Lexington Hills Vacations from $418

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Your Lexington Hills Vacation

Say farewell to planning worries and hello to a Lexington Hills vacation package. With the finer details organized before you take off, you can focus on discovering the best of this city, starting with South San Jose, which is good for culture, golfing and mountain biking. Every trip to Lexington Hills needs a well-planned itinerary. Fill yours with famous sights like Old Town Los Gatos, Testarossa Winery and Vasona Lake County Park. Expedia can help you escape your daily routine. Tailor your vacation to Lexington Hills to match your travel style, whatever that may be.

The Latest Lexington Hills vacation packages

Price found within the past 48 hours. Click for updated prices.
The Stevenson Monterey

The Stevenson Monterey

2.5 out of 5
Downtown Monterey
Save 100% on your flight
Price was $705, price is now $418 per person
$418
per person
Feb 4 - Feb 11
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Francisco (SFO)
8.8/10 Excellent! (1,004 reviews)
Friendly staff, clean room, parking on site, great location.

Reviewed on Dec 2, 2025

The Phoenix Hotel

The Phoenix Hotel

3 out of 5
Downtown San Francisco
Price was $1,125, price is now $567 per person
$567
per person
Jan 6 - Jan 13
found 1 day ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
9/10 Wonderful! (1,004 reviews)
Excellent customer service, aesthetic fantastic, beautiful details, one of a kind. You have to stay here at least once! Culturally iconic.

Reviewed on Nov 30, 2025

Montage Healdsburg

Montage Healdsburg

5 out of 5
Price was $2,060, price is now $1,086 per person
$1,086
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
9.6/10 Exceptional! (113 reviews)
Clean room, kind and helpful staff. Nice ambiance in vineyard.

Reviewed on Nov 30, 2025

Hotel Julian

Hotel Julian

3 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $1,492, price is now $913 per person
$913
per person
Jan 12 - Jan 14
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Francisco (SFO)
8.6/10 Excellent! (559 reviews)
Staff were great, the rooms ac wasn’t really cooling b

Reviewed on Nov 25, 2025

Hotel Healdsburg

Hotel Healdsburg

4 out of 5
Save 100% on your flight
Price was $783, price is now $486 per person
$486
per person
Jan 16 - Jan 18
just found
Roundtrip flight included
Orange County (SNA) to San Francisco (SFO)
9.2/10 Wonderful! (427 reviews)
Nice Hotel close to everything. Valet took care of us everyday. Bartender could use a little help in customer service, was a little rude on a couple occasions. All in all great stay and a nice hotel

Reviewed on Nov 23, 2025

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Discover the most popular places to visit in Lexington Hills

Vasona Lake County Park

Vasona Lake County Park

3.5/5(3 reviews)

Vasona Lake County Park is just one of the places to see in Los Gatos, so why not enjoy the other things to explore during your travels? Discover the mountain views and shops in this family-friendly area.

Vasona Lake County Park
Wonderful spot for wine tasting, private parties, or a picnic. Spacious Italian garden overlooks the vineyards and Santa Cruz mountains. Specializes in Pinot Noir. Turned to members only this past spring.

Regale Winery and Vineyards

You can enjoy a tasting or tour at Regale Winery and Vineyards during your travels to Los Gatos. Amble around this family-friendly area's beautiful beaches, or seek out the biking trails.

Regale Winery and Vineyards

Old Town Los Gatos

You can search for that perfect souvenir at Old Town Los Gatos during your trip to Los Gatos. Check out the shops and top-notch restaurants in this family-friendly area.

Old Town Los Gatos

What to do in Lexington Hills

Picture 2 for Activity San Jose: Valley Ghosts Haunted Walking Tour

San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette

$32
per adult
80% of travellers recommend
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
Silicon Valley Tech Tour

Silicon Valley Tech Tour

$185
per adult
Silicon Valley Tech Tour
Rock Climbing 2 - Beyond the Basics

Outdoor Rock Climbing - Level 2

$119
per adult
Outdoor Rock Climbing - Level 2
See all activities in Lexington Hills

Lexington Hills Hotel Deals

The Domain Hotel

The Domain Hotel

4 out of 5
1085 E El Camino Real Sunnyvale CA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $123 total per night from Dec 16 to Dec 17
$123 total
Dec 16 - Dec 17
Total with taxes and fees
8/10 Very Good! (1,366 reviews)
Yes

Reviewed on Nov 27, 2025

The Domain Hotel
Sonesta Silicon Valley

Sonesta Silicon Valley

4 out of 5
1820 Barber Ln Milpitas CA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $120 total per night from Dec 25 to Dec 26
$120 total
Dec 25 - Dec 26
Total with taxes and fees
9/10 Wonderful! (1,630 reviews)
Clean and updated. We enjoyed how friendly the staff was. Pool area is awesome. Breakfast buffett was good but a bit more limited than expected for a 4-star hotel. There was no change of menus from day to day.

Reviewed on Nov 23, 2025

Sonesta Silicon Valley
Maple Tree Inn

Maple Tree Inn

3 out of 5
711 E El Camino Real Sunnyvale CA
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $86 total per night from Dec 12 to Dec 13
$86 total
Dec 12 - Dec 13
Total with taxes and fees
9/10 Wonderful! (2,424 reviews)
Rooms were clean and comfortable. Staff was wonderful.

Reviewed on Nov 29, 2025

Maple Tree Inn
See all 2,957 properties in Lexington Hills
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.

Find the Best Lexington Hills Vacation Packages

Lexington Hills Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norman Y. Mineta San Jose Intl. Airport (SJC)
Population
2,400
Top Sights
Testarossa Winery, Regale Winery and Vineyards and Loma Prieta Winery

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Frequently asked questions

How much does a Lexington Hills vacation package cost?
Offering excellent value package deals from $418 on Expedia, you'll be pleasantly surprised at how much a vacation to Lexington Hills costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Lexington Hills?
You can generally find lower prices and greater availability in January, October and December. Explore our cheap Lexington Hills vacation packages and you could score some great off-season discounts.
How many days is enough for Lexington Hills?
With a well-organized travel plan, you can easily tick off the most popular Lexington Hills sights in a handful of days. But if you prefer to explore off the beaten track or take day trips, think about booking your Lexington Hills vacation for longer.
How to find the best Lexington Hills package deals?
Landing a cheap Lexington Hills package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Lexington Hills package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Lexington Hills vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Lexington Hills vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Lexington Hills?
If you're planning a spontaneous Lexington Hills adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Lexington Hills vacation packages?
Set off on your perfect escape to Lexington Hills with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until your next payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.