Upper Montclair Vacations from $231

Book a Hotel + Flight or Car together to unlock savings

Photo by Michele McLaughlin Di Sanza

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Upper Montclair Vacation

Reserving a tailor-made Upper Montclair vacation package is an excellent way to become familiar with this neighborhood. From its hot spots to its lesser-known delights, there's plenty to discover. Some top nearby attractions to check out during your trip to Upper Montclair include Wellmont Theatre, Montclair Art Museum and Van Vleck House & Gardens. Expedia can help turn your dream Upper Montclair vacation into reality, no matter your budget or travel plans.

The Latest Upper Montclair Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $362, price is now $231 per person
$231
per person
Feb 19 - Feb 22
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (227 reviews)
Room was spacious, spotless and comfortable. Kristofer was so polite and helpful. Hotel was in a safe area near plenty of restaurants.abd

Reviewed on Jan 11, 2026

Casa Francesca 6BR Villa & Heated Pool

Casa Francesca 6BR Villa & Heated Pool

3.5 out of 5
Save 100% on your flight
Price was $4,960, price is now $3,157 per person
$3,157
per person
Apr 3 - Apr 8
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
No reviews
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $1,551, price is now $998 per person
$998
per person
Mar 22 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (7 reviews)
The staff is lovely and the property gorgeous. The room could have been more complete (no slippers to be found and no in-room mini bar amenities, which was surprising). The grounds are pristine and peaceful.

Reviewed on Jun 13, 2025

Madison Hotel

Madison Hotel

4 out of 5
Save 100% on your flight
Price was $602, price is now $396 per person
$396
per person
Feb 14 - Feb 18
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Comfortable room, great breakfast, nice staff, great fireplace lobby.

Reviewed on Jan 3, 2026

Mountain Springs Lake Resort

Mountain Springs Lake Resort

3.5 out of 5
Save 100% on your flight
Price was $632, price is now $418 per person
$418
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (234 reviews)
Everything was amazing

Reviewed on Jan 12, 2026

Upper Montclair Hotel Deals

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
811 7th Ave New York NY
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $217 total per night from Feb 8 to Feb 9
$217 total
Feb 8 - Feb 9
Total with taxes and fees
7.2/10 Good! (6,431 reviews)
Claudia was great, keep her there for customer satisfaction

Reviewed on Jan 11, 2026

Sheraton New York Times Square Hotel
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street New York NY
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $212 total per night from Jan 17 to Jan 18
$212 total
Jan 17 - Jan 18
Total with taxes and fees
8.2/10 Very Good! (6,406 reviews)
Shower water pressure was lower than one would wish for. Otherwise excellent stay

Reviewed on Jan 12, 2026

Hyatt Grand Central New York
Hyatt Regency Times Square

Hyatt Regency Times Square

3.5 out of 5
1605 Broadway New York NY
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $224 total per night from Jan 19 to Jan 20
$224 total
Jan 19 - Jan 20
Total with taxes and fees
8.6/10 Excellent! (231 reviews)
The room was a little warm and hard to get the temperature down even with the heat off. Window opens but then a little loud (sirens) throughout the night. Only complaint. Staff were all amazing and helpful rooms were nice and update and clean! Would stay here again.

Reviewed on Jan 7, 2026

Hyatt Regency Times Square
See all 12,077 properties in Upper Montclair
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Upper Montclair

Beautiful photo spot when in in bloom

Presby Memorial Iris Gardens

Explore the great outdoors at Presby Memorial Iris Gardens, a lovely green space in Montclair. Amble around this vibrant area's riverfront or experience its entertainment choices.

Presby Memorial Iris Gardens
Montclair Art Museum showing interior views and art

Montclair Art Museum

Use the audio guide to learn about historic and modern Native American art and sip wine at a live music event.

Montclair Art Museum
Van Vleck House & Gardens which includes a park

Van Vleck House & Gardens

Meander through these pretty gardens to appreciate the range of exotic specimens and attend a piano recital or art exhibit in the house.

Van Vleck House & Gardens

Things to do

New Jersey Devils Ice Hockey Game at Prudential Center

New Jersey Devils Ice Hockey Game at Prudential Center

$97
per adult
New Jersey Devils Ice Hockey Game at Prudential Center
American Dream: LEGOLAND Discovery Center New Jersey

American Dream: LEGOLAND Discovery Center New Jersey

$32
per traveler
100% of travellers recommend
American Dream: LEGOLAND Discovery Center New Jersey
New Jersey: American Dream Escape Room

New Jersey: American Dream Escape Room

$49
per adult
New Jersey: American Dream Escape Room
See all activities in Montclair
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.