Winchester Vacations from $279

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Your Winchester Vacation

Book a Winchester vacation package and discover the rhythm and way of life of this fascinating neighborhood. With all your travel plans worked out, the only thing you need to focus on here is having a great time. Kick start your trip to Winchester by checking out nearby attractions such as Boulder Station Casino, Boulder Station Hotel and Casino Bingo Room and Las Vegas Country Club. Stop daydreaming and start doing. When you're ready to book your dream vacation to Winchester, Expedia will help get you there.

The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

4 out of 5
Spring Valley
Save 100% on your flight
Price was $500, price is now $279 per person
$279
per person
Apr 27 - May 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Las Vegas (LAS)
8.8/10 Excellent! (1,001 reviews)
Very beautiful and clean place to stay

Reviewed on Mar 9, 2026

Harrah’s Las Vegas – A Caesars Rewards Destination

Harrah’s Las Vegas – A Caesars Rewards Destination

3.5 out of 5
Las Vegas Strip
Save 100% on your flight
Price was $1,389, price is now $642 per person
$642
per person
May 20 - May 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Las Vegas (LAS)
8/10 Very Good! (14,855 reviews)
Room was clean and beds were comfortable

Reviewed on Mar 16, 2026

One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite

One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite

4.5 out of 5
Price was $3,309, price is now $1,743 per person
$1,743
per person
May 20 - May 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Las Vegas (LAS)
7/10 Good! (2 reviews)
Staff was awesome and helpful

Reviewed on Sep 2, 2025

Vista Balcony Bliss Palms Place Strip Suite Hotel/Resort & Casino

Vista Balcony Bliss Palms Place Strip Suite Hotel/Resort & Casino

4.5 out of 5
Save 100% on your flight
Price was $2,555, price is now $1,393 per person
$1,393
per person
May 20 - May 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Las Vegas (LAS)
5.8/10 (8 reviews)
My room was very quiet and I enjoyed having the kitchen amenities and the balcony. The bed was average. My only negative comments are related to the unusually excessive daily damage deposit that I wasn’t expecting - big upfront unexpected expense! Also there was no bus cart for me to take groceries up to my room - but the bellmen would do it for a set fee. The pool was lovely, but closed at 7pm, which seemed early to me for summer. I enjoyed my stay, but won’t probably return to this resort.

Reviewed on Aug 4, 2025

Planet Hollywood Resort & Casino

Planet Hollywood Resort & Casino

4 out of 5
Las Vegas Strip
Save 100% on your flight
Price was $1,314, price is now $731 per person
$731
per person
May 20 - May 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Las Vegas (LAS)
8.2/10 Very Good! (21,771 reviews)
The room smells cigarette. Not well maintained.

Reviewed on Mar 16, 2026

Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
Miracle Mile Shops featuring night scenes, a casino and signage

Las Vegas Strip

5 out of top 10 points of interest in this area
4/5(59,675 area reviews)

Experience the dazzling lights, contemporary architecture, and diverse attractions of this iconic destination. Indulge in celebrity chef dining, catch a Cirque du Soleil show, and explore the highly walkable area with convenient transport options.

Find hotels in Las Vegas Strip

Winchester Hotel Deals

Excalibur Hotel & Casino

Excalibur Hotel & Casino

3.5 out of 5
3850 Las Vegas Blvd S Las Vegas NV
$58 nightly
The price is $65 total per night from Mar 17 to Mar 18
$65 total
Mar 17 - Mar 18
Total with taxes and fees
8/10 Very Good! (41,615 reviews)
The Hotel is located close to everything, and this makes your life easier in Vegas.

Reviewed on Mar 16, 2026

Excalibur Hotel & Casino
Treasure Island - TI Las Vegas Hotel & Casino

Treasure Island - TI Las Vegas Hotel & Casino

4 out of 5
3300 Las Vegas Blvd S Las Vegas NV
$85 nightly
The price is $96 total per night from Apr 5 to Apr 6
$96 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (32,975 reviews)
This hotel is a little outdated but in a good location. Staff was very helpful and kind.

Reviewed on Mar 16, 2026

Treasure Island - TI Las Vegas Hotel & Casino
The Venetian Resort Las Vegas

The Venetian Resort Las Vegas

5 out of 5
3355 Las Vegas Blvd S Las Vegas NV
$182 nightly
The price is $207 total per night from Mar 22 to Mar 23
$207 total
Mar 22 - Mar 23
Total with taxes and fees
9.2/10 Wonderful! (17,037 reviews)
My entire experience at this hotel was outstanding!

Reviewed on Mar 16, 2026

The Venetian Resort Las Vegas
See all 8,074 properties in Winchester
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 Winchester

Bellagio Casino

Bellagio Casino

This world-famous hotel is home to gorgeous botanical gardens, a unique glass sculpture and an elaborate fountain show.

Bellagio Casino
Fremont Street featuring interior views

Fremont Street

Stroll along the first paved street in Las Vegas to enjoy the neon lights, vibrant bars and non-stop gaming and entertainment that the city is famous for.

Fremont Street
Monorail at the Las Vegas Convention Center

Las Vegas Convention Center

During your trip, find out what's happening at Las Vegas Convention Center, a top convention center in Las Vegas. Make time to visit the area's casinos, or simply enjoy its lively bars.

Las Vegas Convention Center

Things to do

Las Vegas: The Sphere Experience — The Wizard of Oz

Las Vegas: The Sphere Experience — The Wizard of Oz

$114
per adult
92% of travellers recommend
Las Vegas: The Sphere Experience — The Wizard of Oz
Linq Hotel Promo Image

Fly LINQ Zipline

$38
per adult
80% of travellers recommend
Fly LINQ Zipline
Las Vegas: Universal Horror Unleashed

Universal Horror Unleashed

$76
per adult
Universal Horror Unleashed
See all activities in Las Vegas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.