Cuddebackville Holiday Rentals

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Our top choices for Cuddebackville holiday rentals

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 AU$724
includes taxes & fees
3 Jan - 4 Jan 2026
Serene Rustic Retreat with Lake
The price is AU$1,196
includes taxes & fees
30 Dec - 31 Dec
Riverfront Retreat | Hot Tub, Firepit & Pool Table
The price is AU$187
includes taxes & fees
30 Dec - 31 Dec
Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is AU$232
includes taxes & fees
5 Jan - 6 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Holiday Home in Rock Hill

Trails Head Tiny House
9.0 out of 10, Wonderful, (19)
"Host was very friendly and helpful. "
United States
Michael R.
The price is AU$188
includes taxes & fees
30 Dec - 31 Dec
Trails Head Tiny House

Cabin in Rock Hill

Trails Head Cabin
9.8 out of 10, Exceptional, (98)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
The price is AU$327
includes taxes & fees
4 Jan - 5 Jan 2026
Trails Head Cabin
10.0 out of 10, Exceptional, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is AU$390
includes taxes & fees
11 Jan - 12 Jan 2026
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
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 AU$406
includes taxes & fees
21 Jan - 22 Jan 2026
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
10.0 out of 10, Exceptional, (46)
"i love the hotel i will use it whenever i go to vernon "
United States
Michael P.
The price is AU$437
includes taxes & fees
6 Jan - 7 Jan 2026
Lifts OPEN! Rustic Chic at Mountain Creek! Heated Outdoor Pool, Hot Tubs, Sauna
10.0 out of 10, Exceptional, (7)
"The house was adorable! It had all amenities. The hosts were super responsive. Definitely would stay there again. "
United States
Chris L.
The price is AU$354
includes taxes & fees
5 Jan - 6 Jan 2026
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
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 AU$411
includes taxes & fees
8 Jan - 9 Jan 2026
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
2.0 star property
The price is AU$1,287
includes taxes & fees
5 Jan - 6 Jan 2026
2 Lake Cabins Pool+hottub Game Room 23acs
10.0 out of 10, Exceptional, (6)
"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 AU$482
includes taxes & fees
12 Jan - 13 Jan 2026
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
9.4 out of 10, Exceptional, (11)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
United States
Nicholas G.
The price is AU$429
includes taxes & fees
12 Jan - 13 Jan 2026
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Chalet in Narrowsburg

The Chalet - Rustic Retreat
9.0 out of 10, Wonderful, (11)
"Fantastic stay. Quiet area, close to Narrowsburg, friendly neighbors. Super clean, fire pit area is very nice and we love the hot tub after a day on the river!"
United States
Jeff H.
The price is AU$535
includes taxes & fees
5 Jan - 6 Jan 2026
The Chalet - Rustic Retreat
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is AU$440
includes taxes & fees
3 Jan - 4 Jan 2026
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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 AU$377
includes taxes & fees
27 Jan - 28 Jan 2026
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Cottage in Middletown

Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is AU$624
includes taxes & fees
31 Dec - 1 Jan 2026
Hello Small Stone

Condo in Vernon Township

Cozy 2BR condo w/ valley views
9.6 out of 10, Exceptional, (18)
"It was a wonderful stay. "
United States
Veena
The price is AU$417
includes taxes & fees
20 Jan - 21 Jan 2026
Cozy 2BR condo w/ valley views
9.8 out of 10, Exceptional, (6)
"Great Place"
United States
Lenny
The price is AU$469
includes taxes & fees
28 Jan - 29 Jan 2026
Luxury Mountain Retreat.Minutes from ski slopes,Water Park,Resort & scenic hikes
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 Cuddebackville Hotel Reviews

Find out more about Cuddebackville

Everything you need to know about Cuddebackville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cuddebackville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cuddebackville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cuddebackville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cuddebackville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cuddebackville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuddebackville holiday rentals we have selected for you start as low as AU$327 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cuddebackville rentals

At Expedia, we put the best Cuddebackville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cuddebackville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cuddebackville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cuddebackville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Cuddebackville?

Yes, there are holiday rentals in Cuddebackville close to Oakland Valley Race Park, or you can select a more secluded option if you're looking for a relaxing stay.

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

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This holiday home rental outside of Cuddebackville is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Cuddebackville?

Choose from 4 Expedia holiday rentals in Cuddebackville for a memorable holiday.

What can I see and do in Cuddebackville?

Enjoy the outdoors at Neversink River and Delaware and Hudson Canal County Park, or simply take in cultural attractions like Neversink Valley Area Museum and Neversink Valley Museum of History & Innovation. In the wider area, you’ll find Oakland Valley Race Park and The Hawk's Nest Lookout.

What are holiday rentals like in Cuddebackville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cuddebackville. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family gatherings.