"
United States
Bruce M.
The price is ￥25,239
￥48,738 total
includes taxes & fees
Dec 5 - Dec 6
Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #263
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pine Island Hotel Reviews

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Nice place great staff"
Irvin 1-night trip
Posted 12 hours ago
Hampton Inn Harriman Woodbury

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!

Frequently asked questions

Can I find a vacation rental in Pine Island?

Yes, we offer vacation rentals close to well known sights in Pine Island, or you can select a more secluded option if you're looking for relaxation. 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 vacation home rentals in Pine Island?

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries: This vacation home rental near Pine Island offers a fireplace, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 larger area.

What are vacation rentals like in Pine Island?

Vacation rentals are private properties you can book for a couple days or more in Pine Island. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip or a small group gathering.