Monticello Holiday Rentals

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Our top choices for Monticello holiday rentals

10.0 out of 10, Exceptional, (6)
"Great little cottage close to Bethel Woods."
United States
Erin
The price is HK$1,082
HK$2,161 total
includes taxes & fees
23 Dec - 24 Dec
Cozy Cottage with Woodstock Scavenger Hunt
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 HK$864
HK$1,831 total
includes taxes & fees
11 Jan - 12 Jan 2026
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
10.0 out of 10, Exceptional, (1)
"Taino wood was a great place for camping. Chantel and her husband Jesse are great host and are very welcoming and kind. Nice place to enjoy with your family in the nature. There were many tent sites inside their woods and we occupied the site called:Turey. We set up 3 tents (two 4-people tents and one 6-people tent). There was a firepit we used to cook food and Chantel and Jesse lend us a pot to cook. Before leaving Chantel, Jesse and a few of their friends sang indigenous songs and played...
United States
Lissette
The price is HK$444
HK$669 total
includes taxes & fees
22 Dec - 23 Dec
Arcabuco - upper camp Taino Woods, 15 minutes to Bethel Woods Concerts, Casino,
10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay. A nice quiet location. We had breakfast, lunch, and drinks and dinner on the little front patio. We will be coming back!! "
United States
June D.
The price is HK$778
HK$2,213 total
includes taxes & fees
4 Jan - 5 Jan 2026
NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail
Charming house with brook in the picturesque Village of Wurtsboro min from shops

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 HK$945
HK$1,676 total
includes taxes & fees
22 Dec - 23 Dec
Trails Head Cabin

Holiday Home in Swan Lake

In the cloud ~your cozy lake house
9.6 out of 10, Exceptional, (103)
"I loved this place. So beautiful and well furnished. "
United States
Kayla S.
The price is HK$1,387
HK$2,688 total
includes taxes & fees
22 Dec - 23 Dec
In the cloud ~your cozy lake house

Holiday Home in Liberty

Cozy two bedroom House
10.0 out of 10, Exceptional, (3)
"Very cozy stay with nice living space"
United States
Michael G.
The price is HK$1,366
HK$2,243 total
includes taxes & fees
23 Dec - 24 Dec
Cozy two bedroom House
10.0 out of 10, Exceptional, (1)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is HK$1,089
HK$1,663 total
includes taxes & fees
22 Dec - 23 Dec
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Holiday Home in Jeffersonville

Charming Creekside Village Cottage!
9.0 out of 10, Wonderful, (4)
"The cottage was exactly what we needed. Perfect size and very comfy"
United States
Lauren L.
The price is HK$817
HK$3,383 total
includes taxes & fees
14 Jan - 15 Jan 2026
Charming Creekside Village Cottage!

Holiday Home in Rock Hill

Beaver Lake Escape
9.6 out of 10, Exceptional, (29)
"Clean place, friendly and accommodating host! "
United States
Bryan A.
The price is HK$980
HK$1,716 total
includes taxes & fees
22 Dec - 23 Dec
Beaver Lake Escape
9.8 out of 10, Exceptional, (7)
"This house was perfect for our group of 6 adults. We went to two nights of concerts at Bethel Woods and this house was just down the road. It had everything we needed. "
United States
Pam M.
The price is HK$1,829
HK$4,034 total
includes taxes & fees
22 Dec - 23 Dec
Beautiful White Lake Lakehouse on Woodstock Way!

Holiday Home in Monticello

GRANDMA'S COTTAGE
9.4 out of 10, Exceptional, (18)
"The property was as presented by Vrbo and the property manager. The stay was homie, clean and comfortable."
United States
Jennifer B.
The price is HK$1,261
HK$2,292 total
includes taxes & fees
22 Dec - 23 Dec
GRANDMA'S COTTAGE

Holiday Home in Mongaup Valley

5 minutes from original Woodstock site.
9.8 out of 10, Exceptional, (61)
"Very cozy, clean and convenient "
United States
Kim K.
The price is HK$1,735
HK$2,982 total
includes taxes & fees
31 Dec - 1 Jan 2026
5 minutes from original Woodstock site.

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 HK$553
HK$969 total
includes taxes & fees
22 Dec - 23 Dec
Trails Head Tiny House

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 HK$1,401
HK$3,424 total
includes taxes & fees
31 Dec - 1 Jan 2026
Hello Small Stone
10.0 out of 10, Exceptional, (2)
"Clean, neat, well stocked cabin in a peaceful village. We enjoyed a walk on the nearby rail trail and is not far from other interesting sites. We would definitely recommend."
United States
Holly L.
The price is HK$856
HK$1,797 total
includes taxes & fees
12 Jan - 13 Jan 2026
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
10.0 out of 10, Exceptional, (9)
"Perfect little spot for our weekend visiting Stagedoor! "
United States
Kami E. Q.
The price is HK$1,167
HK$3,123 total
includes taxes & fees
12 Jan - 13 Jan 2026
Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway
The price is HK$2,327
HK$3,778 total
includes taxes & fees
31 Dec - 1 Jan 2026
Nature Escape - studio in the forest
The price is HK$934
HK$2,880 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello
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 Monticello Hotel Reviews

Find out more about Monticello

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

  • View our selection of featured holiday rentals in Monticello
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Look no further and take a look at our great range of rental properties in Monticello!

Frequently asked questions

Can I find a holiday rental in Monticello?

Yes, there are holiday rentals close to the most popular sights in Monticello, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts say Monticello is known for its live music and theatre scene. Make sure you allow time to enjoy the forests during your holiday.

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

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This highly rated holiday home rental in Monticello 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. Some other top choices in Monticello are Highland Group/Family Estate! Huge Hotub, 5 Private Units, Gameroom; 40+ guests and 5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!.

How many holiday rentals are there in Monticello?

Expedia has 31 holiday rentals for your stay in Monticello.

What can I see and do in Monticello?

Neversink River and Mongaup River are a couple of lovely local spots to get outside and enjoy nature. Monticello Casino and Raceway and Resorts World Catskills are other places to visit while you're in town.

What are holiday rentals like in Monticello?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Monticello. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.