Monticello Holiday Rentals

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Check prices for these dates

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Monticello

5 bedrooms, desk, iron/ironing board, free WiFi
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Monticello
9.0 out of 10, Wonderful, (87)
"This is a perfect place for a large group to stay and not get bored! Lots of space inside and out. Super clean, and well maintained. The host replied to my messages super quick! Totally recommend this property!"
United States
Anonymous traveller
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Interior
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Monticello
9.6 out of 10, Exceptional, (50)
"Amazing spot in the Catskills! Plenty of beds and rooms."
United States
Taurance R.
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Fridge, microwave, oven, stovetop
Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests

Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests

2.0 star property
Monticello
8.0 out of 10, Very good, (4)
"We had the BEST time staying here with our sorority sisters! The property is absolutely perfect for groups — so many private bedrooms that gave everyone their own space, plus the cutest houses and cabins that made it feel like a little village just for us. The dining hall was super chill and such a great hangout spot for meals and late-night laughs.We loved how close it was to everything — food, fun activities, and plenty of outdoor space to enjoy the yard. It made planning so easy since...
United States
Nancy D.
Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests
Outdoor spa tub
Modern Chalet with Hot Tub and Lake Access

Modern Chalet with Hot Tub and Lake Access

Thompson
10.0 out of 10, Exceptional, (5)
"The property is very cool and secluded. We had a nice, relaxing time!"
United States
Ben N.
Modern Chalet with Hot Tub and Lake Access
Exterior detail
GRANDMA'S COTTAGE

GRANDMA'S COTTAGE

Monticello
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$1,400
HK$2,466 total
includes taxes & fees
28 Nov - 29 Nov
GRANDMA'S COTTAGE
Outdoor spa tub
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Monticello
8.2 out of 10, Very good, (24)
"This place was very nice and clean. It was the perfect size and we had a good time here. We definitely recommend! "
United States
Alexa W.
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski
Exterior
Catskills Lakefront Escape with Hot Tub

Catskills Lakefront Escape with Hot Tub

Thompson
9.8 out of 10, Exceptional, (19)
"Place was great and the pictures were very representative of the house. Host was super communicative, easy check in and check out."
United States
Matthew O.
Catskills Lakefront Escape with Hot Tub
TV, fireplace, table football, offices
The Compound by Malon Villas

The Compound by Malon Villas

Monticello
10.0 out of 10, Exceptional, (2)
"We had a large group and this place could not have been more perfect, we had a blast. It is enormous there were 15 bedrooms total, including some bunk rooms and plenty of room for everyone. The pool is amazing and warm, the pool room is enormous. The sauna and hot tub were fantastic. We will hopefully return sooner than later, it was a great winter stay and I'm sure it's amazing in the summer too. "
United States
Elena B.
The Compound by Malon Villas
Exterior
Unique Escapes

Unique Escapes

3.0 star property
Monticello
10.0 out of 10, Exceptional, (2)
Unique Escapes
Indoor pool, outdoor pool
Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

Monticello
9.4 out of 10, Exceptional, (34)
"We have gone back to this location three times because it's an excellent value with many bedrooms for our large group. The property manager was very responsive to any needs during our stay. The kitchen might use an upgrade, but the rest of the property is very good."
United States
Joseph M.
Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!
Outdoor dining
New Custom A-Frame in Swinging Bridge Lake Community

New Custom A-Frame in Swinging Bridge Lake Community

Monticello
10.0 out of 10, Exceptional, (22)
"Great location- I loved the wildlife there and access to all the attractions that we wanted to see. "
United States
Gregory B.
New Custom A-Frame in Swinging Bridge Lake Community
10 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful 10-Bedroom Home for Group Getaways

Beautiful 10-Bedroom Home for Group Getaways

Thompsonville
8.0 out of 10, Very good, (1)
"The landscape is beautiful. There’s much to explore. It is a convenient location. The fire pit was a highlight. Toasting marshmallows and grilling. The house is tastefully decorated. The water pressure in sinks and showers is very very slow. The layout is a bit of a maze. There’s a center staircase that splits. Half of the sleepy areas on two side. The description of 10 bedrooms is deceptive. Each of the bedrooms has a lounge area. These areas are spacious and have sofas that fold out; not...
United States
Leah
Beautiful 10-Bedroom Home for Group Getaways
Terrace/patio
Modern 3-bedroom cabin with Hot Tub and Private Pond

Modern 3-bedroom cabin with Hot Tub and Private Pond

Monticello
9.8 out of 10, Exceptional, (21)
"Th"
United States
Lisa H.
Modern 3-bedroom cabin with Hot Tub and Private Pond
3 bedrooms, desk, iron/ironing board, travel cot
Lakefront Catskills Escape with Hot Tub, Game Room, and Theater!

Lakefront Catskills Escape with Hot Tub, Game Room, and Theater!

Monticello
9.6 out of 10, Exceptional, (7)
"Came with a group of girls for my sister's bachelorette. Had an amazing time and the house was beautiful! Appreciated the host's quick response to my questions."
United States
Corey R.
Lakefront Catskills Escape with Hot Tub, Game Room, and Theater!
Fridge, microwave, oven, stovetop
Sun Drenched Lakefront Cove

Sun Drenched Lakefront Cove

Thompson
9.0 out of 10, Wonderful, (28)
"This was my second time staying here and I have another stay booked already. We love it and will continue to keep coming back. "
United States
Beth N.
Sun Drenched Lakefront Cove
On the beach
Marina Hillside Lakefront Retreat

Marina Hillside Lakefront Retreat

Thompson
10.0 out of 10, Exceptional, (2)
"We had a great stay in this nice lake house. Fun beach, kayaks and a marina next door to rent even bigger boats!"
United States
Christine N.
Marina Hillside Lakefront Retreat
Outdoor dining
Modernist Lakefront Sojourn

Modernist Lakefront Sojourn

Thompson
9.0 out of 10, Wonderful, (4)
"Nice place, plenty of room, great view of the lake."
United States
Sheryl B.
Modernist Lakefront Sojourn
Fridge, microwave, oven, stovetop
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Forestburgh
9.6 out of 10, Exceptional, (4)
"Cool house in a quiet setting!"
United States
Steve M.
Serenity at Lake Joseph | Lakefront•Hot Tub•Ski
Terrace/patio
Secluded lakefront home With an EV charger

Secluded lakefront home With an EV charger

Monticello
9.8 out of 10, Exceptional, (12)
"My family and I were looking for a secluded and quiet place to unwind for vacation. This place did not disappoint, the house had everything we could possibly need!"
United States
Suzanne M.
Secluded lakefront home With an EV charger
Exterior
Whimsical Lakefront Chalet

Whimsical Lakefront Chalet

Thompson
9.6 out of 10, Exceptional, (9)
"The property was great and we had a blast. Only wish there were more blankets available as it got super chilly!"
United States
Mariel S.
Whimsical Lakefront Chalet
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

Best Western Monticello

Best Western Monticello

10/10 Excellent
"The room was wonderful and the staff so friendly! Loved the location! Great Italian restaurant next door! We plan to stay here again!"
Joan 1-night trip
Posted 17 hours ago
Best Western Monticello

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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  • Enter your travel dates to view the best deals on holiday rentals in Monticello while they last

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 5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation! and Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests.

How many holiday rentals are there in Monticello?

Expedia has 29 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.