Upper Montclair Holiday Rentals
New
House
- Newark
- ·
- Glen Ridge
- 0.19 mi to center
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
Parking
Kitchen
Air Conditioner
Internet
US $143/Night
7 Nights - US $1,004
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
9 Guests
742.71 ft²
- Parking
View- Air Conditioner
- Internet
US $357/Night
7 Nights - US $2,499
Hotel
9.6Exceptional
(519 Reviews)
1 Bath
Breakfast- Parking
- Air Conditioner
- Internet
US $562/Night
7 Nights - US $3,932
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $279/Night
7 Nights - US $1,950
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
990.28 ft²
- View
- Air Conditioner
- Internet
- Child Friendly
US $329/Night
7 Nights - US $2,305
New
Apartment
- Newark
- ·
- Bloomfield
- 0.06 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $165/Night
7 Nights - US $1,152
New
House
- New Jersey
- ·
- Verona
- 0.9 mi to center
6 Bedrooms
3 Baths
12 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $2,000/Night
7 Nights - US $14,003
New
House
- Newark
- ·
- Glen Ridge
- 0.17 mi to center
7 Bedrooms
3 Baths
14 Guests
Hot Tub- Air Conditioner
- Internet
- Child Friendly
US $1,696/Night
7 Nights - US $11,875
Apartment
- New Jersey
- ·
- Nutley
- 0.88 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
3 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $246/Night
7 Nights - US $1,721
Luxury Holiday Rentals in Upper Montclair
Over 137+ Luxury Holiday Rentals in or Near Upper Montclair
House
- Newark
- ·
- Upper Montclair
- 0.54 mi to center
3 Bedrooms
3 Baths
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $6,329/Night
7 Nights - US $44,303
House
5 Bedrooms
3 Baths
12 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $5,711/Night
7 Nights - US $39,976
New
House
- New Jersey
- ·
- Nutley
- 0.63 mi to center
3 Bedrooms
2 Baths
20 Guests
1700 ft²
- Hot Tub
- Parking
Balcony/Terrace- Kitchen
US $3,110/Night
7 Nights - US $21,771
New
House
- New Jersey
- ·
- Nutley
- 0.85 mi to center
3 Bedrooms
2 Baths
7 Guests
- Hot Tub
- Balcony/Terrace
- Air Conditioner
- Internet
US $2,521/Night
7 Nights - US $17,647
New
House
- Newark
- ·
- Upper Montclair
- 0.23 mi to center
5 Bedrooms
4 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,328/Night
7 Nights - US $16,295
House
- Jersey City
- ·
- Clifton
- 1.21 mi to center
4 Bedrooms
1 Bath
10 Guests
Private Pool- Parking
Pool
Ocean View
US $2,169/Night
7 Nights - US $15,184
House
- Newark
- ·
- Upper Montclair
- 0.44 mi to center
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $2,118/Night
7 Nights - US $14,827
House
- New Jersey
- ·
- Verona
- 0.53 mi to center
4 Bedrooms
3 Baths
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $2,066/Night
7 Nights - US $14,459
House
- Jersey City
- ·
- Clifton
- 1.71 mi to center
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Air Conditioner
- Internet
- Child Friendly
US $1,984/Night
7 Nights - US $13,891
Top-Rated Holiday Rentals with a Pool in Upper Montclair
Over 7+ The Best Private Villas and Holiday Rentals in Upper Montclair with a Pool
House
10.0Exceptional
(1 Review)
5 Bedrooms
2 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $1,445/Night
7 Nights - US $10,118
Hotel
- Newark
- ·
- West Orange
- 2.53 mi to center
8.8Fabulous
(735 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $222/Night
7 Nights - US $1,557
Hotel
- Newark
- ·
- West Orange
- 2.52 mi to center
8.4Excellent
(196 Reviews)
4 Baths
519.36 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
US $232/Night
7 Nights - US $1,624
House
- Jersey City
- ·
- Clifton
- 1.43 mi to center
5.0Average
(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Private Pool
- Pool
- Child Friendly
Bedding/Linens
US $275/Night
7 Nights - US $1,925
House
6 Bedrooms
4 Baths
12 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $704/Night
7 Nights - US $4,928
House
- Newark
- ·
- Upper Montclair
- 0.55 mi to center
4 Bedrooms
4 Baths
10 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $575/Night
7 Nights - US $4,025
Apartment
- New Jersey
- ·
- Cedar Grove
- 0.94 mi to center
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $100/Night
7 Nights - US $700
Pet-Friendly Holiday Rentals in Upper Montclair
Over 41+ Pet-Friendly Holiday Rentals in or Near Upper Montclair
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $509/Night
7 Nights - US $3,561
Apartment
- Newark
- ·
- Glen Ridge
- 0.47 mi to center
9.8Exceptional
(6 Reviews)
5 Bedrooms
4 Baths
13 Guests
13993.08 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $225/Night
7 Nights - US $1,575
Hotel
8.8Fabulous
(609 Reviews)
1 Bath
- Breakfast
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $377/Night
7 Nights - US $2,640
Apartment
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $363/Night
7 Nights - US $2,542
Apartment
- Newark
- ·
- Bloomfield
- 1.24 mi to center
9.2Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
8 Guests
979.52 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $225/Night
7 Nights - US $1,575
Apartment
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $301/Night
7 Nights - US $2,107
Apartment
- Jersey City
- ·
- Clifton
- 0.63 mi to center
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $143/Night
7 Nights - US $999
Apartment
- Jersey City
- ·
- Clifton
- 0.57 mi to center
1 Bedroom
1 Bath
2 Guests
600 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $141/Night
7 Nights - US $986
Apartment
- Jersey City
- ·
- Clifton
- 0.61 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $135/Night
7 Nights - US $942
Large Holiday Rentals and Private Villas in Upper Montclair
Over 22+ Large Holiday Rentals and Private Villas in or Near Upper Montclair
House
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
11 Guests
2200 ft²
- Ocean View
- View
- Kitchen
- Air Conditioner
US $1,234/Night
7 Nights - US $8,638
Apartment
9.8Exceptional
(5 Reviews)
6 Bedrooms
4 Baths
13 Guests
1194.79 ft²
- Breakfast
- Parking
- View
- Air Conditioner
US $340/Night
7 Nights - US $2,381
Apartment
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,004/Night
7 Nights - US $7,029
Apartment
9.7Exceptional
(3 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $339/Night
7 Nights - US $2,370
House
- Newark
- ·
- Upper Montclair
- 0.76 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
10 Guests
1650 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $987/Night
7 Nights - US $6,909
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
11 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $878/Night
7 Nights - US $6,143
House
- Newark
- ·
- Upper Montclair
- 0.88 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $621/Night
7 Nights - US $4,348
House
9.6Exceptional
(13 Reviews)
6 Bedrooms
3 Baths
12 Guests
2500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $585/Night
7 Nights - US $4,095
House
- Newark
- ·
- Upper Montclair
- 0.82 mi to center
9.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,188/Night
7 Nights - US $8,318
Wheelchair Accessible Holiday Homes in Upper Montclair
Over 1+ Wheelchair Accessible Holiday Homes in or Near Upper Montclair
Hotel
- Jersey City
- ·
- Clifton
- 2.00 mi to center
7.0Very Good
(462 Reviews)
1 Bath
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $99/Night
7 Nights - US $693
Upper Montclair Private Villas and Holiday Homes Under $200
Over 35+ Upper Montclair Private Villas and Holiday Homes Under $200
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $146/Night
7 Nights - US $1,025
House
- Newark
- ·
- Glen Ridge
- 0.19 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
699.65 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
US $130/Night
7 Nights - US $910
Condo
9.6Exceptional
(68 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $191/Night
7 Nights - US $1,339
Apartment
9.8Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- Air Conditioner
- Internet
- Child Friendly
- Security/Safety
US $157/Night
7 Nights - US $1,099
Apartment
- Newark
- ·
- Bloomfield
- 0.83 mi to center
1 Bedroom
1 Bath
2 Guests
600 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $126/Night
7 Nights - US $881
Apartment
8.6Fabulous
(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,319
Apartment
- New Jersey
- ·
- Verona
- 0.38 mi to center
2 Bedrooms
1 Bath
3 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $128/Night
7 Nights - US $894
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $154/Night
7 Nights - US $1,078
House
- Newark
- ·
- Glen Ridge
- 0.19 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $200/Night
7 Nights - US $1,400
Instantly Bookable Holiday Homes in Upper Montclair
Over 53+ Instantly Bookable Holiday Homes in or Near Upper Montclair
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
740 ft²
- Parking
- Ocean View
- View
- Kitchen
US $341/Night
7 Nights - US $2,388
New
House
- Newark
- ·
- Bloomfield
- 0.41 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $278/Night
7 Nights - US $1,947
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
1300 ft²
- Ocean View
- View
- Kitchen
- Air Conditioner
US $353/Night
7 Nights - US $2,473
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $344/Night
7 Nights - US $2,407
Apartment
9.8Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
990 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $406/Night
7 Nights - US $2,843
Apartment
9.8Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $354/Night
7 Nights - US $2,477
House
9.8Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $481/Night
7 Nights - US $3,370
Apartment
9.8Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $235/Night
7 Nights - US $1,642
House
9.6Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $392/Night
7 Nights - US $2,742
Book a Last Minute Place to Stay in Upper Montclair
About Casai's Private Villas and Holiday Rentals in Upper Montclair
Discover more than 146 vacation rentals available in Upper Montclair. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Upper Montclair.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Upper Montclair, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Upper Montclair. On average, places to stay near Upper Montclair offer 550.47 ft², with nightly prices averaging US $692.
With Casai, finding and comparing holiday rentals in Upper Montclair is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Upper Montclair
| Type | Count |
|---|---|
| Holiday Apartments | 67 |
| Vacation Homes | 64 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Upper Montclair
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Upper Montclair.
Weather in Upper Montclair, NJ
View the weather forecast for Upper Montclair before booking your Upper Montclair Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in Upper Montclair, NJ
Frequently Asked Questions About Upper Montclair?
What are the top holiday rentals in Upper Montclair?
With numerous options available in Upper Montclair, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Upper Montclair:
- Charming 3-bedroom 1.5 bth apartment steps from train to NYC in lovely Montclair
- Steps to NYC Train! Charming Carriage House Loft
- Modern living
- Chic 2BR w/Urban Patio + Walk to NYC Transit
- Lovely 1 BD downtown 2F apt in quite neighborhood
- Charming & stylish Victorian Farmhouse with lots of amenities!
- Clean, Classy, Convenient. Montclair's Best Stay! Walk to town and train
- Charming Apt Walkable to Shop, Eat & NYC Transport
- Apartment located in vibrant Montclair 2-blocks to NYC trains
- The Baldwin NJ- The Best Stay for MAJOR INTERNATIONAL SPORTING EVENT 2026
Which holiday homes in Upper Montclair are best for families?
If you're searching for a family-friendly holiday home in Upper Montclair, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Upper Montclair:
- Lovely 1 BD downtown 2F apt in quite neighborhood
- 7 Mi to Newark: Montclair Vacation Rental
- Urban Suite
How many Casai.com holiday rentals are available in Upper Montclair?
As of 2026, Casai boasts over 146 properties listed in the Upper Montclair area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Upper Montclair.
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