Overland Trail Vacations from $288

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Your Overland Trail Vacation

Overland Trail is calling! Whatever type of escape you have in mind, you can discover more of this neighborhood with an Overland Trail vacation package. Eager to get out and see the sights during your trip to Overland Trail? Make sure you check out nearby attractions such as Six Flags Hurricane Harbor Phoenix, Victory Lane Sports Complex and The Legend at Arrowhead. Expedia can help you turn your dream Overland Trail vacation into reality, whatever your budget or travel plans.

The Latest Overland Trail Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Pinon Pointe, Sedona

Hyatt Vacation Club at Pinon Pointe, Sedona

3.5 out of 5
Uptown Sedona
Save 100% on your flight
Price was $506, price is now $288 per person
$288
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Phoenix (PHX)
8.8/10 Excellent! (1,000 reviews)
Everything was good

Reviewed on Dec 5, 2025

Raintree at Phoenix South Mountain Preserve

Raintree at Phoenix South Mountain Preserve

3.5 out of 5
South Mountain
Price was $906, price is now $406 per person
$406
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Phoenix (PHX)
8.4/10 Very Good! (130 reviews)
Spacious condo in timeshare resort. Staff was efficient and friendly. Grounds were clean. Units themselves are pretty dated and look like they were furnished in the 70s. Better than staying at a mid range hotel in the area for the money.

Reviewed on Nov 9, 2025

Mountain Shadows Resort Scottsdale

Mountain Shadows Resort Scottsdale

4.5 out of 5
Save 100% on your flight
Price was $1,755, price is now $1,021 per person
$1,021
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Phoenix (PHX)
9.8/10 Exceptional! (1,012 reviews)
The property was well kept!!! The adult pool bar staff was truly accommodating and making sure you were served at the poolside (and also while in the pool😃). The bartender, Cat (at the main hotel bar), was very communicative and friendly!!!! Will definitely stay here again!!!

Reviewed on Dec 8, 2025

Hotel Valley Ho

Hotel Valley Ho

4.5 out of 5
Old Town
Save 100% on your flight
Price was $1,403, price is now $830 per person
$830
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Phoenix (PHX)
9.6/10 Exceptional! (2,097 reviews)
We loved our stay! We wish we would have gotten the suite we thought we booked, also we were unaware of one of the pools being shut down for the holiday - but overall we had an amazing time! The staff is so friendly and all smiles.

Reviewed on Dec 8, 2025

Adobe Grand Villas

Adobe Grand Villas

4 out of 5
West Sedona
Save 100% on your flight
Price was $1,911, price is now $1,134 per person
$1,134
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Phoenix (PHX)
10/10 Exceptional! (458 reviews)
Our stay started very well and by the time we left the room was filthy lack of really caring about the room. Maria was very nice. The rest of the staff were nice, but I would give it an average.

Reviewed on Nov 18, 2025

Where to stay in Overland Trail

Find the best Overland Trail areas and neighborhoods for the activities you enjoy most. Learn more about Overland Trail
Downtown Phoenix which includes signage and night scenes

Downtown Phoenix

2 out of top 10 points of interest in this area
3.5/5(2,458 area reviews)

A true urban neighborhood, Downtown Phoenix boasts major sports venues like Chase Field and Footprint Center, as well as cultural attractions such as the Arizona Science Center and Phoenix Art Museum. Easily accessible via Valley Metro Light Rail, enjoy walkable streets, friendly cafes, and local businesses.

Find hotels in Downtown Phoenix

Overland Trail Hotel Deals

Talking Stick Resort

Talking Stick Resort

4 out of 5
9800 E. Talking Stick Way Scottsdale AZ
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $210 total per night from Dec 14 to Dec 15
$210 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (4,149 reviews)
Clean room great staff

Reviewed on Dec 5, 2025

Talking Stick Resort
Hilton Phoenix Tapatio Cliffs Resort

Hilton Phoenix Tapatio Cliffs Resort

4 out of 5
11111 N 7th St Phoenix AZ
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $164 total per night from Dec 21 to Dec 22
$164 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,203 reviews)
I fell off

Reviewed on Dec 7, 2025

Hilton Phoenix Tapatio Cliffs Resort
Hilton Garden Inn Phoenix Airport North

Hilton Garden Inn Phoenix Airport North

3 out of 5
3838 E Van Buren St Phoenix AZ
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $95 total per night from Dec 21 to Dec 22
$95 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (2,278 reviews)
Nice hotel. Clean room.

Reviewed on Dec 10, 2025

Hilton Garden Inn Phoenix Airport North
See all 12,396 properties in Overland Trail
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 Overland Trail

Grady Gammage Memorial Auditorium

Arizona State University

4.5/5(1,877 reviews)

Explore the campus of Arizona State University, a top college in Tempe. Amble around the area's lakeside or seek out the jogging trails.

Arizona State University
Phoenix Convention Center

Phoenix Convention Center

4/5(959 reviews)

During your trip, find out what's happening at Phoenix Convention Center, a top convention center in Phoenix. Experience the acclaimed art scene and fascinating museums in this vibrant area.

Phoenix Convention Center
Gameday in Glendale, AZ.

State Farm Stadium

4.5/5(934 reviews)

Catch an event at State Farm Stadium during your trip to Glendale. Experience the lively festivals or attend a football game in this culturally rich area.

State Farm Stadium

Things to do

Phoenix: Historic Walking Tour

Phoenix: Historic Walking Tour

$25
per adult
Phoenix: Historic Walking Tour
See all activities in Phoenix
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.