Monticello vacation rentals

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Top-rated vacation rentals in Monticello

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Monticello

4.92 out of 5 average rating, 130 reviews

Cozy Catskill Getaway Upstate NY - 5 min to casino

Kick back and relax in this cozy styled cottage! Centrally located near shopping plazas including Shoprite, Walmart and Marshalls. Also close to eateries, fast food restaurants, and Resorts World Casino. Explore the Catskills and come back to stay in a warm cottage. Although it is centrally located, it's pushed back enough that you still get the country living feeling. Located on 2 acres of land, you're sure to hear the birds chirping! There is a pull out couch available for an additional guest.

May 7 – 14

R2,513 ZAR per night

Guest favorite

Cabin in Smallwood

4.85 out of 5 average rating, 202 reviews

Comfortable Catskill Cabin minutes to Bethel Woods

Comfortable, private home very close to Bethel Woods on a quiet dead-end street in a desirable mountain lake community. Two bedrooms & a loft, WiFi, heat/AC, deck with BBQ grill, picnic table & fire pit. In the heart of the Sullivan County Catskills centrally located to the many attractions this vacation recreation area has to offer: site seeing, concerts, hiking, camping, skiing, breweries/wineries, boating, parks, antiquing, casinos, wedding venues, museums, Delaware River, hunting/fishing etc

Jun 22 – 29

R2,770 ZAR per night

Guest favorite

Cottage in Narrowsburg

4.99 out of 5 average rating, 143 reviews

Cozy Cottage in Popular Narrowsburg

A sweet cottage in the artsy hamlet of Narrowsburg welcomes you for a quiet retreat in the country. Moments from the Delaware River and the village, spend hours taking in the serenity of the river and rolling hills of the surrounding countryside, or popping into town for arts and entertainment. There are two separate bedrooms, one with a queen bed and one with a full bed; a well-equipped kitchen; WiFi; a front and back porch; and a deck Come enjoy the all-season splendor of Sullivan County

May 28 – Jun 4

R2,602 ZAR per night

Guest favorite

Cabin in Monticello

4.9 out of 5 average rating, 101 reviews

Blue House: cedar hot tub, deck, bbq, hike

Nestled in the Catskills Mountain region, between the Delaware and Hudson Rivers in the community of Monticello. Insta @bluehouseofcatskills offers a year-round retreat away from the hustle and bustle of the city. Spectacular stary nights, wildlife in the backyard, hiking trails, swimming and skiing all a short drive away. The Blue House is a wonderful getaway for all to enjoy. Modern and contemporary design the Blue House offers comfortable king and queen bedrooms and a spacious living area.

Dec 4 – 11

R3,714 ZAR per night

Guest favorite

Cabin in Wurtsboro

4.98 out of 5 average rating, 201 reviews

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

Sep 26 – Oct 3

R6,816 ZAR per night

Guest favorite

Cabin in Mongaup Valley

4.92 out of 5 average rating, 284 reviews

Cozy Post & Beam Barn Cabin w/Park near Bethel

1200 sq. ft Post & Beam 2 story Barn Cabin set on 18+ acres of property w/1250 ft. of rd frontage leading to this gem. Amish wood furniture and a wood burning stove. Open loft concept on 2nd floor offers 1 king bed, a trundle bed with 2 twins (sleeps 4), 1/2 bath & closet space. Downstairs offers kitchen, dining room, living room and full bath. Private park on property w/hammock, volleyball & basketball court, swing set, slide & playhouse, yard games (in house & shed) barbecue & firepit.

Sep 18 – 25

R2,637 ZAR per night

Guest favorite

Home in Narrowsburg

4.95 out of 5 average rating, 159 reviews

Modern Getaway in the Catskills

Our summer rental has a private entrance adjacent to the main house with kitchen, living & dining rooms, 1 bedroom w/ Queen bed , AC and 1.5 baths. A porch w/ patio furn. a charcoal BBQ and 50 wooded acres to explore. We supply sheets, towels, kitchenware, coffeemaker and 2 flat screen satellite TVs, Internet and WiFi. A great get-a-way for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets or animals or children. All are welcome. Rainbow Friendly.

Apr 11 – 18

R1,675 ZAR per night

Guest favorite

Cabin in Rock Hill

4.89 out of 5 average rating, 310 reviews

Trails Head Cabin

Welcome to Trails Head Cabin! Located on a quiet dead end road, this cabin sits at the head of the Neversink River unique area and offers activities such as hiking, fishing and hunting. My wife and I have fully renovated the inside of the cabin, and have begun to update the exterior. A five minute drive to Resorts World Casino and Holiday Mountain Ski and Fun Park. A twenty-five minute drive to Bethel Woods Center for the Arts (sight of the 1969 Woodstock Festival). See you soon!

Dec 16 – 23

R3,140 ZAR per night

Guest favorite

Cottage in Monticello

4.94 out of 5 average rating, 326 reviews

Modern Upstate Escape with Outdoor Sauna

Newly renovated two bedroom, two bath cottage with four person barrel sauna at Swinging Bridge Reservoir, Sullivan County's largest motorboat lake. Updated amenities and mid-century and modern furniture provide a welcome respite from the city just 90 miles away. Take in the local scenery, catch a show at the Forestburgh Playhouse or stop into some of the local vineyards and restaurants. For a low key weekend, hang out by the fireplace playing some records and cooking a meal.

May 13 – 20

R4,347 ZAR per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 741 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Jul 5 – 12

R2,109 ZAR per night

Guest favorite

Home in Monticello

4.98 out of 5 average rating, 105 reviews

Secluded lakefront home With an EV charger

Welcome to your oasis on the Swiniging Bridge Reservoir! Only 90 minutes from NYC, but a world away. A complete glass wall facing the water allows guests to take in the views and sounds of a babbling brook that feeds into a motorboat lake. This brand new house sleeps 6 adults (or 4 adults and 3 children) and features a full kitchen, free WiFi, bedding, linens, and toiletries. A canoe and paddleboat are also available for your use!

Apr 10 – 17

R7,949 ZAR per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 677 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Feb 9 – 16

R2,520 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Monticello vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Monticello's top sights

Resorts World Catskills182 locals recommend

Monticello Casino16 locals recommend

Walmart Supercenter80 locals recommend

ShopRite of Monticello73 locals recommend

McDonald's3 locals recommend

Miss Monticello Diner17 locals recommend

Other great vacation rentals in Monticello

Guest favorite

Guesthouse in Olivebridge

4.97 out of 5 average rating, 224 reviews

Black Olive Cabin in the Woods - Secluded, Tiny

Jul 20 – 27

R2,918 ZAR per night

Guest favorite

Home in Monticello

4.94 out of 5 average rating, 117 reviews

Magical Lake House-Hot Tub-Deck-Outdoor Kitchen

Nov 14 – 21

R11,202 ZAR per night

Guest favorite

Home in Monticello

4.93 out of 5 average rating, 171 reviews

Dancing Feather: Cozy Lake-Front A-Frame Chalet

Jun 23 – 30

R5,760 ZAR per night

Guest favorite

Tent in Livingston Manor

4.97 out of 5 average rating, 110 reviews

Milkweed Camp - Glamping in the Catskills

Sep 21 – 28

R2,084 ZAR per night

Guest favorite

Apartment in Mountain Dale

4.96 out of 5 average rating, 155 reviews

Cute space in Catskills hotspot Mountain Dale

Oct 2 – 9

R2,772 ZAR per night

Guest favorite

Apartment in Monticello

4.81 out of 5 average rating, 52 reviews

Convenient Carriage House

Jun 16 – 23

R1,674 ZAR per night

Guest favorite

Tiny home in Monticello

5.0 out of 5 average rating, 15 reviews

Little red glamping cabin under the pines

Oct 30 – Nov 6

R2,278 ZAR per night

Guest favorite

Tiny home in Ellenville

5.0 out of 5 average rating, 35 reviews

Romantic 1900s schoolhouse

Jan 31 – Feb 7

R2,084 ZAR per night

Show all

Other great vacation rentals in Monticello

Guest favorite

Cabin in Smallwood

5.0 out of 5 average rating, 43 reviews

Peaceful Cabin near BethelWoods /Toronto Reservoir

Jun 11 – 18

R2,988 ZAR per night

Guest favorite

Cabin in Jeffersonville

5.0 out of 5 average rating, 57 reviews

BirchRidge A-Frame-Barrel Sauna-Fire Pit-King Bed

Nov 26 – Dec 3

R8,380 ZAR per night

Guest favorite

Cottage in Liberty

4.96 out of 5 average rating, 56 reviews

Barton bungalow cozy relaxation on 7private acres

Mar 5 – 12

R2,835 ZAR per night

Guest favorite

Cabin in Forestburgh

5.0 out of 5 average rating, 21 reviews

Spirit Cabin - Modern Lakefront Home, Pool & Sauna

May 1 – 8

R8,646 ZAR per night

Guest favorite

Cabin in Woodridge

5.0 out of 5 average rating, 58 reviews

Escape to a 3-Bedroom Cabin in Lower Catskills

Dec 9 – 16

R2,885 ZAR per night

Guest favorite

Cabin in Mountain Dale

5.0 out of 5 average rating, 12 reviews

Foxtrot 1! Enjoy Your Serene Catskills Retreat!

Sep 19 – 26

R2,659 ZAR per night

Guest favorite

Cottage in Swan Lake

4.93 out of 5 average rating, 28 reviews

Tiny Home Near Woodstock

May 20 – 27

R2,857 ZAR per night

Superhost

Cabin in Monticello

4.85 out of 5 average rating, 26 reviews

Quiet Catskill Cabin near Bethel Woods, Lakes

Jul 14 – 21

R2,517 ZAR per night

Show all

Quick stats about vacation rentals in Monticello

Total rentals
60 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1K reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Monticello?
Yes! Work meets play with ease at over 40 vacation rentals in Monticello featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Monticello?
Four-legged friends are welcome in Monticello. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there Monticello vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Monticello, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Monticello?
Monticello has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do resort rentals in Monticello have a gym?
Absolutely! We offer over 30 resort rentals with a gym in Monticello. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Monticello have wifi?
Absolutely! We offer over 10 house rentals with wifi in Monticello. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Monticello?
Experience the best of Monticello with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Monticello have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Monticello. Enjoy a tailored experience with all the comforts you desire.

Monticello vacation rentals

Top-rated vacation rentals in Monticello

Vacation rentals for every style

Cabins

Hotels

Unique stays

Popular amenities for Monticello vacation rentals

Stay near Monticello's top sights

Other great vacation rentals in Monticello

Guesthouse in Olivebridge

Home in Monticello

Home in Monticello

Tent in Livingston Manor

Apartment in Mountain Dale

Apartment in Monticello

Tiny home in Monticello

Tiny home in Ellenville

Other great vacation rentals in Monticello

Cabin in Smallwood

Cabin in Jeffersonville

Cottage in Liberty

Cabin in Forestburgh

Cabin in Woodridge

Cabin in Mountain Dale

Cottage in Swan Lake

Cabin in Monticello

Quick stats about vacation rentals in Monticello

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Monticello?

Are there pet-friendly vacation rentals in Monticello?

Are there Monticello vacation rentals on Airbnb with pools?

Are there family-friendly house rentals in Monticello?

Do resort rentals in Monticello have a gym?

Do house rentals in Monticello have wifi?

How much does it cost to stay in house rentals in Monticello?

Do apartment rentals in Monticello have air conditioning?

Destinations to explore